Aspirin

Identification

Summary

Aspirin is a salicylate used to treat pain, fever, inflammation, migraines, and reducing the risk of major adverse cardiovascular events.

Brand Names

Aggrenox, Alka-seltzer, Alka-seltzer Fruit Chews, Anacin, Arthriten Inflammatory Pain, Ascomp, Aspi-cor, Aspir-low, Bayer Aspirin, Bayer Womens, Bc Arthritis, Bc Original Formula, Bufferin, Duoplavin, Durlaza, Ecotrin, Ecpirin, Endodan Reformulated May 2009, Equagesic, Exaprin, Excedrin, Excedrin PM Triple Action, Fasprin, Fiorinal, Goody's Body Pain, Goody's Extra Strength, Goody's PM, Miniprin, Norgesic, Norgesic Forte, Orphengesic, Pamprin Max Formula, Robaxisal, ST. Joseph Aspirin, Stanback Headache Powder Reformulated Jan 2011, Trianal, Trianal C, Vanquish, Vazalore, Yosprala

Generic Name

Acetylsalicylic acid
Commonly known or available as Aspirin

DrugBank Accession Number

DB00945

Background

Also known as Aspirin, acetylsalicylic acid (ASA) is a commonly used drug for the treatment of pain and fever due to various causes. Acetylsalicylic acid has both anti-inflammatory and antipyretic effects. This drug also inhibits platelet aggregation and is used in the prevention of blood clots stroke, and myocardial infarction (MI) ^Label.

Interestingly, the results of various studies have demonstrated that long-term use of acetylsalicylic acid may decrease the risk of various cancers, including colorectal, esophageal, breast, lung, prostate, liver and skin cancer ¹⁵. Aspirin is classified as a non-selective cyclooxygenase (COX) inhibitor ^11,14 and is available in many doses and forms, including chewable tablets, suppositories, extended release formulations, and others ¹⁹.

Acetylsalicylic acid is a very common cause of accidental poisoning in young children. It should be kept out of reach from young children, toddlers, and infants ^Label.

Type

Small Molecule

Groups

Approved, Vet approved

Structure

Similar Structures

Weight: Average: 180.1574
Monoisotopic: 180.042258744
Chemical Formula: C₉H₈O₄

Synonyms

2-Acetoxybenzenecarboxylic acid
2-Acetoxybenzoic acid
Acetylsalicylate
Acetylsalicylsäure
acide 2-(acétyloxy)benzoïque
Acide acétylsalicylique
ácido acetilsalicílico
Acidum acetylsalicylicum
ASA
Aspirin
Aspirina
Azetylsalizylsäure
o-acetoxybenzoic acid
O-acetylsalicylic acid
o-carboxyphenyl acetate
Polopiryna
Salicylic acid acetate

External IDs

BAY1019036
NSC-27223
NSC-406186

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Pharmacology

Indication

Pain, fever, and inflammation

Acetylsalicylic acid (ASA), in the regular tablet form (immediate-release), is indicated to relieve pain, fever, and inflammation associated with many conditions, including the flu, the common cold, neck and back pain, dysmenorrhea, headache, tooth pain, sprains, fractures, myositis, neuralgia, synovitis, arthritis, bursitis, burns, and various injuries. It is also used for symptomatic pain relief after surgical and dental procedures ^Label.

The extra strength formulation of acetylsalicylic acid is also indicated for the management migraine pain with photophobia (sensitivity to light) and phonophobia (sensitivity to sound)^Label.

Other indications

ASA is also indicated for various other purposes, due to its ability to inhibit platelet aggregation. These include:

Reducing the risk of cardiovascular death in suspected cases of myocardial infarction (MI) ^Label.

Reducing the risk of a first non-fatal myocardial infarction in patients, and for reducing the risk of morbidity and mortality in cases of unstable angina and in those who have had a prior myocardial infarction ^Label.

For reducing the risk of transient ischemic attacks (TIA) and to prevent atherothrombotic cerebral infarction (in conjunction with other treatments) ^Label.

For the prevention of thromboembolism after hip replacement surgery ^Label.

For decreasing platelet to platelet adhesion following carotid endarterectomy, aiding in the prevention of transient ischemic attacks (TIA) ^Label.

Used for patients undergoing hemodialysis with a silicone rubber arteriovenous cannula inserted to prevent thrombosis at the insertion site ^Label.

Important note regarding use of the extended-release formulation ²²

In the setting of acute myocardial infarction, or before percutaneous interventions, the extended-release form of acetylsalicylic acid should not be used. Use immediate-release formulations in scenarios requiring rapid onset of action ^Label,22. The extended-release form is taken to decrease the incidence of mortality and myocardial infarction (MI) for individuals diagnosed with chronic coronary artery disease (CAD), including patients with previous myocardial infarction (MI) or unstable angina or with chronic stable angina. Additionally, the extended-release form is used to decrease the risk of death and recurrent episodes of stroke in patients with a history of stroke or TIA ²².

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Dose Form
Treatment of	Acute coronary syndrome (acs)		••• •••••
Used in combination to manage	Anxiety	Combination Product in combination with: Meprobamate (DB00371)	••• •••••
Symptomatic treatment of	Arthritis		••••••••••••	••••••• •••••••• •••••••• ••••••• ••••••••• ••••••• ••••••• •••••• ••••••••••••••• ••••••• ••••••• ••••••• •••• ••••••
Prevention of	Atherothrombotic cerebral infarction		••••••••••••
Prevention of	Cardiovascular disease		••• •••••

Associated Therapies

Contraindications & Blackbox Warnings

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Pharmacodynamics

Effects on pain and fever

Acetylsalicylic acid disrupts the production of prostaglandins throughout the body by targeting cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) ^9,10,11. Prostaglandins are potent, irritating substances that have been shown to cause headaches and pain upon injection into humans. Prostaglandins increase the sensitivity of pain receptors and substances such as histamine and bradykinin. Through the disruption of the production and prevention of release of prostaglandins in inflammation, this drug may stop their action at pain receptors, preventing symptoms of pain. Acetylsalicylic acid is considered an antipyretic agent because of its ability to interfere with the production of brain prostaglandin E1. Prostaglandin E1 is known to be an extremely powerful fever-inducing agent ^Label.

Effects on platelet aggregation

The inhibition of platelet aggregation by ASA occurs because of its interference with thromboxane A2 in platelets, caused by COX-1 inhibition. Thromboxane A2 is an important lipid responsible for platelet aggregation, which can lead to clot formation and future risk of heart attack or stroke ^Label.

A note on cancer prevention

ASA has been studied in recent years to determine its effect on the prevention of various malignancies ¹⁵. In general, acetylsalicylic acid is involved in the interference of various cancer signaling pathways, sometimes inducing or upregulating tumor suppressor genes ^15,17. Results of various studies suggest that there are beneficial effects of long-term ASA use in the prevention of several types of cancer, including stomach, colorectal, pancreatic, and liver cancers ¹⁶. Research is ongoing.

Mechanism of action

Acetylsalicylic acid (ASA) blocks prostaglandin synthesis. It is non-selective for COX-1 and COX-2 enzymes ^9,10,11. Inhibition of COX-1 results in the inhibition of platelet aggregation for about 7-10 days (average platelet lifespan). The acetyl group of acetylsalicylic acid binds with a serine residue of the cyclooxygenase-1 (COX-1) enzyme, leading to irreversible inhibition. This prevents the production of pain-causing prostaglandins. This process also stops the conversion of arachidonic acid to thromboxane A2 (TXA2), which is a potent inducer of platelet aggregation ^Label. Platelet aggregation can result in clots and harmful venous and arterial thromboembolism, leading to conditions such as pulmonary embolism and stroke.

It is important to note that there is 60% homology between the protein structures of COX-1 and COX-2. ASA binds to serine 516 residue on the active site of COX-2 in the same fashion as its binding to the serine 530 residue located on the active site of COX-1. The active site of COX-2 is, however, slightly larger than the active site of COX-1, so that arachidonic acid (which later becomes prostaglandins) manages to bypass the aspirin molecule inactivating COX-2 ^11,12. ASA, therefore, exerts more action on the COX-1 receptor rather than on the COX-2 receptor ¹⁴. A higher dose of acetylsalicylic acid is required for COX-2 inhibition ¹⁵.

Target	Actions	Organism
AProstaglandin G/H synthase 1	inhibitor	Humans
AProstaglandin G/H synthase 2	inhibitor	Humans
UAldo-keto reductase family 1 member C1	inhibitor	Humans
U5'-AMP-activated protein kinase	activator	Humans
UEndothelin-1 receptor	inhibitor	Humans
UCellular tumor antigen p53	inducer	Humans
U78 kDa glucose-regulated protein	inhibitor binder	Humans
URibosomal protein S6 kinase alpha-3	inhibitor	Humans
UNF-kappa-B inhibitor alpha	inhibitor	Humans
UTumor necrosis factor-inducible gene 6 protein	inhibitor downregulator	Humans
UCaspase-1	inhibitor downregulator	Humans
UCaspase-3	inhibitor downregulator	Humans
UInhibitor of nuclear factor kappa-B kinase subunit beta	Not Available	Humans
UExtracellular signal-regulated kinase (ERK)	Not Available	Humans
UG1/S-specific cyclin-D1	downregulator	Humans
UMyc proto-oncogene protein	downregulator	Humans
UProliferating cell nuclear antigen	downregulator	Humans
UCyclin A	downregulator
USialidase-1	inhibitor	Humans

Absorption

Absorption is generally rapid and complete following oral administration but absorption may be variable depending on the route, dosage form, and other factors including but not limited to the rate of tablet dissolution, gastric contents, gastric emptying time, and gastric pH ^Label.

