Indomethacin

Identification

Summary

Indomethacin is a nonsteroidal anti-inflammatory (NSAID) used for symptomatic management of chronic musculoskeletal pain conditions and to induce closure of a hemodynamically significant patent ductus arteriosus in premature infants.

Brand Names

Indocin, Tivorbex

Generic Name

Indomethacin

DrugBank Accession Number

DB00328

Background

Indometacin, or indomethacin, is a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic, and antipyretic properties. NSAIDs consist of agents that are structurally unrelated; the NSAID chemical classification of indometacin is an indole-acetic acid derivative with the chemical name 1- (p-chlorobenzoyl)25-methoxy-2-methylindole-3-acetic acid.¹ The pharmacological effect of indometacin is not fully understood, however, it is thought to be mediated through potent and nonselective inhibition of the enzyme cyclooxygenase (COX), which is the main enzyme responsible for catalyzes the rate-limiting step in prostaglandin and thromboxane biosynthesis via the arachidonic acid (AA) pathway. Indometacin was first discovered in 1963 and it was first approved for use in the U.S. by the Food and Drug Administration in 1965, ¹⁰ along with other acetic acid derivatives such as diclofenac and sulindac that were also developed during the 1960s.¹ Since then, indometacin has been extensively studied in clinical trials as one of the most potent NSAIDs in blocking prostaglandin synthesis and was among the first NSAIDs to be used in the symptomatic treatment of migraine and for headaches that eventually became known as “indomethacin-responsive” headache disorders.¹

Most commonly used in rheumatoid arthritis, ankylosing spondylitis, osteoarthritis, acute shoulder pains, and acute gouty arthritis, indometacin is currently available as oral capsules as well as other methods of administration, including rectal and intravenous formulations. Intravenous indometacin is administered to close a hemodynamically significant patent ductus arteriosus, as indicated by clinical evidence, in premature infants.¹⁴ Ophthalmic indometacin has been studied and used in the symptomatic treatment of postoperative ocular inflammation and pain and/or complications after cataract surgery. Although deemed effective in reducing ocular inflammation in clinical studies, topical NSAIDs were also associated with a potential reduction in corneal sensitivity accompanied by an increased risk of superficial punctate keratitis and subjective symptoms of discomfort, including pain, burning or pricking, or a tingling sensation after instillation into the cul‐de‐sac.⁶

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Indomethacin (DB00328)

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Weight

Average: 357.788
Monoisotopic: 357.076785712

Chemical Formula

C₁₉H₁₆ClNO₄

Synonyms

• {1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid
• 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid
• Indometacin
• Indometacina
• Indometacine
• Indometacinum
• Indomethacin

External IDs

• NSC-77541

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Pharmacology

Indication

Oral indometacin is indicated for symptomatic management of moderate to severe rheumatoid arthritis including acute flares of chronic disease, moderate to severe ankylosing spondylitis, moderate to severe osteoarthritis, acute painful shoulder (bursitis and/or tendinitis) and acute gouty arthritis.^1,13

Intravenous indometacin is indicated to induce closure of a hemodynamically significant patent ductus arteriosus in premature infants weighing between 500 and 1750 g when after 48 hours usual medical management (e.g., fluid restriction, diuretics, digitalis, respiratory support, etc.) is ineffective.¹⁴

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Acute gouty arthritis		••••••••••••
Used in combination to treat	Joint pain	Combination Product in combination with: Levomenthol (DB00825)	••• •••			•••
Management of	Moderate to severe osteoarthritis		••••••••••••
Management of	Moderate to severe rheumatoid arthritis		••••••••••••
Management of	Moderate to severe ankylosing spondylitis		••••••••••••

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Indometacin is an NSAID with analgesic and antipyretic properties that exerts its pharmacological effects by inhibiting the synthesis of factors involved in pain, fever, and inflammation. Its therapeutic action does not involve pituitary-adrenal stimulation.¹³ Indometacin primarily works by suppressing inflammation in rheumatoid arthritis by providing relief of pain as well as reducing fever, swelling, and tenderness. This effectiveness has been demonstrated by a reduction in the extent of joint swelling, the average number of joints displaying symptoms of inflammation, and the severity of morning stiffness. Increased mobility was demonstrated by a decrease in total walking time and by improved functional capability seen as an increase in grip strength.¹³ In clinical trials, indometacin was shown to be effective in relieving the pain, reducing the fever, swelling, redness, and tenderness of acute gouty arthritis. Due to its pharmacological actions, the use of indometacin is associated with the risk of serious cardiovascular thrombotic events, including myocardial infarction and stroke, as well as gastrointestinal effects such as bleeding, ulceration, and perforation of the stomach or intestines.¹³

In a study of healthy individuals, acute oral and intravenous indometacin therapy resulted in a transiently diminished basal and CO2 stimulated cerebral blood flow; this effect disappeared in one study after one week of oral treatment.¹³ The clinical significance of this effect has not been established. Compared to other NSAIDs, it is suggested that indometacin is a more potent vasoconstrictor that is more consistent in decreasing cerebral blood flow and inhibiting CO2 reactivity.¹ There have been studies that show indometacin directly inhibiting neuronal activity to some extent in the trigeminocervical complex after either superior salivatory nucleus or dural stimulation.¹

Mechanism of action

Indometacin is a nonspecific and reversible inhibitor of the cyclo-oxygenase (COX) enzyme or prostaglandin G/H synthase. There are two identified isoforms of COX: COX-1 is universally present in most body tissues and is involved in the synthesis of the prostaglandins and thromboxane A2, while COX-2 is expressed in response to injury or inflammation.¹ Constitutively expressed, the COX-1 enzyme is involved in gastric mucosal protection, platelet, and kidney function by catalyzing the conversion of arachidonic acid to prostaglandin (PG) G2 and PGG2 to PGH2.¹ COX-2 is constitutively expressed and highly inducible by inflammatory stimuli. It is found in the central nervous system, kidneys, uterus, and other organs. COX-2 also catalyzes the conversion of arachidonic acid to PGG2 and PGG2 to PGH2. In the COX-2-mediated pathway, PGH2 is further converted to PGE2 and PGI2 (also known as prostacyclin). PGE2 is involved in mediating inflammation, pain, and fever. Decreasing levels of PGE2 leads to reduced inflammatory reactions. Indometacin is known to inhibit both isoforms of COX, however, with greater selectivity for COX-1, which accounts for its increased adverse gastric effects relative to other NSAIDs. It binds to the enzyme's active site and prevents the interaction between the enzyme and its substrate, arachidonic acid. Indometacin, unlike other NSAIDs, also inhibits phospholipase A2, the enzyme responsible for releasing arachidonic acid from phospholipids. The analgesic, antipyretic and anti-inflammatory effects of indomethacin as well as adverse reactions associated with the drug occur as a result of decreased prostaglandin synthesis. Its antipyretic effects may be due to action on the hypothalamus, resulting in increased peripheral blood flow, vasodilation, and subsequent heat dissipation.

