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Identification
Name Diphenhydramine
Accession Number DB01075 (APRD00587, DB06975)
Type small molecule
Groups approved
Description

A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
2-diphenylmethoxy-N,N-demthylethanamine
Diphenylhydramine
O-benzhydryldimethylaminoethanol
β-dimethylaminoethyl benzhydryl ether
Salts
  • Diphenhydramine Hcl
  • Diphenhydramine Salicylate
Brand names
Name Company
Aleryl
Alledryl
Allerdryl
Allergan B
Allergeval
Allergical
Allergin
Allergina
Allergival
Allermax Caplets
Ambodryl
Amidryl
Antomin
Automin
Bagodryl
Banophen
Baramine
Beldin
Belix
Ben-Allergin
Bena
Benachlor
Benadrin
Benadryl McNeil-PPC
Benapon
Benodin
Benodine
Benylan
Benylin
Betramin
Compoz
Dabylen
Debendrin
Dermistina
Dermodrin
Desentol
Diabenyl
Diabylen
Dibendrin
Dibenil
Dibondrin
Difedryl
Dihidral
Dimedrol
Dimedryl
Diphantine
Diphen
Diphen Cough
Diphenhist
Dormarex 2
Dryistan
Drylistan
Dylamon
Etanautine
Genahist
Histaxin
Hyadrine
Hydramine
Hyrexin
Ibiodral
Medidryl
Mephadryl
Nausen
Nervine Nighttime Sleep-Aid
Novamina
Nytol Quickcaps
Nytol Quickgels
Probedryl
Restamin
Rigidil
Siladryl
Silphen
Sleep-Eze D
Syntedril
Syntodril
Twilite Caplets
Unisom Sleepgels Maximum Strength
Vena
Vicks Formula 44
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Brand mixtures
Brand Name Ingredients
Ambenyl Cough Syrup Ammonium Chloride + Bromodiphenhydramine Hydrochloride + Codeine Phosphate + Diphenhydramine Hydrochloride + Potassium Guaiacol Sulphonate
Benadryl Decongestant Tablets Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Bye Bye Bite Lot Benzocaine + Diphenhydramine Hydrochloride + Menthol
Caladryl Cream Calamine + Diphenhydramine Hydrochloride
Caladryl Lotion Calamine + Diphenhydramine Hydrochloride
Calamine Lotion W Antihistamine Calamine + Diphenhydramine Hydrochloride
Calamine Lotion with Antih Lot Calamine + Diphenhydramine Hydrochloride + Zinc Oxide
Calamine W Antihistamine Lotion Calamine + Diphenhydramine Hydrochloride
Calmylin #4 Syr Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride
Children's Tylenol Allergy - D Chewable Tablets Acetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Children's Tylenol Allergy-D Suspension Acetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Contac Day & Night Sinus/Allergy Caplet Acetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Contac-C Ext.Stren.Night Time Cough,Cold&Flu Acetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Cough Syr W Codeine Diphenhyd Hcl & Ammon Cl Ammonium Chloride + Codeine Phosphate + Diphenhydramine Hydrochloride
Dm Cough Syr Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride
Dm Plus Cough Syrup Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride
Dm Syrup Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride
Pulmorex Expectorant Liq Ammonium Chloride + Diphenhydramine Hydrochloride + Guaifenesin
Salonpas Medicated Plaster Borneol + Camphor + Diphenhydramine + Menthol + Methyl Salicylate + Olive Oil + Rosin + Thymol + Zinc Oxide
Sinutab N.T. Regular Strength Caplets Acetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Sting Kure - Liq Benzocaine + Camphor + Diphenhydramine Hydrochloride + Phenol
Sting-Eze-Liq Benzocaine + Camphor + Diphenhydramine Hydrochloride + Phenol
Suppress Cough Syr W.Cod.Diphen.Hcl Amm.Chl. Ammonium Chloride + Codeine Phosphate + Diphenhydramine Hydrochloride
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Categories
  • Hypnotics and Sedatives
  • Antiemetics
  • Antiparkinson Agents
  • Antidyskinetics
  • Antipruritics
  • Anesthetics
  • Anti-Allergic Agents
  • Histamine H1 Antagonists
  • Anesthetics, Local
  • Antitussives
  • Ethanolamine Derivatives
CAS number 58-73-1
Weight Average: 255.3547
Monoisotopic: 255.162314299
Chemical Formula C17H21NO
InChI Key InChIKey=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
Plain Text
IUPAC Name
[2-(diphenylmethoxy)ethyl]dimethylamine
SMILES
CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Diphenhydramines
Substructures
  • Diphenhydramines
  • Benzyl Alcohols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Diphenylmethanes
  • Aromatic compounds
Pharmacology
Indication For the treatment of symptoms associated with Vertigo/Meniere's disease, nausea and vomiting, motion sickness and insect bite.