Detailed absorption information

When ingested orally, acetylsalicylic acid is rapidly absorbed in both the stomach and proximal small intestine. The non-ionized acetylsalicylic acid passes through the stomach lining by passive diffusion. Ideal absorption of salicylate in the stomach occurs in the pH range of 2.15 - 4.10. Intestinal absorption of acetylsalicylic acid occurs at a much faster rate. At least half of the ingested dose is hydrolyzed to salicylic acid in the first-hour post-ingestion by esterases found in the gastrointestinal tract. Peak plasma salicylate concentrations occur between 1-2 hours post-administration ^Label.

Volume of distribution

This drug is distributed to body tissues shortly after administration. It is known to cross the placenta. The plasma contains high levels of salicylate, as well as tissues such as spinal, peritoneal and synovial fluids, saliva and milk. The kidney, liver, heart, and lungs are also found to be rich in salicylate concentration after dosing. Low concentrations of salicylate are usually low, and minimal concentrations are found in feces, bile, and sweat ^Label.

Protein binding

50% to 90% of a normal therapeutic concentration salicylate (a main metabolite of acetylsalicylic acid ^Label) binds plasma proteins, particularly albumin, while acetylsalicylic acid itself binds negligibly ^Label. Acetylsalicylic acid has the ability to bind to and acetylate many proteins, hormones, DNA, platelets, and hemoglobin ^Label.

Metabolism

Acetylsalicylic acid is hydrolyzed in the plasma to salicylic acid. Plasma concentrations of aspirin following after administration of the extended-release form are mostly undetectable 4-8 hours after ingestion of a single dose. Salicylic acid was measured at 24 hours following a single dose of extended-release acetylsalicylic acid ²².

Salicylate is mainly metabolized in the liver, although other tissues may also be involved in this process ^Label. The major metabolites of acetylsalicylic acid are salicylic acid, salicyluric acid, the ether or phenolic glucuronide and the ester or acyl glucuronide. A small portion is converted to gentisic acid and other hydroxybenzoic acids ^Label.

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Acetylsalicylic acid

Route of elimination

Excretion of salicylates occurs mainly through the kidney, by the processes of glomerular filtration and tubular excretion, in the form of free salicylic acid, salicyluric acid, and, additionally, phenolic and acyl glucuronides ^Label.

Salicylate can be found in the urine soon after administration, however, the entire dose takes about 48 hours to be completely eliminated. The rate of salicylate is often variable, ranging from 10% to 85% in the urine, and heavily depends on urinary pH. Acidic urine generally aids in reabsorption of salicylate by the renal tubules, while alkaline urine increases excretion ^Label.

After the administration of a typical 325mg dose, the elimination of ASA is found to follow first order kinetics in a linear fashion. At high concentrations, the elimination half-life increases ^Label.

Half-life

The half-life of ASA in the circulation ranges from 13 - 19 minutes. Blood concentrations drop rapidly after complete absorption. The half-life of the salicylate ranges between 3.5 and 4.5 hours ^Label.

Clearance

The clearance rate of acetylsalicylic acid is extremely variable, depending on several factors ⁶. Dosage adjustments may be required in patients with renal impairment ^Label. The extended-release tablet should not be administered to patients with eGFR of less than 10 mL/min ²².

Adverse Effects

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Toxicity

Lethal doses

Acute oral LD50 values have been reported as over 1.0 g/kg in humans, cats, and dogs, 0.92 g/kg - 1.48 g/kg in albino rats, 1.19 g/kg in guinea pigs, 1.1 g/kg in mice, and 1.8 g/kg in rabbit models ^Label.

Acute toxicity

Salicylate toxicity is a problem that may develop with both acute and chronic salicylate exposure ⁷. Multiple organ systems may be affected by salicylate toxicity, including the central nervous system, the pulmonary system, and the gastrointestinal system. Severe bleeding may occur. In the majority of cases, patients suffering from salicylate toxicity are volume-depleted at the time of presentation for medical attention. Fluid resuscitation should occur immediately and volume status should be monitored closely. Disruptions in acid-base balance are frequent in ASA toxicity ⁷.

The acute toxicity of acetylsalicylic in animals has been widely studied. The signs of poisoning in rats from lethal doses are mild to severe gastroenteritis, hepatitis, nephritis, pulmonary edema, encephalopathy, shock and some toxic effects on other organs and tissues. Mortality has been observed following convulsions or cardiovascular shock. An important differentiating property between various animal species is the ability to vomit toxic doses. Humans, cats and dogs have this ability, but rodents or rabbits do not ^Label.

Chronic toxicity and carcinogenesis

Chronic ASA toxicity is frequently accompanied by atypical clinical presentations that may be similar to diabetic ketoacidosis, delirium, cerebrovascular accident (CVA), myocardial infarction (MI) or cardiac failure. Plasma salicylate concentrations should be measured if salicylate intoxication is suspected, even if there no documentation available to suggest ASA was ingested. In older age, nephrotoxicity from salicylates increases, and the risk of upper gastrointestinal hemorrhage is increased, with higher rates of mortality ⁸. It is also important to note that ASA toxicity may occur even with close to normal serum concentrations. Prevention of chronic ASA includes the administration of smallest possible doses, avoidance of concurrent use of salicylate drugs, and therapeutic drug monitoring. Renal function should be regularly monitored and screening for gastrointestinal bleeding should be done at regular intervals ⁸.

Chronic toxicity studies were performed in rodents. ASA was administered at doses measured to be 2 to 20 times the maximum tolerated clinical dose to mice for up to one year. Negative dose-related effects were seen. These include decreased mean survival time, decreased number of births and progeny reaching an appropriate age for weaning. No evidence of carcinogenesis was found in 1-year studies ^Label. At daily doses of 0.24 g/kg/day given for 100 days to albino rats, ASA led to signs to excessive thirst, aciduria, diuresis, drowsiness, hyperreflexia, piloerection, changes in respiration, tachycardia, followed by soft stools, epistaxis, sialorrhea, dacryorrhea and mortality during hypothermic coma in the second study month ^Label.

Use in pregnancy and lactation

While teratogenic effects were observed in animals nearly lethal doses, no evidence suggests that this drug is teratogenic in humans ^Label. It is advisable, however, to avoid ASA use the first and second trimester of pregnancy, unless it is clearly required. If acetylsalicylic acid containing drugs are ingested by a patient attempting to conceive, or during the first and second trimester of pregnancy, the lowest possible dose at the shortest possible duration should be taken ^Label. This drug is contraindicated in the 3rd trimester of pregnancy ^Label.

Pathways

Pathway	Category
Acetylsalicylic Acid Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Cytochrome P450 2C9	CYP2C9*3	(C;C) / (A;C)	C Allele	Effect Directly Studied	Patients with this genotype have reduced metabolism of acetylsalicylic acid.	Details
Leukotriene C4 synthase	---	(A;C) / (C;C)	C allele	ADR Directly Studied	The presence of this genotype in LTC4S may indicate an increased risk of chronic urticaria when treated with acetylsalicylic acid.	Details
Integrin beta-3	GPIIIa PlA2	(C;C) / (C;T)	T > C	Effect Directly Studied	Patients with this genotype have increased resistance to the anti-thrombotic effects of aspirin.	Details
Cytochrome P450 2C9	CYP2C9*6	Not Available	818delA	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*15	Not Available	485C>A	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*25	Not Available	353_362delAGAAATGGAA	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*35	Not Available	374G>T / 430C>T	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*2	Not Available	430C>T	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*4	Not Available	1076T>C	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*5	Not Available	1080C>G	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*8	Not Available	449G>A	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*11	Not Available	1003C>T	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*12	Not Available	1465C>T	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*13	Not Available	269T>C	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*14	Not Available	374G>A	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*16	Not Available	895A>G	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*18	Not Available	1075A>C / 1190A>C … show all	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*26	Not Available	389C>G	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*28	Not Available	641A>T	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*30	Not Available	1429G>A	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2C9	CYP2C9*33	Not Available	395G>A	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Acetylsalicylic acid may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abatacept	The metabolism of Acetylsalicylic acid can be increased when combined with Abatacept.
Abciximab	Acetylsalicylic acid may increase the antiplatelet activities of Abciximab.
Abrocitinib	The risk or severity of bleeding and thrombocytopenia can be increased when Acetylsalicylic acid is combined with Abrocitinib.
Acamprosate	The excretion of Acamprosate can be decreased when combined with Acetylsalicylic acid.