The exact mechanism of action of indometacin in inducing closure of a patent ductus arteriosus is not fully understood; however, it is thought to be through inhibition of prostaglandin synthesis.¹³ At birth, the ductus arteriosus is normally closed as the tension of the oxygen increases significantly after birth.⁴ Patent ductus arteriosus in premature infants is associated with congenital heart malformations where PGE1 mediates an opposite effect to that of oxygen. PGE1 dilates the ductus arteriosus through smooth muscle relaxation and prevents the closure of the ductus arteriosus.⁴ By inhibiting the synthesis of prostaglandins, indometacin promotes the closure of ductus arteriosus.¹⁴

Indometacin has been described as possessing anticancer and antiviral properties through activation of protein kinase R (PKR) and downstream phosphorylation of eIF2α, inhibiting protein synthesis.^11,12

Target	Actions	Organism
AProstaglandin G/H synthase 2	inhibitor	Humans
APhospholipase A2, membrane associated	inhibitor	Humans
UProstaglandin G/H synthase 1	inhibitor	Humans
UProstaglandin reductase 2	inhibitor	Humans
UPeroxisome proliferator-activated receptor gamma	activator	Humans
ULactoylglutathione lyase	inhibitor	Humans
UProstaglandin D2 receptor 2	other/unknown	Humans
UPeroxisome proliferator-activated receptor alpha	agonist	Humans
UAldo-keto reductase family 1 member C3	inhibitor	Humans
UInterferon-induced, double-stranded RNA-activated protein kinase	inducer	Humans
AHuman Cyclooxygenases	inhibitor	Humans

Absorption

Indometacin displays a linear pharmacokinetics profile where the plasma concentrations and area under the curve (AUC) are dose-proportional, whereas half-life (T1/2) and plasma and renal clearance are dose-dependent.¹ Indometacin is readily and rapidly absorbed from the gastrointestinal tract. The bioavailability is virtually 100% following oral administration ¹ and about 90% of the dose is absorbed within 4 hours.¹³ The bioavailability is about 80-90% following rectal administration.⁵

The peak plasma concentrations following a single oral dose were achieved between 0.9 ± 0.4 and 1.5 ± 0.8 hours in a fasting state.⁵ Despite large intersubject variation as well using the same preparation, peak plasma concentrations are dose-proportional and averaged 1.54 ± 0.76 μg/mL, 2.65 ± 1.03 μg/mL, and 4.92 ± 1.88 μg/mL following 25 mg, 50 mg, and 75 mg single doses in fasting subjects, respectively.⁵ With a typical therapeutic regimen of 25 or 50 mg t.i.d., the steady-state plasma concentrations of indomethacin are an average 1.4 times those following the first dose.¹³

Volume of distribution

The volume of distribution ranged from 0.34 to 1.57 L/kg following oral, intravenous, or rectal administration of single and multiple doses of indometacin in healthy individuals.⁷ Indometacin is distributed into the synovial fluid ² and is extensively bound to tissues ⁶. It has been detected in human breast milk ² and placenta.¹³ Although indometacin has been shown to cross the blood-brain barrier (BBB)¹³, its extensive plasma protein binding allows only the small fraction of free or unbound indometacin to diffuse across the BBB.⁶

Protein binding

Indometacin is a weak organic acid that is 90-99% bound to protein in plasma over the expected range of therapeutic plasma concentrations ^6,13. Like other NSAIDs, indometacin is bound to plasma albumin ⁶ but it does not bind to red blood cells. ²

Metabolism

Indometacin undergoes hepatic metabolism involving glucuronidation, O-desmethylation, and N-deacylation.⁶ O-desmethyl-indomethacin, N-deschlorobenzoyl-indomethacin, and O-desmethyl-N-deschlorobenzoyl-indomethacin metabolites and their glucuronides are primarily inactive and have no pharmacological activity.^6,13 Unconjugated metabolites are also detected in the plasma.¹³ Its high bioavailability indicates that indometacin is unlikely to be subject to the first-pass metabolism.⁶

Hover over products below to view reaction partners

• Indomethacin
  • 5-Hydroxyindomethacin
  • Indomethacin acyl glucuronide
  • Deacyl indomethacin
    • O-Desmethyl-N-deschlorobenzoyl indomethacin

Route of elimination

Indometacin is eliminated via renal excretion, metabolism, and biliary excretion. It is also subject to enter the enterohepatic circulation through excretion of its glucuronide metabolites into bile followed by resorption of indometacin after hydrolysis ⁶. The extent of involvement in the enterohepatic circulation ranges from 27 to 115%.⁶

About 60 percent of an oral dosage is recovered in urine as drug and metabolites (26 percent as indomethacin and its glucuronide), and 33 percent in the feces (1.5 percent as indomethacin).¹³

Half-life

Indometacin disposition from the plasma is reported to be biphasic, with a half-life of 1 hour during the initial phase and 2.6–11.2 hours during the second phase.⁶ Interindividual and intraindividual variations are possible due to the extensive and sporadic nature of the enterohepatic recycling and biliary discharge of the drug.^2,6

The mean half-life of oral indomethacin is estimated to be about 4.5 hours.¹³ The disposition of intravenous indometacin in preterm neonates was shown to vary across premature infants. In neonates older than 7 days, the mean plasma half-life of intravenous indometacin was approximately 20 hours, ranging from 15 hours in infants weighing more than 1000 g and 21 hours in infants weighing less than 1000 g.¹⁴

Clearance

In a clinical pharmacokinetic study, the plasma clearance of indometacin was reported to range from 1 to 2.5 mL/kg/min following oral administration.²

Adverse Effects

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Toxicity

Acute oral LD50 is 2.42 mg/kg in rats and 13 mg/kg in mice.^MSDS The oral LD50 of indomethacin in mice and rats (based on 14-day mortality response) was 50 and 12 mg/kg, respectively.¹³

Symptoms of overdose may be characterized by nausea, vomiting, intense headache, dizziness, mental confusion, disorientation, or lethargy. In addition, there have been reports of paresthesias, numbness, and convulsions. In case of an overdose, the patient should receive symptomatic and supportive treatment with stomach emptying through induced vomiting or gastric lavage.¹³ The patient should then be closely monitored for any signs of gastrointestinal ulceration and hemorrhage. Antacids may be useful.¹³

Pathways

Pathway	Category
Indomethacin Action Pathway	Drug action

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Interactions

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	The metabolism of Abacavir can be decreased when combined with Indomethacin.
Abatacept	The metabolism of Indomethacin can be increased when combined with Abatacept.
Abciximab	The risk or severity of bleeding and hemorrhage can be increased when Indomethacin is combined with Abciximab.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Indomethacin.
Acamprosate	The excretion of Acamprosate can be decreased when combined with Indomethacin.

