Identification
- Summary
Diphenhydramine is a H1 receptor antihistamine used in the treatment of seasonal allergies, and various allergic reactions including sneezing, runny nose, itchy/watery eyes, itching of nose or throat, pruritus, urticaria, insect bites/stings, and allergic rashes.
- Brand Names
- Acetadryl, Advil PM, Aleve PM, Allegra Cooling Relief Anti-itch, Banophen, Benadryl, Benadryl Itch Stopping, Benadryl-D Allergy and Sinus, Calagel, Damylin With Codeine, Dimetapp Nighttime Cold & Congestion, Diphen, Diphenhist, Diphenist, Excedrin PM Triple Action, Goody's PM, Legatrin PM, Motrin PM, Nytol, Nytol Quickgels, Percogesic Reformulated Jan 2011, Siladryl, Simply Sleep, Sleepinal, Sominex, Triaminic Night Time Cold & Cough, Tylenol PM, Unisom, Unisom Sleep, Vanamine, Wal-dryl, Wal-som (doxylamine), Zzzquil
- Generic Name
- Diphenhydramine
- DrugBank Accession Number
- DB01075
- Background
Diphenhydramine - perhaps known most commonly as its brand name formulation Benadryl - is a first-generation H1 receptor antihistamine that is used extensively for the treatment of seasonal allergies, insect bites and stings, and rashes 9,10,11,17. However, it also has antiemetic, antitussive, hypnotic, and antiparkinson properties 11,16. As histamine receptors exist both peripherally and in the central nervous system, diphenhydramine has been shown to cause sedation due to its competitive antagonism of histamine H1 receptors within the central nervous system 9,10,11,17,5. While its use in allergy therapy can sometimes fall out of favor due to its sedative effect, diphenhydramine has been repurposed for use within many non-prescription over-the-counter sleep aids and cough-and-cold medications that have been marketed for "night time" use 9,12,13.
Diphenhydramine is also used in combination with 8-chlorotheophylline as the anti-nausea drug Dimenhydrinate where it is utilized primarily for its antagonism of H1 histamine receptors within the vestibular system 4.
Diphenhydramine has also been shown to be implicated in a number of neurotransmitter systems that affect behaviour including dopamine, norepinephrine, serotonin, acetylcholine, and opioid 3. As a result, diphenhydramine is being investigated for its anxiolytic and anti-depressant properties.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Diphenhydramine (DB01075)
- Weight
- Average: 255.3547
Monoisotopic: 255.162314299 - Chemical Formula
- C17H21NO
- Synonyms
- 2-(benzhydryloxy)-N,N-dimethylethylamine
- 2-diphenylmethoxy-N,N-demthylethanamine
- Difenhidramina
- Diphenhydramine
- Diphenhydraminum
- N-(2-(diphenylmethoxy)ethyl)-N,N-dimethylamine
- O-benzhydryldimethylaminoethanol
- α-(2-dimethylaminoethoxy)diphenylmethane
- β-dimethylaminoethanol diphenylmethyl ether
- β-dimethylaminoethyl benzhydryl ether
Pharmacology
- Indication
Diphenhydramine is a first-generation histamine H1 receptor antagonist (H1 antihistamine) that is widely available as a non-prescription, over-the-counter (OTC) medication. As an OTC medication, diphenhydramine is typically formulated as tablets and creams indicated for use in treating sneezing, runny nose, itchy/watery eyes, itching of nose or throat, insomnia, pruritis, urticaria, insect bites/stings, allergic rashes, and nausea 9,10,11,17,5.
Additionally, when the use of oral diphenhydramine is impractical, there are also prescription-only formulations such as diphenhydramine injection products that are effective in adults and pediatric patients (other than premature infants and neonates) for: i) the amelioration of allergic reactions to blood or plasma, in anaphylaxis as an adjunct to epinephrine and other standard measures after acute allergic reaction symptoms have been controlled, and for other uncomplicated allergic conditions of the immediate type when oral therapy is impossible or contraindicated 16; ii) the active treatment of motion sickness 16; and iii) use in parkinsonism when oral therapy is impossible or contraindicated, as follows: parkinsonism in the elderly who are unable to tolerate more potent agents; mild cases of parkinsonism in other age groups, and in other cases of parkinsonism in combination with centrally acting anticholinergic agents 16.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Allergic rhinitis •••••••••••• ••••••••• Used in combination to treat Allergic cough Combination Product in combination with: Guaifenesin (DB00874), Bromhexine (DB09019) •••••••••••• •••••••• Used in combination to treat Allergic cough Combination Product in combination with: Sodium citrate (DB09154), Guaifenesin (DB00874) •••••••••••• •••••••• Used in combination for symptomatic treatment of Allergies Combination Product in combination with: Acetaminophen (DB00316), Pseudoephedrine (DB00852) •••••••••••• Symptomatic treatment of Allergies •••••••••••• ••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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Diphenhydramine has anti-histaminic (H1-receptor), anti-emetic, anti-vertigo and sedative and hypnotic properties 12. The anti-histamine action occurs by blocking the spasmogenic and congestive effects of histamine by competing with histamine for H1 receptor sites on effector cells, preventing but not reversing responses mediated by histamine alone 12. Such receptor sites may be found in the gut, uterus, large blood vessels, bronchial muscles, and elsewhere 12. Anti-emetic action is by inhibition at the medullary chemoreceptor trigger zone 12. Anti-vertigo action is by a central antimuscarinic effect on the vestibular apparatus and the integrative vomiting center and medullary chemoreceptor trigger zone of the midbrain 12.