Food Interactions

Avoid alcohol. Alcohol increases the risk of gastrointestinal bleeding.
Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
Take after a meal. This reduces irritating gastrointestinal effects.
Take with a full glass of water.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Lysine acetylsalicylate	2JJ274J145	62952-06-1	JJBCTCGUOQYZHK-UHFFFAOYSA-N

Product Images

International/Other Brands

Acenterine / Acetophen (Merck) / Adiro / Aspergum / Aspro / Easprin / Empirin / Nu-seals / Rhodine / Rhonal / Solprin / Solprin acid / St. Joseph Aspirin for Adults / Tasprin

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Durlaza	Capsule, extended release	162.5 mg/1	Oral	New Haven Pharmaceuticals, Inc.	2015-09-25	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
365 Everyday Value Aspirin	Tablet, film coated	325 mg/1	Oral	Whole Foods Market, Inc.	2018-08-23	Not applicable
365 Everyday Value Aspirin	Tablet, film coated	325 mg/1	Oral	Whole Foods Market, Inc.	2021-06-08	Not applicable
7 Select Adult Chewable Aspirin	Tablet, chewable	81 mg/1	Oral	7 Eleven	2014-08-05	2017-08-09
7 Select Aspirin	Tablet, film coated	325 mg/1	Oral	7-Eleven	2014-08-05	2021-03-31
81 mg Low Dose Aspirin	Tablet	81 mg/1	Oral	Big Lots Stores, Inc.	2008-02-12	2013-06-25

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
10 Person ANSI	Acetylsalicylic acid (325 mg/1) + Acetaminophen (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ibuprofen (200 mg/1) + Lidocaine (0.5 1/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Topical	Genuine First Aid	2010-04-24	Not applicable
217	Acetylsalicylic acid (325 mg / tab) + Caffeine citrate (30 mg / tab)	Tablet	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1910-12-31	1998-04-21
217 Strong Tab	Acetylsalicylic acid (500 mg / tab) + Caffeine citrate (30 mg / tab)	Tablet	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1973-12-31	1998-04-21
222 Tablets	Acetylsalicylic acid (375 mg) + Caffeine citrate (30 mg) + Codeine phosphate (8 mg)	Tablet	Oral	Mcneil Consumer Healthcare Division Of Johnson & Johnson Inc	1951-12-31	2015-08-17
25 Person ANSI	Acetylsalicylic acid (325 mg/1) + Acetaminophen (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ethanol (62 g/100g) + Ibuprofen (200 mg/1) + Isopropyl alcohol (70 mL/100mL) + Lidocaine (0.5 g/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Topical	Genuine First Aid	2010-04-25	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
4032 First Aid Kit	Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Inhalant; Kit; Liquid; Ointment; Spray; Tablet	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4134 First Aid Kit	Acetylsalicylic acid (325 mg/1) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Water (98.6 mL/100mL)	Cream; Kit; Liquid; Tablet	Ophthalmic; Oral; Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4139 First Aid Kit	Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g)	Kit	Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4142 First Aid Kit	Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Lidocaine hydrochloride (2 g/100g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4154 First Aid Kit	Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g)	Kit	Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable

Chemical Identifiers

UNII: R16CO5Y76E
CAS number: 50-78-2
InChI Key: BSYNRYMUTXBXSQ-UHFFFAOYSA-N
InChI: InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
IUPAC Name: 2-(acetyloxy)benzoic acid
SMILES: CC(=O)OC1=CC=CC=C1C(O)=O

References

Synthesis Reference

Marino Gobetti, Guido Vandoni, "Acetylsalicylic acid thioesters, a process for their preparation and pharmaceutical compositions containing them." U.S. Patent US4563443, issued March, 1981.

US4563443

General References

Macdonald S: Aspirin use to be banned in under 16 year olds. BMJ. 2002 Nov 2;325(7371):988. [Article]
Sneader W: The discovery of aspirin: a reappraisal. BMJ. 2000 Dec 23-30;321(7276):1591-4. [Article]
Aukerman G, Knutson D, Miser WF: Management of the acute migraine headache. Am Fam Physician. 2002 Dec 1;66(11):2123-30. [Article]
Authors unspecified: Randomised trial of intravenous streptokinase, oral aspirin, both, or neither among 17,187 cases of suspected acute myocardial infarction: ISIS-2. ISIS-2 (Second International Study of Infarct Survival) Collaborative Group. Lancet. 1988 Aug 13;2(8607):349-60. [Article]
Dorsch MP, Lee JS, Lynch DR, Dunn SP, Rodgers JE, Schwartz T, Colby E, Montague D, Smyth SS: Aspirin resistance in patients with stable coronary artery disease with and without a history of myocardial infarction. Ann Pharmacother. 2007 May;41(5):737-41. Epub 2007 Apr 24. [Article]
Levy G: Clinical pharmacokinetics of aspirin. Pediatrics. 1978 Nov;62(5 Pt 2 Suppl):867-72. [Article]
Authors unspecified: Guidance document: management priorities in salicylate toxicity. J Med Toxicol. 2015 Mar;11(1):149-52. doi: 10.1007/s13181-013-0362-3. [Article]
Durnas C, Cusack BJ: Salicylate intoxication in the elderly. Recognition and recommendations on how to prevent it. Drugs Aging. 1992 Jan-Feb;2(1):20-34. [Article]
Flower R: What are all the things that aspirin does? BMJ. 2003 Sep 13;327(7415):572-3. doi: 10.1136/bmj.327.7415.572. [Article]
Hall MN, Campos H, Li H, Sesso HD, Stampfer MJ, Willett WC, Ma J: Blood levels of long-chain polyunsaturated fatty acids, aspirin, and the risk of colorectal cancer. Cancer Epidemiol Biomarkers Prev. 2007 Feb;16(2):314-21. [Article]
Vane JR, Botting RM: The mechanism of action of aspirin. Thromb Res. 2003 Jun 15;110(5-6):255-8. [Article]
Vane JR, Bakhle YS, Botting RM: Cyclooxygenases 1 and 2. Annu Rev Pharmacol Toxicol. 1998;38:97-120. doi: 10.1146/annurev.pharmtox.38.1.97. [Article]
Varga Z, Sabzwari SRA, Vargova V: Cardiovascular Risk of Nonsteroidal Anti-Inflammatory Drugs: An Under-Recognized Public Health Issue. Cureus. 2017 Apr 8;9(4):e1144. doi: 10.7759/cureus.1144. [Article]
Ornelas A, Zacharias-Millward N, Menter DG, Davis JS, Lichtenberger L, Hawke D, Hawk E, Vilar E, Bhattacharya P, Millward S: Beyond COX-1: the effects of aspirin on platelet biology and potential mechanisms of chemoprevention. Cancer Metastasis Rev. 2017 Jun;36(2):289-303. doi: 10.1007/s10555-017-9675-z. [Article]
Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [Article]
Tsoi KKF, Ho JMW, Chan FCH, Sung JJY: Long-term use of low-dose aspirin for cancer prevention: A 10-year population cohort study in Hong Kong. Int J Cancer. 2018 Dec 21. doi: 10.1002/ijc.32083. [Article]
Li D, Wang P, Yu Y, Huang B, Zhang X, Xu C, Zhao X, Yin Z, He Z, Jin M, Liu C: Tumor-preventing activity of aspirin in multiple cancers based on bioinformatic analyses. PeerJ. 2018 Sep 26;6:e5667. doi: 10.7717/peerj.5667. eCollection 2018. [Article]
Hasan Arif; Sandeep Aggarwal (2018). Salicylic Acid (Aspirin): StatPearls. StatPearls Publishing.
Mayo Clinic website: Salicylate [Link]
Health Canada Product Monograph: Aspirin (acetylsalicylic acid) for oral administration [Link]
FDA Approved Drug Products: SYNALGOS®-DC (aspirin, caffeine, and dihydrocodeine bitartrate) capsules, for oral use, CIII (Jan 2024) [Link]
Durlaza FDA label [File]

External Links

Human Metabolome Database: HMDB0001879
KEGG Drug: D00109
KEGG Compound: C01405
PubChem Compound: 2244
PubChem Substance: 46505803
ChemSpider: 2157
BindingDB: 22360
RxNav: 1191
ChEBI: 15365
ChEMBL: CHEMBL25
ZINC: ZINC000000000053
Therapeutic Targets Database: DAP000843
PharmGKB: PA448497
Guide to Pharmacology: GtP Drug Page
PDBe Ligand: AIN
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Aspirin

PDB Entries

1oxr / 1tgm / 2qqt / 3gcl / 3iaz / 4nsb / 6mqf / 8j3w

FDA label

Download (399 KB)

MSDS

Download (24.2 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Atrial Fibrillation / Stroke	1
4	Active Not Recruiting	Prevention	Cancer	1
4	Active Not Recruiting	Prevention	Diabetes Mellitus	1
4	Active Not Recruiting	Treatment	Acute Coronary Syndrome (ACS)	1
4	Active Not Recruiting	Treatment	Acute Coronary Syndrome (ACS) / Coronary Artery Disease (CAD) / Diabetes Mellitus / Obesity	1

Pharmacoeconomics

Manufacturers

Bayer healthcare llc

Packagers

A-S Medication Solutions LLC
BASF Corp.
Excellium Pharmaceutical Inc.
Harvest Pharmaceuticals Inc.
Kaiser Foundation Hospital
Major Pharmaceuticals
Mckesson Corp.
Par Pharmaceuticals
Prepak Systems Inc.
Rosedale Therapeutics
Time-Cap Labs
United Research Laboratories Inc.