Food Interactions

• Avoid alcohol. Ingestion of alcohol can increase the risk of GI bleeding.
• Take with or without food. Food has no effect on drug absorption. However, food may decrease the extent of gastrointestinal irritation caused by indomethacin.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Indomethacin sodium	0IMX38M2GG	74252-25-8	UHYAQBLOGVNWNT-UHFFFAOYSA-M

Product Images

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International/Other Brands

Aconip (Teika Pharmaceutical Co.,Ltd.) / Arthrexin (Alphapharm) / Elmetacin (Sankyo) / Indaflex (Andromaco) / Indocid (Lundbeck) / Indolar SR (Sandoz) / Indomed (Greater Pharma) / Indoxen (Quality Pharmaceutical) / Metindol (GlaxoSmithKline) / Mikametan (Mikasa Seiyaku) / Nu-Indo (Nu-Pharm) / Reumacide (Vitória)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Indocid Cap 25mg	Capsule	25 mg / cap	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1965-12-31	1998-08-14
Indocid Cap 50mg	Capsule	50 mg / cap	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1970-12-31	1998-08-14
Indocid SR 75mg	Capsule, extended release	75 mg / cap	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1980-12-31	1999-08-06
Indocid Sterile Oph Susp 1%	Solution / drops	10 mg / mL	Ophthalmic	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1983-12-31	1999-08-06
Indocid Sup 100mg	Suppository	100 mg / sup	Rectal	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1971-12-31	2003-08-08

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Apo-indomethacin	Capsule	50 mg	Oral	Apotex Corporation	1984-12-31	Not applicable
Apo-indomethacin	Capsule	25 mg	Oral	Apotex Corporation	1984-12-31	Not applicable
Auro-indomethacin	Capsule	50 mg	Oral	Auro Pharma Inc	2021-07-08	Not applicable
Ftp-indomethacin	Capsule	25 mg / cap	Oral	Ftp Pharmacal Inc.	1998-10-09	2004-08-03
Ftp-indomethacin	Capsule	50 mg / cap	Oral	Ftp Pharmacal Inc.	1998-10-09	2004-08-03

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
ELMETACIN	Spray	8 mg/1ml	Topical	บริษัท ดีเคเอสเอช (ประเทศไทย) จำกัด	2007-10-15	2020-10-05
เอ็ม-ซิน	Spray	8 mg/1ml	Topical	บริษัท แมคโครฟาร์ จำกัด	2007-04-05	Not applicable
เอลมีโก สเปรย์	Spray	8 mg/1ml	Topical	บริษัท โรงงานผลิตเวชภัณฑ์ชินต้าเทรดดิ้ง (1971) จำกัด จำกัด	1998-12-21	Not applicable
เอลเมทาซิน	Spray	8 mg/1ml	Topical	บริษัท โอลิค (ประเทศไทย) จำกัด	1987-04-14	Not applicable
แวนเทลินโคว่า ครีม	Cream	1 %w/w	Topical	บริษัท โคว่า (ประเทศไทย) จำกัด	2017-12-23	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
DIFMETRE	Indomethacin (25 mg) + Caffeine (75 mg) + Prochlorperazine maleate (4 mg)	Suppository		Mylan Italia S.R.L.	2014-07-08	Not applicable
DIFMETRE	Indomethacin (25 mg) + Caffeine (75 mg) + Prochlorperazine maleate (2 mg)	Tablet		Viatris Italia S.R.L.	2014-07-08	2023-10-01
DIFMETRE	Indomethacin (25 mg) + Caffeine (75 mg) + Prochlorperazine maleate (2 mg)	Tablet		Mylan Italia S.R.L.	2014-07-08	Not applicable
DIFMETRE	Indomethacin (50 mg) + Caffeine (150 mg) + Prochlorperazine maleate (8 mg)	Suppository		Mylan Italia S.R.L.	2014-07-08	Not applicable
DIFMETRE	Indomethacin (25 mg) + Caffeine (75 mg) + Prochlorperazine maleate (2 mg)	Tablet		Mylan Italia S.R.L.	2014-07-08	Not applicable

Categories

ATC Codes

S01CC02 — Indometacin and antiinfectives

• S01CC — Antiinflammatory agents, non-steroids and antiinfectives in combination
• S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION
• S01 — OPHTHALMOLOGICALS
• S — SENSORY ORGANS

M01AB51 — Indometacin, combinations

• M01AB — Acetic acid derivatives and related substances
• M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
• M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
• M — MUSCULO-SKELETAL SYSTEM

S01BC01 — Indometacin

• S01BC — Antiinflammatory agents, non-steroids
• S01B — ANTIINFLAMMATORY AGENTS
• S01 — OPHTHALMOLOGICALS
• S — SENSORY ORGANS

M02AA23 — Indometacin

• M02AA — Antiinflammatory preparations, non-steroids for topical use
• M02A — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
• M02 — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
• M — MUSCULO-SKELETAL SYSTEM

M01AB01 — Indometacin

• M01AB — Acetic acid derivatives and related substances
• M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
• M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
• M — MUSCULO-SKELETAL SYSTEM

C01EB03 — Indometacin

• C01EB — Other cardiac preparations
• C01E — OTHER CARDIAC PREPARATIONS
• C01 — CARDIAC THERAPY
• C — CARDIOVASCULAR SYSTEM

Drug Categories

• Acetic Acid Derivatives and Related Substances
• Agents causing hyperkalemia
• Agents that produce hypertension
• Analgesics
• Analgesics, Non-Narcotic
• Anti-Inflammatory Agents
• Anti-Inflammatory Agents, Non-Steroidal
• Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
• Antigout Preparations
• Antiinflammatory and Antirheumatic Products
• Antiinflammatory and Antirheumatic Products, Non-Steroids
• Antiinflammatory Preparations, Non-Steroids for Topical Use
• Antirheumatic Agents
• BSEP/ABCB11 Substrates
• Cardiac Therapy
• Cardiovascular Agents
• Central Nervous System Agents
• Cyclooxygenase Inhibitors
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
• Cytochrome P-450 CYP2C19 Substrates
• Cytochrome P-450 CYP2C9 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Enzyme Inhibitors
• Heterocyclic Compounds, Fused-Ring
• Hypoglycemia-Associated Agents
• Immunosuppressive Agents
• Indoles
• Musculo-Skeletal System
• Myelosuppressive Agents
• Nephrotoxic agents
• Non COX-2 selective NSAIDS
• OAT1/SLC22A6 inhibitors
• OAT1/SLC22A6 Substrates
• OAT3/SLC22A8 Inhibitors
• OAT3/SLC22A8 Substrates
• OATP1B1/SLCO1B1 Inhibitors
• Ophthalmologicals
• Other Nonsteroidal Anti-inflammatory Agents
• P-glycoprotein inhibitors
• P-glycoprotein substrates
• Peripheral Nervous System Agents
• Sensory Organs
• Sensory System Agents
• Tocolytic Agents
• Topical Products for Joint and Muscular Pain
• UGT1A1 Inhibitors
• UGT1A1 Substrates
• UGT1A9 Substrates
• UGT2B7 Inhibitors
• UGT2B7 substrates

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Benzoylindoles

Direct Parent

Benzoylindoles

Alternative Parents

Indole-3-acetic acid derivatives / Indolecarboxylic acids and derivatives / 3-alkylindoles / 4-halobenzoic acids and derivatives / Anisoles / Benzoyl derivatives / Alkyl aryl ethers / Chlorobenzenes / Substituted pyrroles / Aryl chlorides / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Azacyclic compounds / Carboxylic acids / Organonitrogen compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Organochlorides

show 10 more

Substituents

3-alkylindole / 4-halobenzoic acid or derivatives / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Benzoic acid or derivatives / Benzoyl / Benzoylindole / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Chlorobenzene / Ether / Halobenzene / Halobenzoic acid or derivatives / Heteroaromatic compound / Hydrocarbon derivative / Indole / Indole-3-acetic acid derivative / Indolecarboxylic acid derivative / Indolyl carboxylic acid derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organochloride / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Pyrrole / Substituted pyrrole

show 27 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether, monochlorobenzenes, N-acylindole, indole-3-acetic acids (CHEBI:49662) / a small molecule (CPD-10545)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

XXE1CET956

CAS number

53-86-1

InChI Key

CGIGDMFJXJATDK-UHFFFAOYSA-N

InChI

InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)

IUPAC Name

2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid

SMILES

COC1=CC2=C(C=C1)N(C(=O)C1=CC=C(Cl)C=C1)C(C)=C2CC(O)=O

References

Synthesis Reference

Hubertus L. Regtop, John R. Biffin, "Preparation of divalent metal salts of indomethacin." U.S. Patent US5310936, issued November, 1917.