- Mechanism of action
Diphenhydramine predominantly works via the antagonism of H1 (Histamine 1) receptors 9,10,11,17,5. Such H1 receptors are located on respiratory smooth muscles, vascular endothelial cells, the gastrointestinal tract (GIT), cardiac tissue, immune cells, the uterus, and the central nervous system (CNS) neurons 9,10,11,17,5. When the H1 receptor is stimulated in these tissues it produces a variety of actions including increased vascular permeability, promotion of vasodilation causing flushing, decreased atrioventricular (AV) node conduction time, stimulation of sensory nerves of airways producing coughing, smooth muscle contraction of bronchi and the GIT, and eosinophilic chemotaxis that promotes the allergic immune response 9,10,11,17,5.
Ultimately, diphenhydramine functions as an inverse agonist at H1 receptors, and subsequently reverses effects of histamine on capillaries, reducing allergic reaction symptoms 9,10,11,17,5. Moreover, since diphenhydramine is a first-generation antihistamine, it readily crosses the blood-brain barrier and inversely agonizes the H1 CNS receptors, resulting in drowsiness, and suppressing the medullary cough center 9,10,11,17,5.
Furthermore, H1 receptors are similar to muscarinic receptors 9,10,11,17,5. Consequently, diphenhydramine also acts as an antimuscarinic 9,10,11,17,5. It does so by behaving as a competitive antagonist of muscarinic acetylcholine receptors, resulting in its use as an antiparkinson medication 9,10,11,17,5.
Lastly, diphenhydramine has also demonstrated activity as an intracellular sodium channel blocker, resulting in possible local anesthetic properties 9.
Target Actions Organism AHistamine H1 receptor antagonistHumans UMuscarinic acetylcholine receptor M2 antagonistHumans - Absorption
Diphenhydramine is quickly absorbed after oral administration with maximum activity occurring in approximately one hour 6,13. The oral bioavailability of diphenhydramine has been documented in the range of 40% to 60%, and peak plasma concentration occurs about 2 to 3 hours after administration 6,13.
- Volume of distribution
Diphenhydramine is widely distributed throughout the body, including the CNS 18. Following a 50 mg oral dose of diphenhydramine, the volume of distribution is in the range of 3.3 - 6.8 l/kg 18.
- Protein binding
Some prescribing information records the protein binding of diphenhydramine as approximately 78% 18 while others have suggested the medication is about 80 to 85% 13 bound to plasma proteins.
- Metabolism
Diphenhydramine undergoes rapid and extensive first-pass metabolism 18,13,8. In particular, two successive N-demethylations occur wherein diphenhydramine is demethylated to N-desmethyldiphenhydramine (the N-desmethyl metabolite) and then this metabolite is itself demethylated to N,N-didesmethyldiphenhydramine (the N,N-didesmethyl metabolite) 18,8. Subsequently, acetyl metabolites like N-acetyl-N-desmethyldiphenhydramine are generated via the amine moiety of the N,N-didesmethyl metabolite 8. Additionally, the N,N-didesmethyl metabolite also undergoes some oxidation to generate the diphenylmethoxyacetic acid metabolite as well 18,13,8. The remaining percentage of a dose of administered diphenhydramine is excreted unchanged 18,13,8. The metabolites are further conjugated with glycine and glutamine and excreted in urine 13.
Moreover, studies have determined that a variety of cytochrome P450 isoenzymes are involved in the N-demethylation that characterizes the primary metabolic pathway of diphenhydramine, including CYP2D6, CYP1A2, CYP2C9, and CYP2C19 7. In particular, CYP2D6 demonstrates higher affinity catalysis with the diphenhydramine substrate than the other isoenzymes identified 7. Consequently, inducers or inhibitors of these such CYP enzymes may potentially affect the serum concentration and incidence and/or severity of adverse effects associated with exposure to diphenhydramine 7.
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- Route of elimination
The metabolites of diphenhydramine are conjugated with glycine and glutamine and excreted in urine 12,13. Only about 1% of a single dose is excreted unchanged in urine 12,13. The medication is ultimately eliminated by the kidneys slowly, mainly as inactive metabolites 12,13.
- Half-life
The elimination half-life ranges from 2.4-9.3 hours in healthy adults 18,13. The terminal elimination half-life is prolonged in liver cirrhosis 13.
- Clearance
Values for plasma clearance of a 50 mg oral dose of diphenhydramine has been documented as lying in the range of 600-1300 ml/min 18.
- Adverse Effects
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Overdose is expected to result in effects similar to the adverse effects that are ordinarily associated with the use of diphenhydramine, including drowsiness, hyperpyrexia, and anticholinergic effects, among others 10,11,12,13,18. Additional symptoms during overdose may include mydriasis, fever, flushing, agitation, tremor, dystonic reactions, hallucinations and ECG changes 13. Large overdose may cause rhabdomyolysis, convulsions, delirium, toxic psychosis, arrhythmias, coma and cardiovascular collapse 13. Moreover, with higher doses, and particularly in children, symptoms of CNS excitation including hallucinations and convulsions may appear; with massive doses, coma or cardiovascular collapse may follow 18.