Pharmacodynamics Diphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, diphenhydramine competes with free histamine for binding at HA-receptor sites. Diphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of diphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
Mechanism of action Diphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.
Absorption Quickly absorbed with maximum activity occurring in approximately one hour.
Volume of distribution Not Available
Protein binding 98 to 99%
Metabolism Hepatic and renal
Route of elimination Little, if any, is excreted unchanged in the urine; most appears as the degradation products of metabolic transformation in the liver, which are almost completely excreted within 24 hours.
Half life 1-4 hours
Clearance Not Available
Toxicity LD50=500 mg/kg (orally in rats). Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular dysrhythmias, coma and death.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Mcneil consumer healthcare
  • Alra laboratories inc
  • Anabolic inc
  • Barr laboratories inc
  • Elkins sinn div ah robins co inc
  • Halsey drug co inc
  • Heather drug co inc
  • Impax laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lannett co inc
  • Lederle laboratories div american cyanamid co
  • Lnk international inc
  • Mk laboratories inc
  • Mutual pharmaceutical co inc
  • Newtron pharmaceuticals inc
  • Nexgen pharma inc
  • L perrigo co
  • Pioneer pharmaceuticals inc
  • Purepac pharmaceutical co
  • Private formulations inc
  • Roxane laboratories inc
  • Sandoz inc
  • Superpharm corp
  • Teva pharmaceuticals usa inc
  • Valeant pharmaceuticals international
  • Vangard laboratories inc div midway medical co
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Whiteworth towne paulsen inc
  • Hr cenci laboratories inc
  • Usl pharma inc
  • Cm bundy co
  • Kv pharmaceutical co
  • Naska pharmacal co inc div rugby darby group cosmetics
  • Pharmaceutical assoc inc div beach products
  • Alpharma us pharmaceuticals division
  • Abraxis pharmaceutical products
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia and critical care
  • Bel mar laboratories inc
  • Bioniche pharma usa llc
  • Hospira inc
  • Wyeth ayerst laboratories
  • International medication system
  • Parke davis div warner lambert co
  • Morton grove pharmaceuticals inc
  • Cumberland swan inc
  • Hi tech pharmacal co inc
  • Silarx pharmaceuticals inc
  • Warner chilcott co llc
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Cream Topical
Elixir Oral
Liquid Intramuscular
Liquid Intravenous
Liquid Oral
Lozenge Oral
Strip Oral
Syrup Oral
Tablet Oral
Tablet, chewable Oral
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Prices
Unit description Cost Unit
DiphenhydrAMINE HCl 100 50 mg capsule Bottle 13.99 USD bottle
Diphenhydramine 50 mg/ml 3.94 USD ml
Diphenhydramine 50 mg/ml vial 1.69 USD ml
DiphenhydrAMINE HCl 50 mg/ml vial 1.44 USD vial
Dytan 25 mg tablet chewable 1.37 USD tablet
Benadryl 50 mg/ml vial 1.36 USD ml
Diphenmax 25 mg tablet 1.24 USD tablet
Benadryl allergy 25 mg strips 0.45 USD strip
Unisom sleep aid tablet 0.34 USD tablet
Sleep-eze 3 tablet 0.29 USD tablet
Compoz 50 mg tablet 0.27 USD tablet
Sominex max str 50 mg caplet 0.27 USD caplet
Benadryl allergy fastmelt tablet 0.26 USD tablet
Unisom 25 mg sleeptabs 0.25 USD tablet
Unisom 50 mg sleepgels 0.25 USD each
Unisom sleepmelts 25 mg tablet 0.24 USD tablet
Nytol 25 mg tablet 0.23 USD tablet
Benadryl allergy-sinus caplet 0.22 USD caplet
Compoz 25 mg gelcap 0.2 USD capsule
Benadryl allergy 25 mg softgel 0.19 USD softgel capsule
Benadryl allergy 25 mg ultratab 0.19 USD tablet
Benadryl allergy-cold kapgels 0.19 USD each
Benadryl allergy-sinus kapgels 0.19 USD each
Benadryl-d allergy-sinus ultratab 0.19 USD tablet
Diphenhydramine hcl powder 0.17 USD g