US5310936

General References

1. Lucas S: The Pharmacology of Indomethacin. Headache. 2016 Feb;56(2):436-46. doi: 10.1111/head.12769. Epub 2016 Feb 11. [Article]
2. Helleberg L: Clinical Pharmacokinetics of indomethacin. Clin Pharmacokinet. 1981 Jul-Aug;6(4):245-58. doi: 10.2165/00003088-198106040-00001. [Article]
3. Nalamachu S, Wortmann R: Role of indomethacin in acute pain and inflammation management: a review of the literature. Postgrad Med. 2014 Jul;126(4):92-7. doi: 10.3810/pgm.2014.07.2787. [Article]
4. Pacifici GM: Clinical pharmacology of indomethacin in preterm infants: implications in patent ductus arteriosus closure. Paediatr Drugs. 2013 Oct;15(5):363-76. doi: 10.1007/s40272-013-0031-7. [Article]
5. Jensen KM, Grenabo L: Bioavailability of indomethacin after intramuscular injection and rectal administration of solution and suppositories. Acta Pharmacol Toxicol (Copenh). 1985 Nov;57(5):322-7. [Article]
6. Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. [Article]
7. Alvan G, Orme M, Bertilsson L, Ekstrand R, Palmer L: Pharmacokinetics of indomethacin. Clin Pharmacol Ther. 1975 Sep;18(3):364-73. [Article]
8. Ricciotti E, FitzGerald GA: Prostaglandins and inflammation. Arterioscler Thromb Vasc Biol. 2011 May;31(5):986-1000. doi: 10.1161/ATVBAHA.110.207449. [Article]
9. Rouzer CA, Marnett LJ: Cyclooxygenases: structural and functional insights. J Lipid Res. 2009 Apr;50 Suppl:S29-34. doi: 10.1194/jlr.R800042-JLR200. Epub 2008 Oct 23. [Article]
10. HART FD, BOARDMAN PL: INDOMETHACIN: A NEW NON-STEROID ANTI-INFLAMMATORY AGENT. Br Med J. 1963 Oct 19;2(5363):965-70. [Article]
11. Brunelli C, Amici C, Angelini M, Fracassi C, Belardo G, Santoro MG: The non-steroidal anti-inflammatory drug indomethacin activates the eIF2alpha kinase PKR, causing a translational block in human colorectal cancer cells. Biochem J. 2012 Apr 15;443(2):379-86. doi: 10.1042/BJ20111236. [Article]
12. Amici C, La Frazia S, Brunelli C, Balsamo M, Angelini M, Santoro MG: Inhibition of viral protein translation by indomethacin in vesicular stomatitis virus infection: role of eIF2alpha kinase PKR. Cell Microbiol. 2015 Sep;17(9):1391-404. doi: 10.1111/cmi.12446. Epub 2015 May 13. [Article]
13. Indomethacin Capsules (25 mg) - FDA Label [Link]
14. Indocin I.V. (indomethacin for injection) - FDA Label [Link]
15. FDA Approved Drug Products: INDOCIN (indomethacin) Suppositories, for rectal use [Link]

External Links

Human Metabolome Database

HMDB0014473

KEGG Drug

D00141

KEGG Compound

C01926

PubChem Compound

3715

PubChem Substance

46508291

ChemSpider

3584

BindingDB

17638

RxNav

5781

ChEBI

49662

ChEMBL

CHEMBL6

ZINC

ZINC000000601283

Therapeutic Targets Database

DAP000617

PharmGKB

PA449982

Guide to Pharmacology

GtP Drug Page

PDBe Ligand

IMN

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Indometacin

PDB Entries

1s2a / 1z9h / 2bxk / 2bxm / 2bxq / 2dm6 / 2oth / 2zb8 / 3ads / 3adx …

show 14 more

MSDS

Download (73.2 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Healthy, Male / Neuromuscular Function	2
4	Completed	Prevention	Acute Pancreatitis	1
4	Completed	Prevention	Cataracts / Inflammation	1
4	Completed	Prevention	Family Planning	1
4	Completed	Prevention	Healthy Subjects (HS)	1

Pharmacoeconomics

Manufacturers

• Iroko pharmaceuticals llc
• Sandoz inc
• Able laboratories inc
• Avanthi inc
• Inwood laboratories inc sub forest laboratories inc
• Teva pharmaceuticals usa inc
• Duramed pharmaceuticals inc sub barr laboratories inc
• Halsey drug co inc
• Heritage pharmaceuticals inc
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• Mutual pharmaceutical co inc
• Mylan pharmaceuticals inc
• Parke davis div warner lambert co
• Pioneer pharmaceuticals inc
• Pliva inc
• Roxane laboratories inc
• Superpharm corp
• Vintage pharmaceuticals llc
• Watson laboratories inc
• App pharmaceuticals llc
• G and w laboratories inc
• Lundbeck inc
• Bedford laboratories div ben venue laboratories inc

Packagers

• Advanced Pharmaceutical Services Inc.
• Amerisource Health Services Corp.
• Apotheca Inc.
• Apothecary Shop Wholesale
• A-S Medication Solutions LLC
• Bedford Labs
• Bryant Ranch Prepack
• Cardinal Health
• Caremark LLC
• Central Texas Community Health Centers
• Comprehensive Consultant Services Inc.
• DHHS Program Support Center Supply Service Center
• Direct Dispensing Inc.
• Dispensing Solutions
• Emcure Pharmaceuticals Ltd.
• Endo Pharmaceuticals Inc.
• Eon Labs
• G & W Labs
• Group Health Cooperative
• H.J. Harkins Co. Inc.
• Heartland Repack Services LLC
• Inwood Labs
• Iroko Pharmaceuticals
• Kaiser Foundation Hospital
• KVK-Tech Inc.
• Lake Erie Medical and Surgical Supply
• Liberty Pharmaceuticals
• Lundbeck Inc.
• Major Pharmaceuticals
• Medisca Inc.
• Medvantx Inc.
• Merck & Co.
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Novopharm Ltd.
• Nucare Pharmaceuticals Inc.
• Palmetto Pharmaceuticals Inc.
• Patient First Corp.
• PCA LLC
• PD-Rx Pharmaceuticals Inc.
• Pharmedix
• Physicians Total Care Inc.
• Pliva Inc.
• Preferred Pharmaceuticals Inc.
• Prepackage Specialists
• Prescription Dispensing Service Inc.
• Qualitest
• Rebel Distributors Corp.
• Redpharm Drug
• Remedy Repack
• Sandhills Packaging Inc.
• Sandoz
• Southwood Pharmaceuticals
• St Mary's Medical Park Pharmacy
• Talbert Medical Management Corp.
• Teva Pharmaceutical Industries Ltd.
• Tya Pharmaceuticals
• UDL Laboratories
• United Research Laboratories Inc.
• Veratex Corp.