Although diphenhydramine has been in widespread use for many years without ill consequence, it is known to cross the placenta and has been detected in breast milk 18. This medication should therefore only be used when the potential benefit of treatment to the mother exceeds any possible hazards to the developing fetus or suckling infant 18.
Pharmacokinetic studies indicate no major differences in the distribution or elimination of diphenhydramine compared to younger adults 18. Nevertheless, diphenhydramine should be used with caution in the elderly, who are more likely to experience adverse effects 13. Avoid use in elderly patients with confusion 13.
The results of a review on the use of diphenhydramine in renal failure suggest that in moderate to severe renal failure, the dose interval should be extended by a period dependent on Glomerular filtration rate (GFR) 18.
After intravenous administration of 0.8 mg/kg diphenhydramine, a prolonged half-life was noted in patients with chronic liver disease which correlated with the severity of the disease 18. However, the mean plasma clearance and apparent volume of distribution were not significantly affected 18.
LD50=500 mg/kg (orally in rats). Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular dysrhythmias, coma and death.
- Pathways
Pathway Category Diphenhydramine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Diphenhydramine is combined with 1,2-Benzodiazepine. Abatacept The metabolism of Diphenhydramine can be increased when combined with Abatacept. Abemaciclib The risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Diphenhydramine. Abiraterone The metabolism of Diphenhydramine can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Diphenhydramine. - Food Interactions
- Avoid alcohol.
- Take before a meal. Take 30 minutes before a meal or 30 minutes before departure for motion sickness.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Diphenhydramine citrate 4OD433S209 88637-37-0 SPCKHVPPRJWQRZ-UHFFFAOYSA-N Diphenhydramine hydrochloride TC2D6JAD40 147-24-0 PCHPORCSPXIHLZ-UHFFFAOYSA-N Diphenhydramine methylbromide UJO67AO8YI 31065-89-1 BDQPXVWYFLTETB-UHFFFAOYSA-M Diphenhydramine salicylate 707L3YC54L 7491-10-3 RTSZUSOHOIFYSY-UHFFFAOYSA-N - Active Moieties
Name Kind UNII CAS InChI Key Phenol unknown 339NCG44TV 108-95-2 ISWSIDIOOBJBQZ-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Aleryl / Alledryl / Allerdryl (Valeant) / Belix / Benylan (Biogen) / Dermodrin (Montavit) / Desentol (Meda) / Dibondrin (Montavit) / Dimedrol (Zdorovie) / Diphen (Wockhardt) / Dormarex 2 / Genahist / Histaxin (Meda) / Hyrexin (Hyrex) / Nytol Quickgels (GlaxoSmithKline) / Restamin (Kowa Souyaku) / Siladryl / Silphen Cough
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Benadryl Injection, solution 50 mg/1mL Intramuscular; Intravenous Parke Davis Div Of Pfizer Inc 1947-03-06 2008-01-31 US 
Benadryl Injection, solution 50 mg/1mL Intramuscular; Intravenous Physicians Total Care, Inc. 1994-06-01 2010-12-29 US Benadryl Injection, solution 50 mg/1mL Intramuscular; Intravenous Parke Davis Div Of Pfizer Inc 1957-12-30 2007-01-31 US Benadryl Injection, solution 50 mg/1mL Intramuscular; Intravenous Physicians Total Care, Inc. 2006-01-13 2010-12-29 US Benadryl Inj. 50mg/ml Liquid 50 mg / mL Intramuscular; Intravenous Warner Lambert Canada Inc. 1994-12-31 2000-11-27 Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Di-phen Solution 12.5 mg/5mL Oral TriVue Pharmaceuticals, Inc. 2020-10-02 2022-03-31 US Diphen Solution 12.5 mg/5mL Oral Foxland Pharmaceuticals, Inc. 2019-09-11 Not applicable US Diphendydramine Hydrochloride Capsule 25 mg/1 Oral Remedy Repack 2010-12-17 2017-04-24 US 
Diphenhydramine Injection, solution 50 mg/1mL Intramuscular; Intravenous REMEDYREPACK INC. 2023-03-20 Not applicable US Diphenhydramine Injection, solution 50 mg/1mL Intramuscular; Intravenous Micro Labs Limited 2019-12-10 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 24/7 Life Allergy Relief Tablet, film coated 25 mg/1 Oral Lil' Drug Store Products, Inc. 2020-12-12 Not applicable US 7 Select Allergy Tablet 25 mg/1 Oral 7-Eleven 2014-04-22 2021-02-28 US 7 Select Allergy Childrens Solution 12.5 mg/5mL Oral 7-Eleven 2014-08-05 2021-04-30 US 7 Select Night Time Sleep Aid Solution 50 mg/30mL Oral 7-Eleven 2014-04-22 2021-05-31 US A Health Itch Relief Gel Gel 2 mg/100mL Topical