Dosage Forms

Form	Route	Strength
Tablet	Oral
Inhalant; kit; liquid; ointment; spray; tablet	Ophthalmic; Oral; Respiratory (inhalation); Topical
Cream; kit; liquid; tablet	Ophthalmic; Oral; Topical
Cream; kit; liquid; ointment; swab; tablet	Ophthalmic; Oral; Topical
Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical
Inhalant; kit; liquid; spray; tablet	Ophthalmic; Oral; Respiratory (inhalation); Topical
Cream; inhalant; kit; swab; tablet	Oral; Respiratory (inhalation); Topical
Kit	Oral; Respiratory (inhalation); Topical
Inhalant; kit; liquid; ointment; spray; swab; tablet	Ophthalmic; Oral; Respiratory (inhalation); Topical
Cream; kit; liquid; ointment; spray; tablet	Ophthalmic; Oral; Topical
Cream; kit; liquid; ointment; swab; tablet	Oral; Topical
Kit; liquid; ointment; swab; tablet	Ophthalmic; Oral; Topical
Kit; liquid; ointment; swab; tablet	Oral; Topical
Kit; liquid; ointment; spray; tablet	Ophthalmic; Oral; Topical
Kit	Irrigation; Oral; Respiratory (inhalation); Topical
Kit	Irrigation; Ophthalmic; Oral; Respiratory (inhalation); Topical
Tablet	Oral	250 MG
Injection, powder, for solution	Intramuscular; Intravenous	1000 mg
Injection, powder, for solution	Intramuscular; Intravenous	500 mg
Injection, powder, for solution	Intravenous; Parenteral	1 g/5ml
Injection, powder, for solution	Intravenous; Parenteral	500 mg/2.5ml
Powder, for solution	Oral	1000 mg
Powder, for solution	Oral	200 mg
Powder, for solution	Oral	500 mg
Suppository	Rectal	0.6 g
Suppository	Rectal	1.3 g
Suppository	Rectal	1300 mg
Suppository	Rectal	600 mg
Tablet; tablet, film coated	Oral
Tablet	Oral	325 mg / tab
Injection, powder, for solution
Powder, for solution	Oral
Granule, effervescent	Oral	9.88 g
Kit; tablet, delayed release; tablet, extended release	Oral
Tablet, delayed release	Oral	81 mg/1
Tablet	Oral	325 1/1
Kit	Oral; Topical
Kit	Topical
Capsule	Oral	25.000 MG
Capsule, extended release	Oral
Tablet, effervescent	Oral	324 mg
Granule, effervescent	Oral
Tablet, effervescent	Oral	325 mg/1
Tablet, effervescent	Oral
Tablet	Oral	324 mg
Capsule	Oral	125 MG
Capsule	Oral	500 MG
Capsule, coated pellets		160 mg
Tablet	Oral	300.00 mg
Tablet, delayed release	Oral	975 mg / tab
Tablet, delayed release	Oral	600 mg / tab
Tablet, delayed release	Oral	650 mg / tab
Suppository	Rectal	150 mg
Suppository	Rectal	650 mg
Capsule, extended release	Oral
Tablet, chewable	Oral	80 mg
Tablet, delayed release	Oral	162 mg
Capsule, delayed release	Oral
Tablet, film coated	Oral	500 mg/1
Tablet	Oral	300 mg
Tablet, delayed release	Oral	81 mg
Gum, chewing	Oral	325 mg / gum
Tablet, film coated	Oral
Suppository	Rectal	300 mg/1
Suppository	Rectal	600 mg/1
Tablet	Oral	325 g/1
Tablet	Oral	325 mg/1
Tablet, coated	Oral	325 ng/1
Tablet, coated	Oral	325 mg/1
Tablet, extended release	Oral	81 mg/1
Tablet, film coated	Oral	325 mg/1
Tablet	Oral	80 mg / tab
Tablet, coated	Oral	100 mg
Tablet	Oral
Tablet, coated	Oral	500 MG
Tablet, delayed release; tablet, extended release	Oral	325 mg / tab
Tablet, delayed release; tablet, extended release	Oral	500 mg / tab
Tablet, delayed release	Oral	81 mg/811
Tablet, chewable	Oral	500 mg
Granule	Oral	500 mg
Tablet, coated	Oral	81 mg/1
Tablet, delayed release	Oral	325 mg / ect
Granule	Oral	500 mg / pck
Tablet, coated	Oral	500 mg/5001
Tablet	Oral	500 mg / tab
Granule	Oral	500 mg / sachet
Tablet	Oral	81 mg/1
Tablet, film coated	Oral	81 mg/1
Tablet, chewable	Oral	81 mg/1
Tablet, film coated	Oral	100 mg
Powder	Oral	325 mg/1
Granule	Oral
Suppository	Rectal	1 G
Suppository	Rectal	300 mg
Tablet	Oral	100 MG
Tablet	Oral	500.000 mg
Tablet, effervescent	Oral	400 MG
Tablet, effervescent	Oral	400 MG
Pill
Granule, effervescent	Oral	500 mg
Granule	Oral	500.00 mg
Granule, for suspension	Oral	30 MG
Tablet, effervescent	Oral	500 mg
Tablet, coated	Oral
Capsule	Oral
Tablet, effervescent	Oral
Tablet	Oral	320 mg
Tablet, delayed release	Oral	75 MG
Tablet, film coated	Oral	30 mg
Tablet	Oral	75 MG
Granule, for suspension	Oral
Tablet, delayed release	Oral	325 mg / tab
Capsule
Aerosol, metered; injection; kit; tablet; tablet, chewable	Intramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual
Tablet	Oral	500 mg/1
Powder	Oral	500 mg/1
Tablet, coated	Oral	500 mg/1
Spray	Oral	6 mg/0.1mL
Lozenge	Oral
Capsule	Oral	100.00 mg
Capsule	Oral
Tablet, orally disintegrating	Oral
Capsule, coated	Oral	100 mg
Tablet	Oral	0.5 G
Tablet	Oral	324 MG
Tablet, delayed release	Oral	10000000 mg
Powder, for solution	Oral	100 MG
Powder, for solution	Oral	160 MG
Powder, for solution	Oral	300 MG
Powder, for solution	Oral	75 MG
Suppository	Rectal
Tablet, delayed release	Oral	80 mg / tab
Tablet, chewable	Oral
Tablet, film coated	Oral	100 mg
Granule	Oral	300.000 mg
Tablet	Oral	100.000 mg
Aerosol, metered; injection; kit; solution; tablet; tablet, chewable	Intramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual
Tablet	Oral	300.000 mg
Paste	Dental
Capsule, extended release	Oral	162.5 mg/1
Tablet, coated	Oral	150 mg
Tablet, delayed release	Oral	150 mg
Capsule, coated	Oral	324 mg
Capsule, coated	Oral	150 mg
Capsule, coated	Oral	300 mg
Capsule, coated	Oral	500 mg
Tablet, delayed release	Oral	325 mg/3251
Tablet, delayed release	Oral	325 mg
Tablet, delayed release	Oral	650 mg
Tablet, chewable	Oral	81 mg
Tablet, delayed release	Oral	500 mg
Tablet, delayed release	Oral	975 mg
Tablet, chewable	Oral	325 mg
Kit; tablet, film coated	Oral
Capsule, gelatin coated	Oral
Tablet, delayed release	Oral	100 MG
Tablet, orally disintegrating	Oral	81 mg/1
Tablet	Oral	50 MG
Kit	Ophthalmic; Oral; Topical
Capsule, coated	Oral
Tablet, coated	Oral	162 mg/1621
Tablet, coated	Oral	81 mg/811
Tablet, film coated	Topical
Powder	Oral
Tablet	Oral	300 mg / tab
Tablet, delayed release	Oral	50 mg
Tablet	Oral	500.00 mg
Tablet	Oral	100.00 mg
Capsule	Oral	10.400 mg
Tablet, coated	Oral
Kit	Oral	325 mg/1
Tablet, chewable	Buccal	500 mg
Tablet, delayed release	Oral
Tablet	Oral	450 mg
Tablet, multilayer	Oral
Tablet, film coated	Oral
Kit; tablet; tablet, delayed release	Oral
Tablet	Oral	81 mg
Tablet, delayed release	Oral	80 mg
Tablet	Oral	100.0 mg
Kit	Oral
Tablet
Tablet	Oral	300.000 mg
Tablet, delayed release	Oral	325 mg/1
Tablet	Oral	80 mg
Strip	Oral	81 mg/1
Powder	Oral	600 mg
Powder	Oral
Tablet, film coated	Oral	50 mg
Tablet, film coated	Oral	75 mg
Tablet, delayed release	Oral
Tablet, soluble	Oral	300 mg
Tablet	Oral	81 mg/81mg
Tablet	Oral	325 mg/325mg
Capsule	Oral	325 mg/325mg
Capsule	Oral	81 mg/81mg
Tablet, effervescent	Oral	350 mg
Tablet, delayed release	Oral	60 mg
Powder	Oral	650 mg/1sachet
Powder, for solution	Oral	162 mg/1sachet
Powder	Oral	162 mg/1sachet
Tablet	Oral	325 mg
Tablet	Oral	162 mg
Tablet	Oral	500 mg
Tablet, film coated	Oral	300 mg
Tablet, film coated	Oral	500 mg
Tablet, delayed release	Oral	300 mg

Prices

Unit description	Cost	Unit
Entrophen 10 650 mg Enteric-Coated Tablet	0.09USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5972916	No	1999-10-26	2017-07-14
US6015577	No	2000-01-18	2017-01-18
US6926907	No	2005-08-09	2023-02-28
US9101637	No	2015-08-11	2022-03-23
US9226892	No	2016-01-05	2032-09-29
US8865187	No	2014-10-21	2022-03-23
US9216150	No	2015-12-22	2032-09-29
US9351984	No	2016-05-31	2021-12-19
US9539214	No	2017-01-10	2033-03-13
US9364439	No	2016-06-14	2022-05-31
US8206741	No	2012-06-26	2023-02-28
US9987231	No	2018-06-05	2033-01-02
US10786444	No	2020-09-29	2032-09-29
US10646431	No	2020-05-12	2032-09-29

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	138-140	http://www.rsc.org/learn-chemistry/content/filerepository/CMP/00/000/045/Aspirin.pdf
boiling point (°C)	140 °C	http://www.chemicalland21.com/lifescience/phar/ACETYLSALICYLIC%20ACID.htm
water solubility	10 mg/mL	https://www.sigmaaldrich.com/catalog/product/sigma/a5376?lang=en®ion=US
logP	1.18	https://www.fip.org/files/fip/BPS/BCS/Monographs/AcetylsalicylicAcid.pdf
pKa	3.5	https://www.fip.org/files/fip/BPS/BCS/Monographs/AcetylsalicylicAcid.pdf