Dosage Forms

Form	Route	Strength
Capsule	Oral	60.0000 mg
Capsule	Oral
Suppository
Tablet
Capsule	Oral	25.000 mg
Capsule, coated pellets	Oral	75 mg
Capsule	Oral	25.00 MG
Cream	Cutaneous	2.500 g
Capsule, extended release	Oral	75 MG
Solution / drops	Ophthalmic
Suppository	Rectal	100.000 mg
Capsule	Oral
Capsule	Oral	25 mg / cap
Capsule, extended release	Oral	75 mg / cap
Solution / drops	Ophthalmic	10 mg / mL
Injection, powder, lyophilized, for solution	Intravenous	1 mg
Injection, powder, lyophilized, for solution	Intravenous	1 mg/1
Suppository	Rectal	50 mg/1
Suspension	Oral	25 mg/5mL
Solution / drops	Ophthalmic	0.1 %
Solution / drops	Ophthalmic	1 MG/ML
Liquid; powder, for solution	Ophthalmic	1 mg / 1 mL
Solution / drops	Ophthalmic
Solution / drops	Ophthalmic	5 MG/ML
Capsule	Oral	25 mg/1
Capsule	Oral	50 mg/1
Capsule, extended release	Oral	75 mg/1
Injection, powder, for solution	Intravenous	0.1 mg/0.1mL
Injection, powder, lyophilized, for solution	Intravenous	1 mg/1mL
Capsule	Oral	75 mg/1
Capsule, coated pellets	Oral
Injection, powder, for solution	Intravenous; Parenteral	25 MG/2ML
Injection, powder, for solution	Intravenous; Parenteral	50 MG/2ML
Capsule, extended release	Oral
Suppository	Rectal
Solution	Intravenous	1.00 mg
Solution	Topical
Gel	Cutaneous
Capsule, liquid filled	Oral	25 mg
Suppository	Rectal	100 mg / sup
Suppository	Rectal	50 mg / sup
Suppository	Rectal	100 mg
Suppository	Rectal	50 mg
Capsule	Oral	50 mg / cap
Tablet	Oral
Gel	Cutaneous	500.000 mg
Gel	Topical
Capsule	Oral	20 mg/1
Capsule	Oral	40 mg/1
Capsule
Capsule	Oral	25 mg
Tablet		25 mg
Tablet, sugar coated	Oral	25 mg
Tablet, film coated		25 mg
Tablet, film coated		50 mg
Capsule	Oral	50 mg
Tablet, coated	Oral	25 mg
Spray	Topical	8 mg/1ml
Cream	Topical	1 %w/w

Prices

Unit description	Cost	Unit
Indocin i.v. 1 mg vial	642.6USD	vial
Indomethacin 1 mg vial	600.0USD	vial
Indocin 50 mg suppository	9.56USD	suppository
Indomethacin CR 75 mg capsule	3.12USD	capsule
Indocin sr 75 mg capsule	2.92USD	capsule
Indomethacin powder	2.57USD	g
Ratio-Indomethacin 100 mg Suppository	0.93USD	suppository
Sandoz Indomethacin 100 mg Suppository	0.93USD	suppository
Sandoz Indomethacin 50 mg Suppository	0.93USD	suppository
Indomethacin 50 mg capsule	0.65USD	capsule
Indomethacin 25 mg capsule	0.44USD	capsule
Apo-Indomethacin 50 mg Capsule	0.16USD	capsule
Novo-Methacin 50 mg Capsule	0.16USD	capsule
Nu-Indo 50 mg Capsule	0.16USD	capsule
Apo-Indomethacin 25 mg Capsule	0.09USD	capsule
Novo-Methacin 25 mg Capsule	0.09USD	capsule
Nu-Indo 25 mg Capsule	0.09USD	capsule

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

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US9089471	No	2015-07-28	2030-04-23
US8992982	No	2015-03-31	2030-04-23
US8734847	No	2014-05-27	2030-04-23

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	151	U.S. Patent 3,161,654.
water solubility	0.937 mg/L (at 25 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	4.27	HANSCH,C ET AL. (1995)
logS	-4.62	ADME Research, USCD
Caco2 permeability	-4.69	ADME Research, USCD
pKa	4.5	BUDAVARI,S ET AL. (1989)

Predicted Properties

Property	Value	Source
Water Solubility	0.0024 mg/mL	ALOGPS
logP	4.25	ALOGPS
logP	3.53	Chemaxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	3.79	Chemaxon
pKa (Strongest Basic)	-2.9	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	68.53 Å2	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	94.81 m3·mol-1	Chemaxon
Polarizability	36.64 Å3	Chemaxon
Number of Rings	3	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	+	0.9509
Blood Brain Barrier	+	0.9381
Caco-2 permeable	+	0.5857
P-glycoprotein substrate	Non-substrate	0.636
P-glycoprotein inhibitor I	Non-inhibitor	0.9313
P-glycoprotein inhibitor II	Non-inhibitor	0.834
Renal organic cation transporter	Non-inhibitor	0.8334
CYP450 2C9 substrate	Non-substrate	0.712
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.6436
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9302
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.8309
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.6978
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.8728
Biodegradation	Not ready biodegradable	0.9743
Rat acute toxicity	4.0722 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9818
hERG inhibition (predictor II)	Non-inhibitor	0.8306

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

Spectra

Mass Spec (NIST)