Bionpharma, Inc. 2022-11-08 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 24 / 7 Life Extra Strength Pain Reliever PM Diphenhydramine hydrochloride (25 mg/1) + Acetaminophen (500 mg/1) Tablet, film coated Oral Lil' Drug Store Products, Inc. 2020-12-17 Not applicable US 7 Select Ibuprofen PM Diphenhydramine citrate (38 mg/1) + Ibuprofen (200 mg/1) Tablet, film coated Oral 7-Eleven 2014-08-05 2020-11-30 US 7 Select Night Time Severe Cold Cough and Flu Diphenhydramine hydrochloride (25 mg/1) + Acetaminophen (650 mg/1) + Phenylephrine hydrochloride (10 mg/1) Powder, for solution Oral 7-Eleven 2016-01-25 2021-01-01 US 7 Select Night Time severe cold, cough and flu Diphenhydramine hydrochloride (25 mg/1) + Acetaminophen (650 mg/1) + Phenylephrine hydrochloride (10 mg/1) Powder, for solution Oral 7 Eleven 2015-11-12 2017-08-01 US 7 Select Pain Relief PM Diphenhydramine hydrochloride (25 mg/1) + Acetaminophen (500 mg/1) Tablet, film coated Oral 7 Eleven 2014-09-04 2016-07-22 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Airacof Diphenhydramine hydrochloride (12.5 mg/5mL) + Codeine phosphate hemihydrate (7.5 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL) Liquid Oral Centurion Labs 2010-01-08 2016-05-02 US Antiphlamine Coin Plaster Diphenhydramine (0.246 mg/0.2832g) + Levomenthol (2.769 mg/0.2832g) + Synthetic camphor (1.108 mg/0.2832g) Patch Topical Hanul Trading Co., Ltd. 2016-10-10 2017-04-14 US Antiphlamine Coin Plaster Diphenhydramine (0.246 mg/0.2832g) + DL-alpha-Tocopherol (0.308 mg/0.2832g) + Levomenthol (2.769 mg/0.2832g) + Methyl salicylate (5.541 mg/0.2832g) + Nonivamide (0.046 mg/0.2832g) + Peppermint oil (0.693 mg/0.2832g) + Synthetic camphor (1.108 mg/0.2832g) Patch Topical Hanul Trading Co., Ltd. 2016-10-10 Not applicable US Basic Dental Emergency Kit Diphenhydramine hydrochloride (50 mg/1mL) + Acetylsalicylic acid (325 mg/1) + D-glucose (4000 mg/1) + Epinephrine (0.3 mg/0.3mL) + Nitroglycerin (0.4 mg/1) + Salbutamol sulfate (108 ug/1) Aerosol, metered; Injection; Kit; Tablet; Tablet, chewable Intramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual Best Dental Kit LLC 2023-01-30 Not applicable US Benadryl Diphenhydramine hydrochloride (50 mg/1mL) Injection, solution Intramuscular; Intravenous Physicians Total Care, Inc. 1994-06-01 2010-12-29 US
Categories
- ATC Codes
- D04AA32 — Diphenhydramine
- D04AA — Antihistamines for topical use
- D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D — DERMATOLOGICALS
- R06AA — Aminoalkyl ethers
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- D04AA — Antihistamines for topical use
- D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D — DERMATOLOGICALS
- Drug Categories
- Agents producing tachycardia
- Amines
- Aminoalkyl Ethers
- Anesthetics
- Anesthetics, Local
- Anti-Allergic Agents
- Anticholinergic Agents
- Antiemetics
- Antihistamines for Systemic Use
- Antihistamines for Topical Use
- Antipruritics, Incl. Antihistamines, Anesthetics, Etc.
- Benzene Derivatives
- Benzhydryl Compounds
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Drugs causing inadvertant photosensitivity
- Ethanolamine Derivatives
- Ethylamines
- First Generation Antihistamines
- Gastrointestinal Agents
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Hypnotics and Sedatives
- Muscarinic Antagonists
- OCT2 Inhibitors
- Photosensitizing Agents
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Sleep Aids, Pharmaceutical
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Benzylethers / Trialkylamines / Dialkyl ethers / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aromatic homomonocyclic compound / Benzylether / Dialkyl ether / Diphenylmethane / Ether / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- tertiary amino compound, ether (CHEBI:4636) / a small molecule (CPD-10890)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 8GTS82S83M
- CAS number
- 58-73-1
- InChI Key
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3
- IUPAC Name
- [2-(diphenylmethoxy)ethyl]dimethylamine
- SMILES
- CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
References
- Synthesis Reference
Alison B. Lukacsko, Joseph J. Piala, "Effect of a combination of a terbutaline, diphenhydramine and ranitidine composition on gastrointestinal injury produced by nonsteroidal anti-inflammatory compositions." U.S. Patent US5260333, issued December, 1983.