Predicted Properties

Property	Value	Source
logP	1.24	Chemaxon
pKa (Strongest Acidic)	3.41	Chemaxon
pKa (Strongest Basic)	-7.1	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	63.6 Å²	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	44.45 m³·mol^-1	Chemaxon
Polarizability	17.1 Å³	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9645
Blood Brain Barrier	+	0.9376
Caco-2 permeable	-	0.6607
P-glycoprotein substrate	Non-substrate	0.685
P-glycoprotein inhibitor I	Non-inhibitor	0.9118
P-glycoprotein inhibitor II	Non-inhibitor	0.9615
Renal organic cation transporter	Non-inhibitor	0.914
CYP450 2C9 substrate	Non-substrate	0.7518
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.7225
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9576
CYP450 2C19 inhibitor	Non-inhibitor	0.9445
CYP450 3A4 inhibitor	Non-inhibitor	0.9611
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9557
Ames test	Non AMES toxic	0.9326
Carcinogenicity	Non-carcinogens	0.8356
Biodegradation	Ready biodegradable	0.9067
Rat acute toxicity	2.6386 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9433
hERG inhibition (predictor II)	Non-inhibitor	0.9799

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (8.27 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	GC-MS	splash10-014l-2960000000-ffcb8d28ab7e460b0da8
GC-MS Spectrum - GC-MS (1 TMS)	GC-MS	splash10-006w-2910000000-910e8ce2493a05870b33
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-000f-8900000000-760033c820b78b9452ed
GC-MS Spectrum - EI-B	GC-MS	splash10-00dl-9400000000-64327d3bef0063cf4fe1
GC-MS Spectrum - CI-B	GC-MS	splash10-00di-0900000000-113943b65024522c1712
GC-MS Spectrum - EI-B	GC-MS	splash10-014i-1590000000-7890c99ca2b0e2c4ff19
GC-MS Spectrum - GC-EI-TOF	GC-MS	splash10-014l-2960000000-ffcb8d28ab7e460b0da8
GC-MS Spectrum - GC-MS	GC-MS	splash10-006w-2910000000-910e8ce2493a05870b33
GC-MS Spectrum - GC-EI-TOF	GC-MS	splash10-006w-2900000000-253eb678a85f77d4ba61
Mass Spectrum (Electron Ionization)	MS	splash10-00dl-6900000000-74f8a29aa18d0c3afe98
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	LC-MS/MS	splash10-00kr-6900000000-324f46e8def1652ed4bf
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	LC-MS/MS	splash10-000i-9000000000-cdf64eaf75083da6f355
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	LC-MS/MS	splash10-000i-9000000000-ee75806b6fb8a38fd697
MS/MS Spectrum - EI-B (Unknown) , Positive	LC-MS/MS	splash10-00dl-9400000000-64327d3bef0063cf4fe1
MS/MS Spectrum - CI-B (Unknown) , Positive	LC-MS/MS	splash10-00di-0900000000-113943b65024522c1712
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-000i-1900000000-bc50013edb10656e0aa4
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-000i-2900000000-8c55c1f8d7cb7f247a5d
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-000l-9700000000-d475fd0478daf18a419a
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0006-9100000000-3daaf3c8697e17e67869
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0006-9000000000-ee876bcdd1a5c7c229a0
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0006-9000000000-cd4e1f8fe0a2bbc869f9
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0006-9000000000-4dca49851b5b9fd03d1a
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-00kf-9000000000-4611655c6aff89d706eb
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-014l-9000000000-4d636e2d7318b857528d
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01ot-0900000000-1256ca04e4244fbc4a64
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01ot-0900000000-2cae7e19320bfa1a03a0
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01ot-0900000000-42f69c49b256900b7524
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01ot-0900000000-4860d5cbeeb9c31311ec
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-006t-3900000000-cc185048e2a1bcc52124
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01ba-9700000000-ec436cb71e803899f611
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-014i-9100000000-75f611f9e761b63033d9
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-02tc-9000000000-15b9abe0f191aedd9620
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0ik9-9000000000-644d508a79eb48c24ec3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00di-2900000000-2ab828a7536781de1619
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000f-9500000000-011bc0f7039840e7abc0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-9400000000-19a4db7d336956a3f80c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00di-1900000000-a6b55a2f37579bbedabb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-9000000000-9b2b9c5199bdf878e508
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0htc-9300000000-d6619670e0a60acb8ccb
1H NMR Spectrum	1D NMR	Not Applicable
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	141.5303277	predicted	DarkChem Lite v0.1.0
[M-H]-	142.4774277	predicted	DarkChem Lite v0.1.0
[M-H]-	142.6834277	predicted	DarkChem Lite v0.1.0
[M-H]-	142.6346277	predicted	DarkChem Lite v0.1.0
[M-H]-	131.71933	predicted	DeepCCS 1.0 (2019)
[M+H]+	141.1519277	predicted	DarkChem Lite v0.1.0
[M+H]+	144.2585277	predicted	DarkChem Lite v0.1.0
[M+H]+	143.5771277	predicted	DarkChem Lite v0.1.0
[M+H]+	143.6946277	predicted	DarkChem Lite v0.1.0
[M+H]+	135.44505	predicted	DeepCCS 1.0 (2019)
[M+Na]+	142.0109277	predicted	DarkChem Lite v0.1.0
[M+Na]+	142.5911277	predicted	DarkChem Lite v0.1.0
[M+Na]+	142.6670277	predicted	DarkChem Lite v0.1.0
[M+Na]+	142.7571277	predicted	DarkChem Lite v0.1.0
[M+Na]+	144.68927	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	100000	N/A	N/A	A27766
IC 50 (nM)	750410	N/A	N/A	A27769
IC 50 (nM)	560100	N/A	N/A	A29232

Details1. Prostaglandin G/H synthase 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Prostaglandin-endoperoxide synthase activity
Specific Function: Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name: PTGS1
Uniprot ID: P23219
Uniprot Name: Prostaglandin G/H synthase 1
Molecular Weight: 68685.82 Da

References

Flipo RM: [Are the NSAIDs able to compromising the cardio-preventive efficacy of aspirin?]. Presse Med. 2006 Sep;35(9 Spec No 1):1S53-60. [Article]
Schwartz KA: Aspirin resistance: a review of diagnostic methodology, mechanisms, and clinical utility. Adv Clin Chem. 2006;42:81-110. [Article]
Birnbaum Y, Ye Y, Lin Y, Freeberg SY, Huang MH, Perez-Polo JR, Uretsky BF: Aspirin augments 15-epi-lipoxin A4 production by lipopolysaccharide, but blocks the pioglitazone and atorvastatin induction of 15-epi-lipoxin A4 in the rat heart. Prostaglandins Other Lipid Mediat. 2007 Feb;83(1-2):89-98. Epub 2006 Nov 7. [Article]
Guthikonda S, Lev EI, Patel R, DeLao T, Bergeron AL, Dong JF, Kleiman NS: Reticulated platelets and uninhibited COX-1 and COX-2 decrease the antiplatelet effects of aspirin. J Thromb Haemost. 2007 Mar;5(3):490-6. [Article]
Durlaza FDA label [File]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	18000000	N/A	N/A	A27774
IC 50 (nM)	62500	N/A	N/A	A29233
IC 50 (nM)	1050000	N/A	N/A	A29234
IC 50 (nM)	2400	8	37	A28387
IC 50 (nM)	19800	N/A	N/A	A29235
IC 50 (nM)	100000	N/A	N/A	A28389
IC 50 (nM)	710000	N/A	N/A	A27766
IC 50 (nM)	2400	N/A	N/A	A28402 / A29236 / A28406 / A28407 / A27813 / A27814 / A28423
IC 50 (nM)	1000000	N/A	N/A	A27769
IC 50 (nM)	1413300	N/A	N/A	A29232
Ki (nM)	>10000	N/A	N/A	A5629 / A27471
Ki (nM)	7500	N/A	N/A	A27471

Details2. Prostaglandin G/H synthase 2

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Prostaglandin-endoperoxide synthase activity
Specific Function: Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name: PTGS2
Uniprot ID: P35354
Uniprot Name: Prostaglandin G/H synthase 2
Molecular Weight: 68995.625 Da

References

Hall MN, Campos H, Li H, Sesso HD, Stampfer MJ, Willett WC, Ma J: Blood levels of long-chain polyunsaturated fatty acids, aspirin, and the risk of colorectal cancer. Cancer Epidemiol Biomarkers Prev. 2007 Feb;16(2):314-21. [Article]
Vane JR, Botting RM: The mechanism of action of aspirin. Thromb Res. 2003 Jun 15;110(5-6):255-8. [Article]

Details3. Aldo-keto reductase family 1 member C1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: This is a potential target. Supporting data in the literature are limited.

General Function: Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function: Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the in...
Gene Name: AKR1C1
Uniprot ID: Q04828
Uniprot Name: Aldo-keto reductase family 1 member C1
Molecular Weight: 36788.02 Da

References

Dhagat U, Carbone V, Chung RP, Matsunaga T, Endo S, Hara A, El-Kabbani O: A salicylic acid-based analogue discovered from virtual screening as a potent inhibitor of human 20alpha-hydroxysteroid dehydrogenase. Med Chem. 2007 Nov;3(6):546-50. [Article]

Details4. 5'-AMP-activated protein kinase (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Activator

General Function: Tau-protein kinase activity
Specific Function: Catalytic subunit of AMP-activated protein kinase (AMPK), an energy sensor protein kinase that plays a key role in regulating cellular energy metabolism. In response to reduction of intracellular A...