Download (7.7 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-000i-0921000000-71472b2fb43c8acb2e55
GC-MS Spectrum - EI-B	GC-MS	splash10-002f-9100000000-2545b33ef519ca9557d7
Mass Spectrum (Electron Ionization)	MS	splash10-000i-1901000000-710010c41f0ded9b0f17
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-000i-2902000000-8effecdaf737eb86e781
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-000i-0901000000-aa0cdbd9e10c432d837c
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-014u-2900000000-3bf048feb0cc9b0867e8
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-03di-0009000000-5a4abda1542473813a5d
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-03di-0019000000-b80206e17a22fdf15299
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0002-0093000000-4e04725a4a7ea8db1880
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0bt9-0906000000-44825d096b6f8c6091ab
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-053r-0890000000-e9f8e33084842b2a91e0
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-5aee2869a858e70aa8cb
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-5aee2869a858e70aa8cb
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-03di-0019000000-b9916635c4db449698ab
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0002-0092000000-270cd44f32c881ded6aa
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4j-0973000000-6e9ac766080e35c8b297
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-053r-0790000000-b0e6139fc1746c17ddb7
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-1df95eb7ff5058a870cc
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-03di-0009000000-6a65e96ca253d6a3dda0
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-08gi-0195000000-7ea82149ddaa783e01df
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0900000000-1208c0d5e605b8b69605
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4r-0709000000-1814b324e15b59fa31a5
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0900000000-da84cf2df3db68610ae6
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0900000000-f05d502a85960fefa1b3
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0900000000-ef4bc1155685673e5c96
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-1900000000-f3d47b27b5deef302e24
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-1900000000-529c521348d72ac3ac2c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4r-0709000000-552147af435f6203b275
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0900000000-3ecb36f2b39a0a31490e
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0900000000-3f989b1435664e5bd1c9
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0900000000-432dc50c7beda844e96f
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-0900000000-3a2c27afaa406477bb36
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-000i-1900000000-30707a04c6d14ccc1494
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0900000000-ceb3b04d9de59607c950
MS/MS Spectrum - , positive	LC-MS/MS	splash10-000i-2902000000-8effecdaf737eb86e781
MS/MS Spectrum - , positive	LC-MS/MS	splash10-000i-0901000000-aa0cdbd9e10c432d837c
MS/MS Spectrum - , positive	LC-MS/MS	splash10-000i-3900000000-353e94b605ae82792fae
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000i-0901000000-5c9675c7c76c033ffc5b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0009000000-7a21f3ce0463915fd604
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0009000000-aa85475b506e40224aaf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4r-0839000000-de3bcfe4027e9454d01f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-053r-8029000000-769e2411f9d152f46d93
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052r-0910000000-91e7cbb2a0c96149d304
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-9010000000-5177a0b85e9459459e27
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0009000000-7a21f3ce0463915fd604
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0009000000-aa85475b506e40224aaf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4r-0839000000-de3bcfe4027e9454d01f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-053r-8029000000-769e2411f9d152f46d93
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052r-0910000000-91e7cbb2a0c96149d304
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-9010000000-5177a0b85e9459459e27
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

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	191.8318517	predicted	DarkChem Lite v0.1.0
[M-H]-	192.3842517	predicted	DarkChem Lite v0.1.0
[M-H]-	192.0699517	predicted	DarkChem Lite v0.1.0
[M-H]-	181.18584	predicted	DeepCCS 1.0 (2019)
[M-H]-	191.8318517	predicted	DarkChem Lite v0.1.0
[M-H]-	192.3842517	predicted	DarkChem Lite v0.1.0
[M-H]-	192.0699517	predicted	DarkChem Lite v0.1.0
[M-H]-	181.18584	predicted	DeepCCS 1.0 (2019)
[M+H]+	192.2708517	predicted	DarkChem Lite v0.1.0
[M+H]+	193.6368517	predicted	DarkChem Lite v0.1.0
[M+H]+	192.5201517	predicted	DarkChem Lite v0.1.0
[M+H]+	183.56938	predicted	DeepCCS 1.0 (2019)
[M+H]+	192.2708517	predicted	DarkChem Lite v0.1.0
[M+H]+	193.6368517	predicted	DarkChem Lite v0.1.0
[M+H]+	192.5201517	predicted	DarkChem Lite v0.1.0
[M+H]+	183.56938	predicted	DeepCCS 1.0 (2019)
[M+Na]+	192.1285517	predicted	DarkChem Lite v0.1.0
[M+Na]+	193.4278517	predicted	DarkChem Lite v0.1.0
[M+Na]+	192.0808517	predicted	DarkChem Lite v0.1.0
[M+Na]+	191.20998	predicted	DeepCCS 1.0 (2019)
[M+Na]+	192.1285517	predicted	DarkChem Lite v0.1.0
[M+Na]+	193.4278517	predicted	DarkChem Lite v0.1.0
[M+Na]+	192.0808517	predicted	DarkChem Lite v0.1.0
[M+Na]+	191.20998	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	900	N/A	N/A	A27773 / A27776 / A27778 / A27789
IC 50 (nM)	180000	N/A	N/A	A27774
IC 50 (nM)	1200	N/A	N/A	A27775
IC 50 (nM)	560	N/A	N/A	A27777
IC 50 (nM)	165000	N/A	N/A	A27759
IC 50 (nM)	500	N/A	N/A	A27779 / A27782 / A27760 / A27785 / A27786 / A27768 / A27815
IC 50 (nM)	26	N/A	N/A	A27779 / A27785 / A27786
IC 50 (nM)	5800	N/A	N/A	A27780 / A27781 / A27799
IC 50 (nM)	30	N/A	N/A	A27760 / A27791
IC 50 (nM)	400	N/A	N/A	A27784
IC 50 (nM)	750	8	37	A5934
IC 50 (nM)	220	N/A	N/A	A27761
IC 50 (nM)	410	N/A	N/A	A27787
IC 50 (nM)	750	N/A	N/A	A27788 / A27811 / A27770
IC 50 (nM)	9	N/A	N/A	A27792 / A27795
IC 50 (nM)	2400	N/A	N/A	A27793
IC 50 (nM)	5.9	N/A	N/A	A27794
IC 50 (nM)	630	N/A	N/A	A27794
IC 50 (nM)	2380	N/A	N/A	A27762
IC 50 (nM)	640	N/A	N/A	A27795
IC 50 (nM)	7800	N/A	N/A	A27796
IC 50 (nM)	440	N/A	N/A	A27797
IC 50 (nM)	730	N/A	N/A	A27797
IC 50 (nM)	7810	N/A	N/A	A27798
IC 50 (nM)	3900	N/A	N/A	A27763
IC 50 (nM)	36	N/A	N/A	A27800
IC 50 (nM)	10	N/A	N/A	A27801 / A27805 / A27812
IC 50 (nM)	77100	N/A	N/A	A27764
IC 50 (nM)	2630	N/A	N/A	A27802 / A27806
IC 50 (nM)	700	N/A	N/A	A27765
IC 50 (nM)	11000	N/A	N/A	A27766
IC 50 (nM)	2.63E+03	N/A	N/A	A27767
IC 50 (nM)	40	N/A	N/A	A27803
IC 50 (nM)	600	N/A	N/A	A27804
IC 50 (nM)	670	N/A	N/A	A27769
IC 50 (nM)	35200	N/A	N/A	A27807
IC 50 (nM)	6900	N/A	N/A	A27808 / A27814
IC 50 (nM)	1900	N/A	N/A	A27809
IC 50 (nM)	17000	N/A	N/A	A27810
IC 50 (nM)	5700	N/A	N/A	A27813
IC 50 (nM)	48	N/A	N/A	A27816
IC 50 (nM)	18300	N/A	N/A	A27817
Ki (nM)	370	N/A	N/A	A5629
Ki (nM)	1000	N/A	N/A	A27471
Ki (nM)	130	N/A	N/A	A27471
Ki (nM)	440	N/A	N/A	A27783 / A27790
Ki (nM)	600	N/A	N/A	A27783 / A27790
Ki (nM)	400	N/A	N/A	A27783 / A27790