US5260333- General References
- Raphael GD, Angello JT, Wu MM, Druce HM: Efficacy of diphenhydramine vs desloratadine and placebo in patients with moderate-to-severe seasonal allergic rhinitis. Ann Allergy Asthma Immunol. 2006 Apr;96(4):606-14. [Article]
- Abdi A, Rose E, Levine M: Diphenhydramine overdose with intraventricular conduction delay treated with hypertonic sodium bicarbonate and i.v. lipid emulsion. West J Emerg Med. 2014 Nov;15(7):855-8. doi: 10.5811/westjem.2014.8.23407. Epub 2014 Sep 19. [Article]
- Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [Article]
- Jaju BP, Wang SC: Effects of diphenhydramine and dimenhydrinate on vestibular neuronal activity of cat: a search for the locus of their antimotion sickness action. J Pharmacol Exp Ther. 1971 Mar;176(3):718-24. [Article]
- Flake ZA, Scalley RD, Bailey AG: Practical selection of antiemetics. Am Fam Physician. 2004 Mar 1;69(5):1169-74. [Article]
- Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [Article]
- Akutsu T, Kobayashi K, Sakurada K, Ikegaya H, Furihata T, Chiba K: Identification of human cytochrome p450 isozymes involved in diphenhydramine N-demethylation. Drug Metab Dispos. 2007 Jan;35(1):72-8. doi: 10.1124/dmd.106.012088. Epub 2006 Oct 4. [Article]
- Rodrigues WC, Castro C, Catbagan P, Moore C, Wang G: Immunoassay screening of diphenhydramine (Benadryl(R)) in urine and blood using a newly developed assay. J Anal Toxicol. 2012 Mar;36(2):123-9. doi: 10.1093/jat/bkr015. [Article]
- StatPearls [Internet]: Diphenhydramine [Link]
- Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Tablets Patient Information [Link]
- Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Cream Monograph [Link]
- Electronic Medicines Compendium: Boots Sleepeaze (diphenhydramine hydrochloride) 50mg Tablets Monograph [Link]
- Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph [Link]
- DailyMed: Ibuprofen PM (ibuprofen/diphenhydramine) product information [Link]
- BASG Product Information: Multodrin (dexamethasone/diphenhydramine hydrochloride) topical ointment [Link]
- Diphenhydramine Hydrochloride Injection, USP FDA Label [File]
- DIPHENHYDRAMINE- diphenhydramine hcl tablet, coated DailyMed FDA Label [File]
- Benylin Chesty Coughs UK MHRA Product Information [File]
- External Links
- Human Metabolome Database
- HMDB0001927
- KEGG Drug
- D00300
- KEGG Compound
- C06960
- PubChem Compound
- 3100
- PubChem Substance
- 46505484
- ChemSpider
- 2989
- BindingDB
- 50017674
- 3498
- ChEBI
- 4636
- ChEMBL
- CHEMBL657
- ZINC
- ZINC000000020244
- Therapeutic Targets Database
- DAP000490
- PharmGKB
- PA449349
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- 2PM
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Diphenhydramine
- PDB Entries
- 2aot / 8et7
- MSDS
- Download (73.5 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 Diagnostic Asthma 1 4 Completed Prevention Cystoid Macular Edema Following Cataract Surgery, Bilateral 1 4 Completed Prevention Hypnotics / Specified Sedative 1 4 Completed Prevention Neurogenic Bladder / Overactive Bladder Syndrome (OABS) / Painful Bladder Syndrome (PBS) / Urinary Urge Incontinence 1 4 Completed Prevention Ocular Hypertension / Posterior Capsule Opacification 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Advance Pharmaceutical
- Advent Pharmaceuticals Inc.
- Amend
- APP Pharmaceuticals
- A-S Medication Solutions LLC
- Auriga Pharmaceuticals LLC
- Barr Pharmaceuticals
- Baxter International Inc.
- Bergen Brunswig
- Bioniche Pharma
- Bryant Ranch Prepack
- C.O. Truxton Inc.
- Cardinal Health
- Carlisle Laboratories Inc.
- Chattem Chemicals Inc.
- Concord Labs
- Consolidated Midland Corp.
- Contract Pharm
- CVS Pharmacy
- Darby Dental Supply Co. Inc.
- Dept Health Central Pharmacy
- Direct Dispensing Inc.
- DispenseXpress Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Eon Labs
- Equaline Vitamins
- Fusion Pharmaceuticals LLC
- General Injectables and Vaccines Inc.
- GlaxoSmithKline Inc.
- Goldline Laboratories Inc.
- Group Health Cooperative
- Hawthorn Pharmaceuticals
- Heartland Repack Services LLC
- Hospira Inc.
- Innoviant Pharmacy Inc.