Components:

Name	UniProt ID
5'-AMP-activated protein kinase catalytic subunit alpha-1	Q13131
5'-AMP-activated protein kinase catalytic subunit alpha-2	P54646
5'-AMP-activated protein kinase subunit beta-1	Q9Y478
5'-AMP-activated protein kinase subunit beta-2	O43741
5'-AMP-activated protein kinase subunit gamma-1	P54619
5'-AMP-activated protein kinase subunit gamma-2	Q9UGJ0
5'-AMP-activated protein kinase subunit gamma-3	Q9UGI9

References

Din FV, Valanciute A, Houde VP, Zibrova D, Green KA, Sakamoto K, Alessi DR, Dunlop MG: Aspirin inhibits mTOR signaling, activates AMP-activated protein kinase, and induces autophagy in colorectal cancer cells. Gastroenterology. 2012 Jun;142(7):1504-15.e3. doi: 10.1053/j.gastro.2012.02.050. Epub 2012 Mar 6. [Article]
Hawley SA, Fullerton MD, Ross FA, Schertzer JD, Chevtzoff C, Walker KJ, Peggie MW, Zibrova D, Green KA, Mustard KJ, Kemp BE, Sakamoto K, Steinberg GR, Hardie DG: The ancient drug salicylate directly activates AMP-activated protein kinase. Science. 2012 May 18;336(6083):918-22. doi: 10.1126/science.1215327. Epub 2012 Apr 19. [Article]
Steinberg GR, Dandapani M, Hardie DG: AMPK: mediating the metabolic effects of salicylate-based drugs? Trends Endocrinol Metab. 2013 Oct;24(10):481-7. doi: 10.1016/j.tem.2013.06.002. Epub 2013 Jul 19. [Article]

Details5. Endothelin-1 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Phosphatidylinositol phospholipase c activity
Specific Function: Receptor for endothelin-1. Mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of binding affinities for ET-A is:...
Gene Name: EDNRA
Uniprot ID: P25101
Uniprot Name: Endothelin-1 receptor
Molecular Weight: 48721.76 Da

References

Talbodec A, Berkane N, Blandin V, Breittmayer JP, Ferrari E, Frelin C, Vigne P: Aspirin and sodium salicylate inhibit endothelin ETA receptors by an allosteric type of mechanism. Mol Pharmacol. 2000 Apr;57(4):797-804. [Article]
Blandin V, Vigne P, Breittmayer JP, Frelin C: Allosteric inhibition of endothelin ETA receptors by 3, 5-dibromosalicylic acid. Mol Pharmacol. 2000 Dec;58(6):1461-9. [Article]
Davenport AP, Hyndman KA, Dhaun N, Southan C, Kohan DE, Pollock JS, Pollock DM, Webb DJ, Maguire JJ: Endothelin. Pharmacol Rev. 2016 Apr;68(2):357-418. doi: 10.1124/pr.115.011833. [Article]

Details6. Cellular tumor antigen p53

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Not Available
Specific Function: Not Available
Gene Name: TP53
Uniprot ID: P04637
Uniprot Name: Cellular tumor antigen p53
Molecular Weight: 43652.79 Da

References

Alfonso LF, Srivenugopal KS, Bhat GJ: Does aspirin acetylate multiple cellular proteins? (Review). Mol Med Rep. 2009 Jul-Aug;2(4):533-7. doi: 10.3892/mmr_00000132. [Article]
Ai G, Dachineni R, Kumar DR, Marimuthu S, Alfonso LF, Bhat GJ: Aspirin acetylates wild type and mutant p53 in colon cancer cells: identification of aspirin acetylated sites on recombinant p53. Tumour Biol. 2016 May;37(5):6007-16. doi: 10.1007/s13277-015-4438-3. Epub 2015 Nov 23. [Article]
Su YF, Yang SH, Lee YH, Wu BC, Huang SC, Liu CM, Chen SL, Pan YF, Chou SS, Chou MY, Yang HW: Aspirin-induced inhibition of adipogenesis was p53-dependent and associated with inactivation of pentose phosphate pathway. Eur J Pharmacol. 2014 Sep 5;738:101-10. doi: 10.1016/j.ejphar.2014.03.009. Epub 2014 Apr 12. [Article]
Ranganathan S, Joseph J, Mehta JL: Aspirin inhibits human coronary artery endothelial cell proliferation by upregulation of p53. Biochem Biophys Res Commun. 2003 Jan 31;301(1):143-6. [Article]
Luciani MG, Campregher C, Gasche C: Aspirin blocks proliferation in colon cells by inducing a G1 arrest and apoptosis through activation of the checkpoint kinase ATM. Carcinogenesis. 2007 Oct;28(10):2207-17. doi: 10.1093/carcin/bgm101. Epub 2007 May 17. [Article]

Details7. 78 kDa glucose-regulated protein

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Binder
Curator comments: Data regarding this target in relation to acetylsalicylic acid are limited in the literature.

General Function: Unfolded protein binding
Specific Function: Probably plays a role in facilitating the assembly of multimeric protein complexes inside the endoplasmic reticulum. Involved in the correct folding of proteins and degradation of misfolded protein...
Gene Name: HSPA5
Uniprot ID: P11021
Uniprot Name: 78 kDa glucose-regulated protein
Molecular Weight: 72332.425 Da

References

Deng WG, Ruan KH, Du M, Saunders MA, Wu KK: Aspirin and salicylate bind to immunoglobulin heavy chain binding protein (BiP) and inhibit its ATPase activity in human fibroblasts. FASEB J. 2001 Nov;15(13):2463-70. [Article]

Details8. Ribosomal protein S6 kinase alpha-3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Ribosomal protein s6 kinase activity
Specific Function: Serine/threonine-protein kinase that acts downstream of ERK (MAPK1/ERK2 and MAPK3/ERK1) signaling and mediates mitogenic and stress-induced activation of the transcription factors CREB1, ETV1/ER81 ...
Gene Name: RPS6KA3
Uniprot ID: P51812
Uniprot Name: Ribosomal protein S6 kinase alpha-3
Molecular Weight: 83735.325 Da

References

Stevenson MA, Zhao MJ, Asea A, Coleman CN, Calderwood SK: Salicylic acid and aspirin inhibit the activity of RSK2 kinase and repress RSK2-dependent transcription of cyclic AMP response element binding protein- and NF-kappa B-responsive genes. J Immunol. 1999 Nov 15;163(10):5608-16. [Article]
Stratford AL, Dunn SE: The promise and challenges of targeting RSK for the treatment of cancer. Expert Opin Ther Targets. 2011 Jan;15(1):1-4. doi: 10.1517/14728222.2011.537656. [Article]
O'Neill EA: A new target for aspirin. Nature. 1998 Nov 5;396(6706):15, 17. doi: 10.1038/23810. [Article]

Details9. NF-kappa-B inhibitor alpha

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: Data in the literature are limited regarding this target action.

General Function: Ubiquitin protein ligase binding
Specific Function: Inhibits the activity of dimeric NF-kappa-B/REL complexes by trapping REL dimers in the cytoplasm through masking of their nuclear localization signals. On cellular stimulation by immune and proinf...
Gene Name: NFKBIA
Uniprot ID: P25963
Uniprot Name: NF-kappa-B inhibitor alpha
Molecular Weight: 35608.65 Da

References

Stevenson MA, Zhao MJ, Asea A, Coleman CN, Calderwood SK: Salicylic acid and aspirin inhibit the activity of RSK2 kinase and repress RSK2-dependent transcription of cyclic AMP response element binding protein- and NF-kappa B-responsive genes. J Immunol. 1999 Nov 15;163(10):5608-16. [Article]

Details10. Tumor necrosis factor-inducible gene 6 protein

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Downregulator

General Function: Hyaluronic acid binding
Specific Function: Possibly involved in cell-cell and cell-matrix interactions during inflammation and tumorigenesis.
Gene Name: TNFAIP6
Uniprot ID: P98066
Uniprot Name: Tumor necrosis factor-inducible gene 6 protein
Molecular Weight: 31203.09 Da

References

Shackelford RE, Alford PB, Xue Y, Thai SF, Adams DO, Pizzo S: Aspirin inhibits tumor necrosis factoralpha gene expression in murine tissue macrophages. Mol Pharmacol. 1997 Sep;52(3):421-9. [Article]
Jiang DQ, Liu H, Zhang SB, Zhang XL: Aspirin inhibits tumor necrosis factor-alpha-stimulated fractalkine expression in human umbilical vein endothelial cells. Chin Med J (Engl). 2009 May 20;122(10):1147-53. [Article]
Kim J, Lee KS, Kim JH, Lee DK, Park M, Choi S, Park W, Kim S, Choi YK, Hwang JY, Choe J, Won MH, Jeoung D, Lee H, Ryoo S, Ha KS, Kwon YG, Kim YM: Aspirin prevents TNF-alpha-induced endothelial cell dysfunction by regulating the NF-kappaB-dependent miR-155/eNOS pathway: Role of a miR-155/eNOS axis in preeclampsia. Free Radic Biol Med. 2017 Mar;104:185-198. doi: 10.1016/j.freeradbiomed.2017.01.010. Epub 2017 Jan 11. [Article]
Kutuk O, Basaga H: Aspirin inhibits TNFalpha- and IL-1-induced NF-kappaB activation and sensitizes HeLa cells to apoptosis. Cytokine. 2004 Mar 7;25(5):229-37. doi: 10.1016/j.cyto.2003.11.007. [Article]

Details11. Caspase-1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Downregulator

General Function: Endopeptidase activity
Specific Function: Thiol protease that cleaves IL-1 beta between an Asp and an Ala, releasing the mature cytokine which is involved in a variety of inflammatory processes. Important for defense against pathogens. Cle...
Gene Name: CASP1
Uniprot ID: P29466
Uniprot Name: Caspase-1
Molecular Weight: 45158.215 Da