Details

Binding Properties1. Prostaglandin G/H synthase 2

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

Curator comments

IC50 = 0.48 microM

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

1. Armstrong PJ, Franklin DP, Carey DJ, Elmore JR: Suppression of experimental aortic aneurysms: comparison of inducible nitric oxide synthase and cyclooxygenase inhibitors. Ann Vasc Surg. 2005 Mar;19(2):248-57. [Article]
2. Jerde TJ, Calamon-Dixon JL, Bjorling DE, Nakada SY: Celecoxib inhibits ureteral contractility and prostanoid release. Urology. 2005 Jan;65(1):185-90. [Article]
3. Pilane CM, Labelle EF: Nitric oxide stimulated vascular smooth muscle cells undergo apoptosis induced in part by arachidonic acid derived eicosanoids. J Cell Physiol. 2005 Aug;204(2):423-7. [Article]
4. Yokota A, Taniguchi M, Takahira Y, Tanaka A, Takeuchi K: Rofecoxib produces intestinal but not gastric damage in the presence of a low dose of indomethacin in rats. J Pharmacol Exp Ther. 2005 Jul;314(1):302-9. Epub 2005 Apr 14. [Article]
5. Zhang GS, Fu YB, Xia M: [Proliferation inhibition effect of indomethacin on CML cells associated with down-regulation of phosphorylated STAT1/STAT5 and inhibition of COX-2 expression]. Zhonghua Xue Ye Xue Za Zhi. 2004 Dec;25(12):732-5. [Article]
6. Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [Article]

Details2. Phospholipase A2, membrane associated

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Phospholipid binding

Specific Function

Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-ph...

Gene Name

PLA2G2A

Uniprot ID

P14555

Uniprot Name

Phospholipase A2, membrane associated

Molecular Weight

16082.525 Da

References

1. Geisslinger, G., & Lötsch, J. (2004). Non-steroidal anti-inflammatory drugs. In Encyclopedic reference of molecular pharmacology (pp. 667-671). Berlin: Springer. [ISBN:9783540298328]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	1400	N/A	N/A	A27759
IC 50 (nM)	20	N/A	N/A	A27760 / A27771
IC 50 (nM)	200	N/A	N/A	A27760 / A27768
IC 50 (nM)	250	N/A	N/A	A27761
IC 50 (nM)	150	N/A	N/A	A27762
IC 50 (nM)	10	N/A	N/A	A27763
IC 50 (nM)	5600	N/A	N/A	A27764
IC 50 (nM)	500	N/A	N/A	A27765
IC 50 (nM)	100	N/A	N/A	A27766
IC 50 (nM)	2.60E+02	N/A	N/A	A27767
IC 50 (nM)	6000	N/A	N/A	A27768
IC 50 (nM)	50	N/A	N/A	A27769 / A27770
IC 50 (nM)	44	N/A	N/A	A27499

Details

Binding Properties3. Prostaglandin G/H synthase 1

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

Curator comments

IC50 = 0.063 microM

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

1. Bobadilla L RA, Perez-Alvarez V, Bracho Valdes I, Lopez-Sanchez P: Effect of pregnancy on the roles of nitric oxide and prostaglandins in 5-hydroxytryptamine-induced contractions in rat isolated thoracic and abdominal aorta. Clin Exp Pharmacol Physiol. 2005 Mar;32(3):202-9. [Article]
2. Fornai M, Blandizzi C, Colucci R, Antonioli L, Bernardini N, Segnani C, Baragatti B, Barogi S, Berti P, Spisni R, Del Tacca M: Role of cyclooxygenases 1 and 2 in the modulation of neuromuscular functions in the distal colon of humans and mice. Gut. 2005 May;54(5):608-16. [Article]
3. Higuchi K, Tominaga K, Watanabe T, Uno H, Shiba M, Sasaki E, Tanigawa T, Takashima T, Hamaguchi M, Oshitani N, Matsumoto T, Iwanaga Y, Fukuda T, Fujiwara Y, Arakawa T: Indomethacin, but not Helicobacter pylori, inhibits adaptive relaxation in isolated guinea-pig stomach. Drugs Exp Clin Res. 2004;30(5-6):235-41. [Article]
4. Kundu N, Walser TC, Ma X, Fulton AM: Cyclooxygenase inhibitors modulate NK activities that control metastatic disease. Cancer Immunol Immunother. 2005 Oct;54(10):981-7. Epub 2005 May 13. [Article]
5. Moth CW, Prusakiewicz JJ, Marnett LJ, Lybrand TP: Stereoselective binding of indomethacin ethanolamide derivatives to cyclooxygenase-1. J Med Chem. 2005 May 19;48(10):3613-20. [Article]
6. Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [Article]

Details4. Prostaglandin reductase 2

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

General Function

15-oxoprostaglandin 13-oxidase activity

Specific Function

Functions as 15-oxo-prostaglandin 13-reductase and acts on 15-keto-PGE1, 15-keto-PGE2, 15-keto-PGE1-alpha and 15-keto-PGE2-alpha with highest activity towards 15-keto-PGE2. Overexpression represses...

Gene Name

PTGR2

Uniprot ID

Q8N8N7

Uniprot Name

Prostaglandin reductase 2

Molecular Weight

38498.74 Da

References

1. Wu YH, Ko TP, Guo RT, Hu SM, Chuang LM, Wang AH: Structural basis for catalytic and inhibitory mechanisms of human prostaglandin reductase PTGR2. Structure. 2008 Nov 12;16(11):1714-23. doi: 10.1016/j.str.2008.09.007. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	50000	N/A	N/A	A27772

Details

Binding Properties5. Peroxisome proliferator-activated receptor gamma

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Activator

General Function

Zinc ion binding

Specific Function

Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...

Gene Name

PPARG

Uniprot ID

P37231

Uniprot Name

Peroxisome proliferator-activated receptor gamma

Molecular Weight

57619.58 Da

References

1. Cho MC, Lee HS, Kim JH, Choe YK, Hong JT, Paik SG, Yoon DY: A simple ELISA for screening ligands of peroxisome proliferator-activated receptor-gamma. J Biochem Mol Biol. 2003 Mar 31;36(2):207-13. [Article]
2. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA: Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1997 Feb 7;272(6):3406-10. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	24000	N/A	N/A	A27820
Ki (nM)	18100	N/A	N/A	A27820
Ki (nM)	24400	N/A	N/A	A27821

Details

Binding Properties6. Lactoylglutathione lyase

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

General Function

Zinc ion binding

Specific Function

Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione. Involved in the regulation of TNF-induced transcriptional activity of NF-kappa-B. Requ...

Gene Name

GLO1

Uniprot ID

Q04760

Uniprot Name

Lactoylglutathione lyase

Molecular Weight

20777.515 Da

References

1. Sato S, Kwon Y, Kamisuki S, Srivastava N, Mao Q, Kawazoe Y, Uesugi M: Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin. J Am Chem Soc. 2007 Jan 31;129(4):873-80. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	389	N/A	N/A	A27822

Details

Binding Properties7. Prostaglandin D2 receptor 2

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Other/unknown

General Function

Prostaglandin j receptor activity

Specific Function

Receptor for prostaglandin D2 (PGD2). Coupled to the G(i)-protein. Receptor activation may result in pertussis toxin-sensitive decreases in cAMP levels and Ca(2+) mobilization. PI3K signaling is al...