- Ivax Pharmaceuticals
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- Dosage Forms
Form Route Strength Tablet, effervescent Oral Capsule Tablet Not applicable Kit; tablet Oral Kit Topical Capsule; kit Oral Cream Topical 20 mg/1mL Cream Topical 2.0 mL/100mL Granule, effervescent Oral 25 MG Injection, solution Intravenous 20 mg/2ml Elixir Oral 12.5 mg / 5 mL Cream Topical Liquid Oral 12.5 mg/5mL Capsule, gelatin coated Oral Capsule Oral Powder Oral 25 mg/1 Bar, chewable Oral 25 mg/1 Syrup Oral 10 mg/4mL Solution Oral 12.5 mg / 5 mL Gel Topical 2 g/100g Cream Topical 2.0 % Patch Topical Aerosol, metered; injection; kit; tablet; tablet, chewable Intramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual Solution Oral 0.12 g/5ml Capsule Oral Injection, solution Intramuscular; Intravenous 50 mg/1mL Kit; tablet, film coated Oral Syrup Oral 0.2500 g Tablet Oral 25.00 mg Tablet, coated Oral 25 mg/1 Strip Oral 25 mg/1 Syrup Oral 125 mg/5ml Cream Topical 2 % Solution Topical Gel Topical 20 mg/1mL Tablet, chewable Oral 25 mg Gel Topical 2 % Solution Parenteral 50 mg Tablet Oral 25 mg/250mg Oil Oral 50 mg/10mL Solution Intramuscular; Intravenous 20 mg Capsule, gelatin coated Oral 25 mg Strip Oral 25 mg Liquid Oral 12.5 mg / 5 mL Syrup Oral 250.000 mg Lotion Topical Syrup Oral 250.00 mg Suspension Topical Tablet, sugar coated Oral 50 mg Gel Urethral Syrup Oral 6.25 mg / 5 mL Tablet, orally disintegrating Oral 12.5 mg Tablet, chewable Oral 12.5 mg Tablet Oral 19 mg Solution Oral 6.25 mg / 5 mL Strip Oral 19 mg Tablet Oral 12.5 mg/1 Tablet, chewable Oral 12.5 mg/1 Kit; solution Oral Liquid Oral 6.25 mg/1mL Suspension Oral Liquid Oral 6.25 mg / 5 mL Solution / drops Ophthalmic Solution / drops; suspension / drops Nasal Powder Not applicable Gel; kit; lipstick; liquid; lotion; swab Topical Ointment Topical Spray Topical Kit; liquid Oral Aerosol, metered; injection; kit; solution; tablet; tablet, chewable Intramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual Liquid Topical Ointment Topical 20 mg/g Injection, solution Intramuscular; Intravenous 30 mg Solution Oral 2 mg/ml Kit Oral 0.75 g/0.75g Kit Oral 0.86 g/0.86g Solution Parenteral 100.000 mg Solution Parenteral 10.000 mg Capsule, coated Oral 5000000 mg Capsule, coated Oral 50 mg Syrup Oral 250 mg Solution Intramuscular; Intravenous 10 mg Syrup Oral 0.25 g Syrup Oral Tablet Oral 38.0 mg Elixir; kit; solution Oral Cream; kit; liquid; ointment; tablet; tablet, chewable; tablet, film coated Oral; Topical Tablet Oral Capsule, coated Oral 25 mg/1 Injection, solution Intravenous 50 mg/1mL Tablet, coated Oral 25 mg/ 11 Solution Oral 62.5 mg/5ml Capsule, liquid filled Oral 20 mg/1 Injection Tablet Oral 50 mg/1 Tablet, film coated Oral 25 mg/25mg Capsule, gelatin coated Oral 25 mg/1 Liquid Intravenous 50 mg / mL Capsule Oral 25 mg/1 Capsule Oral 50 mg/1 Capsule, liquid filled Oral 50 mg/1 Injection Intramuscular 50 mg/1mL Injection Intramuscular; Intravenous 50 mg/1mL Injection Parenteral 50 mg/1mL Liquid Oral 2.5 mg/1mL Solution Oral 25 mg/10mL Solution Oral 50 mg/20mL Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Tablet, orally disintegrating Oral 25 mg/1 Liquid Intramuscular; Intravenous 50 mg / mL Tablet, chewable Oral Elixir Oral Syrup Oral Solution Oral 50 mg/30mL Gel Topical 2 mg/100mL Tablet Oral 10 mg Capsule, liquid filled Oral 25 mg/1 Cream Topical 50 g Solution Oral 50 mg/40mL Kit Oral Bar, chewable Oral 12.5 mg/1 Capsule Oral 25.000 mg Aerosol, spray Topical Powder Oral Tablet Oral 25 mg/1 Tablet Oral 50.000 mg Syrup Oral 135 mg/5ml Syrup Oral 14 mg/5ml Capsule, liquid filled Oral Solution Intravenous 100.000 mg Tablet, chewable Oral; Topical Liquid Topical 20.3 g/1L Spray Topical 2 g/100mL Cream Topical 2 % w/w Gel Topical 2.03 g/100g Aerosol Topical Strip Oral 12.5 mg Cream; kit; tablet, film coated Oral; Topical Tablet Oral 12.5 mg Syrup Lotion Topical 100 ml Tablet, orally disintegrating Oral 12.5 mg/1 Liniment Topical Tablet Spray Nasal Liquid Oral 50 mg/20mL Capsule, gelatin coated Oral 50 mg/1 Syrup Oral 14 mg Kit Oral; Topical Kit; solution; suspension Oral Tablet Oral 8 mg Kit; powder, for solution Oral Lozenge Oral 25 mg Strip Oral Solution Oral 12.5 mg/5ml Cream Liquid Oral 50 mg/30mL Solution Oral 50 mg / 30 mL Capsule, liquid filled Oral 50 mg/21 Solution Oral Capsule Oral 25.00000 mg Granule, for solution Oral Tablet, coated Oral Tablet, sugar coated Oral 25 mg Syrup Oral 100 ml Elixir Oral 2.5 mg / mL Cream Topical Granule Oral Solution Oral 12.5 mg/5mL Syrup