References

Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [Article]
Pathi S, Jutooru I, Chadalapaka G, Nair V, Lee SO, Safe S: Aspirin inhibits colon cancer cell and tumor growth and downregulates specificity protein (Sp) transcription factors. PLoS One. 2012;7(10):e48208. doi: 10.1371/journal.pone.0048208. Epub 2012 Oct 26. [Article]
Zhang H, Lu J, Jiao Y, Chen Q, Li M, Wang Z, Yu Z, Huang X, Yao A, Gao Q, Xie W, Li L, Yao P: Aspirin Inhibits Natural Killer/T-Cell Lymphoma by Modulation of VEGF Expression and Mitochondrial Function. Front Oncol. 2019 Jan 14;8:679. doi: 10.3389/fonc.2018.00679. eCollection 2018. [Article]
Dhanoya T, Burn J: Colon cancer and Salicylates. Evol Med Public Health. 2016 Apr 15;2016(1):146-7. doi: 10.1093/emph/eow009. Print 2016. [Article]

Details12. Caspase-3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Downregulator

General Function: Phospholipase a2 activator activity
Specific Function: Involved in the activation cascade of caspases responsible for apoptosis execution. At the onset of apoptosis it proteolytically cleaves poly(ADP-ribose) polymerase (PARP) at a '216-Asp-|-Gly-217' ...
Gene Name: CASP3
Uniprot ID: P42574
Uniprot Name: Caspase-3
Molecular Weight: 31607.58 Da

References

Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [Article]
Pathi S, Jutooru I, Chadalapaka G, Nair V, Lee SO, Safe S: Aspirin inhibits colon cancer cell and tumor growth and downregulates specificity protein (Sp) transcription factors. PLoS One. 2012;7(10):e48208. doi: 10.1371/journal.pone.0048208. Epub 2012 Oct 26. [Article]

Details13. Inhibitor of nuclear factor kappa-B kinase subunit beta

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Scaffold protein binding
Specific Function: Serine kinase that plays an essential role in the NF-kappa-B signaling pathway which is activated by multiple stimuli such as inflammatory cytokines, bacterial or viral products, DNA damages or oth...
Gene Name: IKBKB
Uniprot ID: O14920
Uniprot Name: Inhibitor of nuclear factor kappa-B kinase subunit beta
Molecular Weight: 86563.245 Da

References

Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [Article]
Yamamoto Y, Yin MJ, Gaynor RB: IkappaB kinase alpha (IKKalpha) regulation of IKKbeta kinase activity. Mol Cell Biol. 2000 May;20(10):3655-66. [Article]
Konig HG, Watters O, Kinsella S, Ameen M, Fenner BJ, Prehn JHM: A constitutively-active IKK-complex at the axon initial segment. Brain Res. 2018 Jan 1;1678:356-366. doi: 10.1016/j.brainres.2017.10.020. Epub 2017 Oct 24. [Article]
Gamble C, McIntosh K, Scott R, Ho KH, Plevin R, Paul A: Inhibitory kappa B Kinases as targets for pharmacological regulation. Br J Pharmacol. 2012 Feb;165(4):802-19. doi: 10.1111/j.1476-5381.2011.01608.x. [Article]
Yamamoto Y, Gaynor RB: Therapeutic potential of inhibition of the NF-kappaB pathway in the treatment of inflammation and cancer. J Clin Invest. 2001 Jan;107(2):135-42. doi: 10.1172/JCI11914. [Article]
Rohl M, Pasparakis M, Baudler S, Baumgartl J, Gautam D, Huth M, De Lorenzi R, Krone W, Rajewsky K, Bruning JC: Conditional disruption of IkappaB kinase 2 fails to prevent obesity-induced insulin resistance. J Clin Invest. 2004 Feb;113(3):474-81. doi: 10.1172/JCI18712. [Article]

Details14. Extracellular signal-regulated kinase (ERK) (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown

General Function: Rna polymerase ii carboxy-terminal domain kinase activity
Specific Function: Serine/threonine kinase which acts as an essential component of the MAP kinase signal transduction pathway. MAPK1/ERK2 and MAPK3/ERK1 are the 2 MAPKs which play an important role in the MAPK/ERK ca...

Components:

Name	UniProt ID
Mitogen-activated protein kinase 1	P28482
Mitogen-activated protein kinase 15	Q8TD08
Mitogen-activated protein kinase 3	P27361
Mitogen-activated protein kinase 4	P31152
Mitogen-activated protein kinase 6	Q16659
Mitogen-activated protein kinase 7	Q13164

References

Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [Article]
Wang L, Wu J, Zhang W, Zhi Y, Wu Y, Jiang R, Yang R: Effects of aspirin on the ERK and PI3K/Akt signaling pathways in rats with acute pulmonary embolism. Mol Med Rep. 2013 Nov;8(5):1465-71. doi: 10.3892/mmr.2013.1676. Epub 2013 Sep 10. [Article]
Nishio T, Usami M, Awaji M, Shinohara S, Sato K: Dual effects of acetylsalicylic acid on ERK signaling and Mitf transcription lead to inhibition of melanogenesis. Mol Cell Biochem. 2016 Jan;412(1-2):101-10. doi: 10.1007/s11010-015-2613-x. Epub 2015 Dec 23. [Article]
Weissmann G, Montesinos MC, Pillinger M, Cronstein BN: Non-prostaglandin effects of aspirin III and salicylate: inhibition of integrin-dependent human neutrophil aggregation and inflammation in COX 2- and NF kappa B (P105)-knockout mice. Adv Exp Med Biol. 2002;507:571-7. [Article]

Details15. G1/S-specific cyclin-D1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Downregulator

General Function: Transcription factor binding
Specific Function: Regulatory component of the cyclin D1-CDK4 (DC) complex that phosphorylates and inhibits members of the retinoblastoma (RB) protein family including RB1 and regulates the cell-cycle during G(1)/S t...
Gene Name: CCND1
Uniprot ID: P24385
Uniprot Name: G1/S-specific cyclin-D1
Molecular Weight: 33728.74 Da

References

Law BK, Waltner-Law ME, Entingh AJ, Chytil A, Aakre ME, Norgaard P, Moses HL: Salicylate-induced growth arrest is associated with inhibition of p70s6k and down-regulation of c-myc, cyclin D1, cyclin A, and proliferating cell nuclear antigen. J Biol Chem. 2000 Dec 8;275(49):38261-7. doi: 10.1074/jbc.M005545200. [Article]
Cheng R, Liu YJ, Cui JW, Yang M, Liu XL, Li P, Wang Z, Zhu LZ, Lu SY, Zou L, Wu XQ, Li YX, Zhou Y, Fang ZY, Wei W: Aspirin regulation of c-myc and cyclinD1 proteins to overcome tamoxifen resistance in estrogen receptor-positive breast cancer cells. Oncotarget. 2017 May 2;8(18):30252-30264. doi: 10.18632/oncotarget.16325. [Article]
Fan W, Li J, Chen J, Zhu L, Wang Y, Sun B, Hua B, Guo C, Yan Z: Aspirin inhibits the proliferation of synovium-derived mesenchymal stem cells by arresting the cell cycle in the G0/G1 phase. Am J Transl Res. 2017 Nov 15;9(11):5056-5062. eCollection 2017. [Article]

Details16. Myc proto-oncogene protein

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Downregulator

General Function: Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function: Transcription factor that binds DNA in a non-specific manner, yet also specifically recognizes the core sequence 5'-CAC[GA]TG-3'. Activates the transcription of growth-related genes.
Gene Name: MYC
Uniprot ID: P01106
Uniprot Name: Myc proto-oncogene protein
Molecular Weight: 48803.55 Da

References

Law BK, Waltner-Law ME, Entingh AJ, Chytil A, Aakre ME, Norgaard P, Moses HL: Salicylate-induced growth arrest is associated with inhibition of p70s6k and down-regulation of c-myc, cyclin D1, cyclin A, and proliferating cell nuclear antigen. J Biol Chem. 2000 Dec 8;275(49):38261-7. doi: 10.1074/jbc.M005545200. [Article]
Cheng R, Liu YJ, Cui JW, Yang M, Liu XL, Li P, Wang Z, Zhu LZ, Lu SY, Zou L, Wu XQ, Li YX, Zhou Y, Fang ZY, Wei W: Aspirin regulation of c-myc and cyclinD1 proteins to overcome tamoxifen resistance in estrogen receptor-positive breast cancer cells. Oncotarget. 2017 May 2;8(18):30252-30264. doi: 10.18632/oncotarget.16325. [Article]
Ai G, Dachineni R, Muley P, Tummala H, Bhat GJ: Aspirin and salicylic acid decrease c-Myc expression in cancer cells: a potential role in chemoprevention. Tumour Biol. 2016 Feb;37(2):1727-38. doi: 10.1007/s13277-015-3959-0. Epub 2015 Aug 28. [Article]

Details17. Proliferating cell nuclear antigen

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Downregulator

General Function: Auxiliary protein of DNA polymerase delta and is involved in the control of eukaryotic DNA replication by increasing the polymerase's processibility during elongation of the leading strand. Induces a robust stimulatory effect on the 3'-5' exonuclease and 3'-phosphodiesterase, but not apurinic-apyrimidinic (AP) endonuclease, APEX2 activities. Has to be loaded onto DNA in order to be able to stimulate APEX2. Plays a key role in DNA damage response (DDR) by being conveniently positioned at the replication fork to coordinate DNA replication with DNA repair and DNA damage tolerance pathways (PubMed:24939902). Acts as a loading platform to recruit DDR proteins that allow completion of DNA replication after DNA damage and promote postreplication repair: Monoubiquitinated PCNA leads to recruitment of translesion (TLS) polymerases, while 'Lys-63'-linked polyubiquitination of PCNA is involved in error-free pathway and employs recombination mechanisms to synthesize across the lesion.
Specific Function: Chromatin binding
Gene Name: PCNA
Uniprot ID: P12004
Uniprot Name: Proliferating cell nuclear antigen
Molecular Weight: 28768.48 Da