Gene Name

PTGDR2

Uniprot ID

Q9Y5Y4

Uniprot Name

Prostaglandin D2 receptor 2

Molecular Weight

43267.15 Da

References

1. Hata AN, Lybrand TP, Breyer RM: Identification of determinants of ligand binding affinity and selectivity in the prostaglandin D2 receptor CRTH2. J Biol Chem. 2005 Sep 16;280(37):32442-51. Epub 2005 Jul 19. [Article]
2. Hata AN, Lybrand TP, Marnett LJ, Breyer RM: Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2. Mol Pharmacol. 2005 Mar;67(3):640-7. Epub 2004 Nov 24. [Article]
3. Mathiesen JM, Ulven T, Martini L, Gerlach LO, Heinemann A, Kostenis E: Identification of indole derivatives exclusively interfering with a G protein-independent signaling pathway of the prostaglandin D2 receptor CRTH2. Mol Pharmacol. 2005 Aug;68(2):393-402. Epub 2005 May 3. [Article]

Details8. Peroxisome proliferator-activated receptor alpha

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Agonist

General Function

Zinc ion binding

Specific Function

Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...

Gene Name

PPARA

Uniprot ID

Q07869

Uniprot Name

Peroxisome proliferator-activated receptor alpha

Molecular Weight

52224.595 Da

References

1. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA: Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1997 Feb 7;272(6):3406-10. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	4100	N/A	N/A	A27818
IC 50 (nM)	2300	N/A	N/A	A27819
IC 50 (nM)	730	N/A	N/A	A27819
IC 50 (nM)	100	N/A	N/A	A27771

Details

Binding Properties9. Aldo-keto reductase family 1 member C3

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

General Function

Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity

Specific Function

Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....

Gene Name

AKR1C3

Uniprot ID

P42330

Uniprot Name

Aldo-keto reductase family 1 member C3

Molecular Weight

36852.89 Da

References

1. Lovering AL, Ride JP, Bunce CM, Desmond JC, Cummings SM, White SA: Crystal structures of prostaglandin D(2) 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin. Cancer Res. 2004 Mar 1;64(5):1802-10. [Article]
2. Adeniji A, Uddin MJ, Zang T, Tamae D, Wangtrakuldee P, Marnett LJ, Penning TM: Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. J Med Chem. 2016 Aug 25;59(16):7431-44. doi: 10.1021/acs.jmedchem.6b00160. Epub 2016 Aug 12. [Article]

Details10. Interferon-induced, double-stranded RNA-activated protein kinase

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inducer

General Function

IFN-induced dsRNA-dependent serine/threonine-protein kinase which plays a key role in the innate immune response to viral infection and is also involved in the regulation of signal transduction, apoptosis, cell proliferation and differentiation. Exerts its antiviral activity on a wide range of DNA and RNA viruses including hepatitis C virus (HCV), hepatitis B virus (HBV), measles virus (MV) and herpes simplex virus 1 (HHV-1). Inhibits viral replication via phosphorylation of the alpha subunit of eukaryotic initiation factor 2 (EIF2S1), this phosphorylation impairs the recycling of EIF2S1 between successive rounds of initiation leading to inhibition of translation which eventually results in shutdown of cellular and viral protein synthesis. Also phosphorylates other substrates including p53/TP53, PPP2R5A, DHX9, ILF3, IRS1 and the HHV-1 viral protein US11. In addition to serine/threonine-protein kinase activity, also has tyrosine-protein kinase activity and phosphorylates CDK1 at 'Tyr-4' upon DNA damage, facilitating its ubiquitination and proteosomal degradation. Either as an adapter protein and/or via its kinase activity, can regulate various signaling pathways (p38 MAP kinase, NF-kappa-B and insulin signaling pathways) and transcription factors (JUN, STAT1, STAT3, IRF1, ATF3) involved in the expression of genes encoding proinflammatory cytokines and IFNs. Activates the NF-kappa-B pathway via interaction with IKBKB and TRAF family of proteins and activates the p38 MAP kinase pathway via interaction with MAP2K6. Can act as both a positive and negative regulator of the insulin signaling pathway (ISP). Negatively regulates ISP by inducing the inhibitory phosphorylation of insulin receptor substrate 1 (IRS1) at 'Ser-312' and positively regulates ISP via phosphorylation of PPP2R5A which activates FOXO1, which in turn up-regulates the expression of insulin receptor substrate 2 (IRS2). Can regulate NLRP3 inflammasome assembly and the activation of NLRP3, NLRP1, AIM2 and NLRC4 inflammasomes. Can trigger apoptosis via FADD-mediated activation of CASP8. Plays a role in the regulation of the cytoskeleton by binding to gelsolin (GSN), sequestering the protein in an inactive conformation away from actin.

Specific Function

Atp binding

Gene Name

EIF2AK2

Uniprot ID

P19525

Uniprot Name

Interferon-induced, double-stranded RNA-activated protein kinase

Molecular Weight

62093.71 Da

References

1. Brunelli C, Amici C, Angelini M, Fracassi C, Belardo G, Santoro MG: The non-steroidal anti-inflammatory drug indomethacin activates the eIF2alpha kinase PKR, causing a translational block in human colorectal cancer cells. Biochem J. 2012 Apr 15;443(2):379-86. doi: 10.1042/BJ20111236. [Article]
2. Amici C, La Frazia S, Brunelli C, Balsamo M, Angelini M, Santoro MG: Inhibition of viral protein translation by indomethacin in vesicular stomatitis virus infection: role of eIF2alpha kinase PKR. Cell Microbiol. 2015 Sep;17(9):1391-404. doi: 10.1111/cmi.12446. Epub 2015 May 13. [Article]

Details11. Human Cyclooxygenases (Protein Group)

Kind

Protein group

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...

---

Components:

Name	UniProt ID
Prostaglandin G/H synthase 1	P23219
Prostaglandin G/H synthase 2	P35354

References

1. Raddino R, Pela G, Manca C, Barbagallo M, D'Aloia A, Passeri M, Visioli O: Mechanism of action of human calcitonin gene-related peptide in rabbit heart and in human mammary arteries. J Cardiovasc Pharmacol. 1997 Apr;29(4):463-70. doi: 10.1097/00005344-199704000-00006. [Article]
2. Camras CB, Miranda OC: The putative role of prostaglandins in surgical miosis. Prog Clin Biol Res. 1989;312:197-210. [Article]
3. Usami M, Kishimoto K, Ohata A, Miyoshi M, Aoyama M, Fueda Y, Kotani J: Butyrate and trichostatin A attenuate nuclear factor kappaB activation and tumor necrosis factor alpha secretion and increase prostaglandin E2 secretion in human peripheral blood mononuclear cells. Nutr Res. 2008 May;28(5):321-8. doi: 10.1016/j.nutres.2008.02.012. [Article]
4. Emerit I, Levy A, Cerutti P: Suppression of tumor promoter phorbolmyristate acetate-induced chromosome breakage by antioxidants and inhibitors of arachidonic acid metabolism. Mutat Res. 1983 Aug;110(2):327-35. doi: 10.1016/0027-5107(83)90149-5. [Article]

×

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