Oral 12.5 mg/5mL Tablet Oral Tablet, coated Oral 50 mg Gel Topical 20.5 mg/1mL Liquid Oral Plaster Topical Solution Intramuscular; Intravenous 50 mg / mL Gel Topical 2 g/100mL Gel Topical .2 g/10mL Kit; tablet, coated Oral Tablet Oral 25 mg / tab Capsule Oral 50 mg / cap Tablet Oral 50 mg / tab Tablet, coated Oral 50 mg/1 Syrup Oral 102 mg/5ml Kit; tablet; tablet, film coated Oral Suspension Oral 62.5 mg/5ml Gel Topical Kit Topical 20 mg/1g Spray Topical 20 mg/1g Tablet, multilayer Oral Tablet, multilayer, extended release Oral Gel Topical 20 mg/1g Spray Topical 20 mg/1mL Capsule, coated Oral Gum, chewing Oral Gum, chewing Oral 20 MG Kit; powder; syrup Oral Tablet, film coated Oral Tablet, delayed release Oral Syrup Oral 135 mg/5ml Tablet, chewable Oral 25 mg/1 Powder, for solution Oral Tablet, film coated Oral Tablet, film coated Oral 25 MG Tablet, coated Oral 100 MG Liquid Oral 25 mg/10mL Capsule, gelatin coated Oral 50 mg/21 Kit; tablet, chewable Oral; Topical Spray Topical 2.0 % w/w Capsule Oral 25 MG Tablet Oral 0.05 G Tablet Oral 50 MG Capsule Oral 0.05 g Gum, chewing Oral 25 MG Spray Topical 2 mg/100mL Suspension Oral 135 mg/5ml Liquid Oral 50 mg / 30 mL Tablet Oral 25 mg Elixir Capsule Oral 50 mg Tablet, coated Oral 25 mg - Prices
Unit description Cost Unit DiphenhydrAMINE HCl 100 50 mg capsule Bottle 13.99USD bottle Diphenhydramine 50 mg/ml 3.94USD ml Diphenhydramine 50 mg/ml vial 1.69USD ml DiphenhydrAMINE HCl 50 mg/ml vial 1.44USD vial Dytan 25 mg tablet chewable 1.37USD tablet Benadryl 50 mg/ml vial 1.36USD ml Diphenmax 25 mg tablet 1.24USD tablet Benadryl allergy 25 mg strips 0.45USD strip Unisom sleep aid tablet 0.34USD tablet Sleep-eze 3 tablet 0.29USD tablet Compoz 50 mg tablet 0.27USD tablet Sominex max str 50 mg caplet 0.27USD caplet Benadryl allergy fastmelt tablet 0.26USD tablet Unisom 25 mg sleeptabs 0.25USD tablet Unisom 50 mg sleepgels 0.25USD each Unisom sleepmelts 25 mg tablet 0.24USD tablet Nytol 25 mg tablet 0.23USD tablet Benadryl allergy-sinus caplet 0.22USD caplet Compoz 25 mg gelcap 0.2USD capsule Benadryl allergy 25 mg softgel 0.19USD softgel capsule Benadryl allergy 25 mg ultratab 0.19USD tablet Benadryl allergy-cold kapgels 0.19USD each Benadryl allergy-sinus kapgels 0.19USD each Benadryl-d allergy-sinus ultratab 0.19USD tablet Diphenhydramine hcl powder 0.17USD g Eql allergy 25 mg tablet 0.17USD tablet Nighttime sleep aid 25 mg cplt 0.17USD caplet Banophen anti-itch 2% cream 0.16USD g Benadryl itch relief stick 0.16USD ml Sominex 25 mg tablet 0.16USD tablet Benadryl allergy 25 mg kapgels 0.15USD each Allergy 25 mg tablet 0.14USD tablet Benadryl 25 mg kapseals 0.14USD each Benadryl itch stopping crm 0.14USD g DiphenhydrAMINE HCl 25 mg capsule 0.13USD capsule Diphenhist with zinc cream 0.12USD g Ra allergy 25 mg tablet 0.12USD tablet CVS Pharmacy allergy 25 mg tablet 0.11USD tablet Diphenhydramine 25 mg minitab 0.11USD tablet Simply sleep 25 mg caplet 0.11USD caplet Sleep ii tablet 0.11USD tablet Diphenhydramine 50 mg capsule 0.1USD capsule Benadryl 2% spray 0.09USD ml Diphenhist 50 mg tablet 0.09USD tablet Genahist 25 mg tablet 0.09USD tablet Ra sleep tablet 0.09USD tablet Banophen 25 mg tablet 0.08USD tablet Wal-dryl anti-itch spray 0.08USD ml CVS Pharmacy allergy 25 mg caplet 0.07USD caplet Nighttime sleep aid 25 mg caplet 0.07USD caplet CVS Pharmacy itch relief spray 0.06USD ml Diphen 25 mg capsule 0.06USD capsule Diphenhist 25 mg caplet 0.06USD caplet Benadryl anti-itch 0.45% gel 0.05USD g Diphenhydramine 50 mg caplet 0.05USD caplet Benadryl itch stopping gel 0.04USD g Child benadryl-d aller-sin liquid 0.04USD ml Diphenhydramine 25 mg capsule 0.04USD capsule Vicks 44d cough & head liquid 0.03USD ml Vicks 44e cough & chest liquid 0.03USD ml Banophen allergy liquid 0.02USD ml Diphenhydramine 25 mg tablet 0.02USD tablet Ra anti-tussive dm syrup 0.02USD ml Siladryl 12.5 mg/5 ml liquid 0.02USD ml Silphen cough syrup 0.02USD ml Silphen dm cough syrup 0.02USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8883849 No 2014-11-11 2022-01-17 US US9155718 No 2015-10-13 2022-01-17 US US8263647 No 2012-09-11 2022-05-30 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 161-162 Martin, H., Hafliger, F.,Gatzi, K.and Grob, A.; U.S. Patent 2,397,799; April 2,1946; assigned to J.R. Geigy AG, Switzerland. Rieveschl, G. Jr.; U.S. Patent 2,421,714; June 3,1947; assigned to Parke, Davis & Co. Rieveschl, G. Jr.; U.S. Patent 2,427,878; September 23,1947; assigned to Parke, Davis & Company. boiling point (°C) 150-165 °C at 