References

Law BK, Waltner-Law ME, Entingh AJ, Chytil A, Aakre ME, Norgaard P, Moses HL: Salicylate-induced growth arrest is associated with inhibition of p70s6k and down-regulation of c-myc, cyclin D1, cyclin A, and proliferating cell nuclear antigen. J Biol Chem. 2000 Dec 8;275(49):38261-7. doi: 10.1074/jbc.M005545200. [Article]
Krishnan K, Aoki T, Ruffin MT, Normolle DP, Boland CR, Brenner DE: Effects of low dose aspirin (81 mg) on proliferating cell nuclear antigen and Amaranthus caudatus labeling in normal-risk and high-risk human subjects for colorectal cancer. Cancer Detect Prev. 2004;28(2):107-13. doi: 10.1016/j.cdp.2004.01.001. [Article]
Din FV, Valanciute A, Houde VP, Zibrova D, Green KA, Sakamoto K, Alessi DR, Dunlop MG: Aspirin inhibits mTOR signaling, activates AMP-activated protein kinase, and induces autophagy in colorectal cancer cells. Gastroenterology. 2012 Jun;142(7):1504-15.e3. doi: 10.1053/j.gastro.2012.02.050. Epub 2012 Mar 6. [Article]

18. Cyclin A

Kind

Group

Organism

Not Available

Pharmacological action

Unknown

Actions

Downregulator

References

Law BK, Waltner-Law ME, Entingh AJ, Chytil A, Aakre ME, Norgaard P, Moses HL: Salicylate-induced growth arrest is associated with inhibition of p70s6k and down-regulation of c-myc, cyclin D1, cyclin A, and proliferating cell nuclear antigen. J Biol Chem. 2000 Dec 8;275(49):38261-7. doi: 10.1074/jbc.M005545200. [Article]
Dachineni R, Ai G, Kumar DR, Sadhu SS, Tummala H, Bhat GJ: Cyclin A2 and CDK2 as Novel Targets of Aspirin and Salicylic Acid: A Potential Role in Cancer Prevention. Mol Cancer Res. 2016 Mar;14(3):241-52. doi: 10.1158/1541-7786.MCR-15-0360. Epub 2015 Dec 18. [Article]

Details19. Sialidase-1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Exo-alpha-sialidase activity
Specific Function: Catalyzes the removal of sialic acid (N-acetylneuraminic acid) moities from glycoproteins and glycolipids. To be active, it is strictly dependent on its presence in the multienzyme complex. Appears...
Gene Name: NEU1
Uniprot ID: Q99519
Uniprot Name: Sialidase-1
Molecular Weight: 45466.96 Da

References

Qorri B, Harless W, Szewczuk MR: Novel Molecular Mechanism of Aspirin and Celecoxib Targeting Mammalian Neuraminidase-1 Impedes Epidermal Growth Factor Receptor Signaling Axis and Induces Apoptosis in Pancreatic Cancer Cells. Drug Des Devel Ther. 2020 Oct 8;14:4149-4167. doi: 10.2147/DDDT.S264122. eCollection 2020. [Article]

Enzymes

Details1. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer
Curator comments: Data found in the literature regarding this enzyme action are currently limited to the results of one study.

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 Da

References

Chen XP, Tan ZR, Huang SL, Huang Z, Ou-Yang DS, Zhou HH: Isozyme-specific induction of low-dose aspirin on cytochrome P450 in healthy subjects. Clin Pharmacol Ther. 2003 Mar;73(3):264-71. doi: 10.1067/mcp.2003.14. [Article]

Details2. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Palikhe NS, Kim SH, Nam YH, Ye YM, Park HS: Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria. Allergy Asthma Immunol Res. 2011 Oct;3(4):273-6. doi: 10.4168/aair.2011.3.4.273. Epub 2011 Jul 1. [Article]

Details3. UDP-glucuronosyltransferase 1-6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Protein homodimerization activity
Specific Function: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks trans...
Gene Name: UGT1A6
Uniprot ID: P19224
Uniprot Name: UDP-glucuronosyltransferase 1-6
Molecular Weight: 60750.215 Da

References

Palikhe NS, Kim SH, Nam YH, Ye YM, Park HS: Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria. Allergy Asthma Immunol Res. 2011 Oct;3(4):273-6. doi: 10.4168/aair.2011.3.4.273. Epub 2011 Jul 1. [Article]
Chan AT, Tranah GJ, Giovannucci EL, Hunter DJ, Fuchs CS: Genetic variants in the UGT1A6 enzyme, aspirin use, and the risk of colorectal adenoma. J Natl Cancer Inst. 2005 Mar 16;97(6):457-60. doi: 10.1093/jnci/dji066. [Article]
Chen Y, Kuehl GE, Bigler J, Rimorin CF, Schwarz Y, Shen DD, Lampe JW: UGT1A6 polymorphism and salicylic acid glucuronidation following aspirin. Pharmacogenet Genomics. 2007 Aug;17(8):571-9. doi: 10.1097/01.fpc.0000236339.79916.07. [Article]

Details4. Arylamine N-acetyltransferase 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Arylamine n-acetyltransferase activity
Specific Function: Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivat...
Gene Name: NAT2
Uniprot ID: P11245
Uniprot Name: Arylamine N-acetyltransferase 2
Molecular Weight: 33542.235 Da

References

Palikhe NS, Kim SH, Nam YH, Ye YM, Park HS: Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria. Allergy Asthma Immunol Res. 2011 Oct;3(4):273-6. doi: 10.4168/aair.2011.3.4.273. Epub 2011 Jul 1. [Article]
McDonagh EM, Boukouvala S, Aklillu E, Hein DW, Altman RB, Klein TE: PharmGKB summary: very important pharmacogene information for N-acetyltransferase 2. Pharmacogenet Genomics. 2014 Aug;24(8):409-25. doi: 10.1097/FPC.0000000000000062. [Article]

Transporters

Details1. Solute carrier family 22 member 6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name: SLC22A6
Uniprot ID: Q4U2R8
Uniprot Name: Solute carrier family 22 member 6
Molecular Weight: 61815.78 Da

References

Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [Article]
Parvez MM, Shin HJ, Jung JA, Shin JG: Evaluation of para-Aminosalicylic Acid as a Substrate of Multiple Solute Carrier Uptake Transporters and Possible Drug Interactions with Nonsteroidal Anti-inflammatory Drugs In Vitro. Antimicrob Agents Chemother. 2017 Apr 24;61(5). pii: AAC.02392-16. doi: 10.1128/AAC.02392-16. Print 2017 May. [Article]

Details2. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inducer
Modulator

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [Article]
Li MP, Tang J, Zhang ZL, Chen XP: Induction of both P-glycoprotein and specific cytochrome P450 by aspirin eventually does not alter the antithrombotic effect of clopidogrel. Clin Pharmacol Ther. 2015 Apr;97(4):324. doi: 10.1002/cpt.32. Epub 2014 Dec 15. [Article]
Oh J, Shin D, Lim KS, Lee S, Jung KH, Chu K, Hong KS, Shin KH, Cho JY, Yoon SH, Ji SC, Yu KS, Lee H, Jang IJ: Aspirin decreases systemic exposure to clopidogrel through modulation of P-glycoprotein but does not alter its antithrombotic activity. Clin Pharmacol Ther. 2014 Jun;95(6):608-16. doi: 10.1038/clpt.2014.49. Epub 2014 Feb 24. [Article]
Kugai M, Uchiyama K, Tsuji T, Yoriki H, Fukui A, Qin Y, Higashimura Y, Mizushima K, Yoshida N, Katada K, Kamada K, Handa O, Takagi T, Konishi H, Yagi N, Yoshikawa T, Shirasaka Y, Tamai I, Naito Y, Itoh Y: MDR1 is related to intestinal epithelial injury induced by acetylsalicylic acid. Cell Physiol Biochem. 2013;32(4):942-50. doi: 10.1159/000354497. Epub 2013 Oct 1. [Article]
Flescher E, Rotem R, Kwon P, Azare J, Jaspers I, Cohen D: Aspirin enhances multidrug resistance gene 1 expression in human Molt-4 T lymphoma cells. Anticancer Res. 2000 Nov-Dec;20(6B):4441-4. [Article]

Details3. Solute carrier family 22 member 8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name: SLC22A8
Uniprot ID: Q8TCC7
Uniprot Name: Solute carrier family 22 member 8
Molecular Weight: 59855.585 Da

References

Parvez MM, Shin HJ, Jung JA, Shin JG: Evaluation of para-Aminosalicylic Acid as a Substrate of Multiple Solute Carrier Uptake Transporters and Possible Drug Interactions with Nonsteroidal Anti-inflammatory Drugs In Vitro. Antimicrob Agents Chemother. 2017 Apr 24;61(5). pii: AAC.02392-16. doi: 10.1128/AAC.02392-16. Print 2017 May. [Article]
Wang C, Wang C, Liu Q, Meng Q, Cang J, Sun H, Peng J, Ma X, Huo X, Liu K: Aspirin and probenecid inhibit organic anion transporter 3-mediated renal uptake of cilostazol and probenecid induces metabolism of cilostazol in the rat. Drug Metab Dispos. 2014 Jun;42(6):996-1007. doi: 10.1124/dmd.113.055194. Epub 2014 Apr 1. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Aspirin

Identification

Structure for Acetylsalicylic acid (DB00945)

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Properties

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Components:

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Enzymes

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Transporters

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