2.00E+00 mm Hg PhysProp water solubility 3060 mg/L (at 37 °C) BEILSTEIN logP 3.27 HANSCH,C ET AL. (1995) pKa 8.98 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0752 mg/mL ALOGPS logP 3.44 ALOGPS logP 3.65 Chemaxon logS -3.5 ALOGPS pKa (Strongest Basic) 8.87 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.47 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 79.93 m3·mol-1 Chemaxon Polarizability 29.86 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9898 Blood Brain Barrier + 0.9381 Caco-2 permeable + 0.8744 P-glycoprotein substrate Substrate 0.6211 P-glycoprotein inhibitor I Non-inhibitor 0.6632 P-glycoprotein inhibitor II Non-inhibitor 0.8381 Renal organic cation transporter Inhibitor 0.7752 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.6173 CYP450 1A2 substrate Inhibitor 0.8306 CYP450 2C9 inhibitor Non-inhibitor 0.9144 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9039 CYP450 3A4 inhibitor Non-inhibitor 0.934 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7293 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.6495 Biodegradation Not ready biodegradable 0.9253 Rat acute toxicity 2.7846 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.536 hERG inhibition (predictor II) Inhibitor 0.6318
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 166.7234865 predictedDarkChem Lite v0.1.0 [M-H]- 156.85863 predictedDeepCCS 1.0 (2019) [M+H]+ 167.4525865 predictedDarkChem Lite v0.1.0 [M+H]+ 159.21663 predictedDeepCCS 1.0 (2019) [M+Na]+ 167.2097865 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.30978 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Piao H, Nagai S, Tsurumaki T, Niki T, Higuchi H: Potentiation by neuropeptide Y of histamine H1 receptor-mediated contraction in rat blood vessels. Vascul Pharmacol. 2007 Apr;46(4):260-70. Epub 2006 Oct 27. [Article]
- Kesiova M, Alexandrova A, Yordanova N, Kirkova M, Todorov S: Effects of diphenhydramine and famotidine on lipid peroxidation and activities of antioxidant enzymes in different rat tissues. Pharmacol Rep. 2006 Mar-Apr;58(2):221-8. [Article]
- Hasala H, Moilanen E, Janka-Junttila M, Giembycz MA, Kankaanranta H: First-generation antihistamines diphenhydramine and chlorpheniramine reverse cytokine-afforded eosinophil survival by enhancing apoptosis. Allergy Asthma Proc. 2007 Jan-Feb;28(1):79-86. [Article]
- Wang Z, Woolverton WL: Self-administration of cocaine-antihistamine combinations: super-additive reinforcing effects. Eur J Pharmacol. 2007 Feb 28;557(2-3):159-60. Epub 2006 Dec 1. [Article]
- Ishikawa T, Takechi K, Rahman A, Ago J, Matsumoto N, Murakami A, Kamei C: Influences of histamine H1 receptor antagonists on maximal electroshock seizure in infant rats. Biol Pharm Bull. 2007 Mar;30(3):477-80. [Article]
- Havas TE, Cole P, Parker L, Oprysk D, Ayiomamitis A: The effects of combined H1 and H2 histamine antagonists on alterations in nasal airflow resistance induced by topical histamine provocation. J Allergy Clin Immunol. 1986 Nov;78(5 Pt 1):856-60. [Article]
- Rubinstein R, Nissenkorn I, Cohen S: Acetylcholine mediation of the contractile response to histamine in human bladder detrusor muscle. Eur J Pharmacol. 1987 Oct 6;142(1):45-50. doi: 10.1016/0014-2999(87)90652-2. [Article]
- Casy AF, Drake AF, Ganellin CR, Mercer AD, Upton C: Stereochemical studies of chiral H-1 antagonists of histamine: the resolution, chiral analysis, and biological evaluation of four antipodal pairs. Chirality. 1992;4(6):356-66. doi: 10.1002/chir.530040606. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled acetylcholine receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- Liu H, Zheng Q, Farley JM: Antimuscarinic actions of antihistamines on the heart. J Biomed Sci. 2006 May;13(3):395-401. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [Article]
- Akutsu T, Kobayashi K, Sakurada K, Ikegaya H, Furihata T, Chiba K: Identification of human cytochrome p450 isozymes involved in diphenhydramine N-demethylation. Drug Metab Dispos. 2007 Jan;35(1):72-8. doi: 10.1124/dmd.106.012088. Epub 2006 Oct 4. [Article]
- Lessard E, Yessine MA, Hamelin BA, Gauvin C, Labbe L, O'Hara G, LeBlanc J, Turgeon J: Diphenhydramine alters the disposition of venlafaxine through inhibition of CYP2D6 activity in humans. J Clin Psychopharmacol. 2001 Apr;21(2):175-84. [Article]
- Flockhart Table of Drug Interactions [Link]
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- Molecular Weight
- 62751.08 Da
References
- Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54