Eql allergy 25 mg tablet 0.17 USD tablet
Nighttime sleep aid 25 mg cplt 0.17 USD caplet
Banophen anti-itch 2% cream 0.16 USD g
Benadryl itch relief stick 0.16 USD ml
Sominex 25 mg tablet 0.16 USD tablet
Benadryl allergy 25 mg kapgels 0.15 USD each
Allergy 25 mg tablet 0.14 USD tablet
Benadryl 25 mg kapseals 0.14 USD each
Benadryl itch stopping crm 0.14 USD g
DiphenhydrAMINE HCl 25 mg capsule 0.13 USD capsule
Diphenhist with zinc cream 0.12 USD g
Ra allergy 25 mg tablet 0.12 USD tablet
CVS Pharmacy allergy 25 mg tablet 0.11 USD tablet
Diphenhydramine 25 mg minitab 0.11 USD tablet
Simply sleep 25 mg caplet 0.11 USD caplet
Sleep ii tablet 0.11 USD tablet
Diphenhydramine 50 mg capsule 0.1 USD capsule
Benadryl 2% spray 0.09 USD ml
Diphenhist 50 mg tablet 0.09 USD tablet
Genahist 25 mg tablet 0.09 USD tablet
Ra sleep tablet 0.09 USD tablet
Banophen 25 mg tablet 0.08 USD tablet
Wal-dryl anti-itch spray 0.08 USD ml
CVS Pharmacy allergy 25 mg caplet 0.07 USD caplet
Nighttime sleep aid 25 mg caplet 0.07 USD caplet
CVS Pharmacy itch relief spray 0.06 USD ml
Diphen 25 mg capsule 0.06 USD capsule
Diphenhist 25 mg caplet 0.06 USD caplet
Benadryl anti-itch 0.45% gel 0.05 USD g
Diphenhydramine 50 mg caplet 0.05 USD caplet
Benadryl itch stopping gel 0.04 USD g
Child benadryl-d aller-sin liquid 0.04 USD ml
Diphenhydramine 25 mg capsule 0.04 USD capsule
Vicks 44d cough & head liquid 0.03 USD ml
Vicks 44e cough & chest liquid 0.03 USD ml
Banophen allergy liquid 0.02 USD ml
Diphenhydramine 25 mg tablet 0.02 USD tablet
Ra anti-tussive dm syrup 0.02 USD ml
Siladryl 12.5 mg/5 ml liquid 0.02 USD ml
Silphen cough syrup 0.02 USD ml
Silphen dm cough syrup 0.02 USD ml
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 168 °C PhysProp
boiling point 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 7.52e-02 g/l 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 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 79.93 ChemAxon
polarizability 29.86 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. 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. Pubmed
External Links
Resource Link
KEGG Drug D00300 Link_out
PubChem Compound 3100 Link_out
PubChem Substance 46505484 Link_out
ChemSpider 2989 Link_out
ChEBI 4636 Link_out
ChEMBL 4636 Link_out
Therapeutic Targets Database DAP000490 Link_out
PharmGKB PA449349 Link_out
IUPHAR 1224 Link_out
Guide to Pharmacology 1224 Link_out
HET 2PM Link_out
Drug Product Database 2244203 Link_out
RxList http://www.rxlist.com/cgi/generic/dihydram.htm Link_out
Drugs.com http://www.drugs.com/cdi/diphenhydramine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Diphenhydramine Link_out
ATC Codes
  • D04AA32
  • D04AA33
  • R06AA02
AHFS Codes
  • 04:04.04
PDB Entries Not Available
FDA label Not Available
MSDS show (73.5 KB)
Interactions
Drug Interactions
Drug Interaction
Atomoxetine Diphenhydramine, a moderate CYP2D6 inhibitor, may increase the therapeutic and adverse effects of atomoxetine by decreasing its metabolism.
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Mesoridazine Increased risk of cardiotoxicity and arrhythmias
Rivastigmine Possible antagonism of action
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Diphenhydramine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Tamoxifen Diphenhydramine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
Tamsulosin Diphenhydramine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Diphenhydramine is initiated, discontinued, or dose changed.
Thioridazine Increased risk of cardiotoxicity and arrhythmias
Tramadol Diphenhydramine may decrease the effect of Tramadol by decreasing active metabolite production.
Trimethobenzamide Trimethobenzamide and Diphenhydramine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Diphenhydramine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Trospium Trospium and Diphenhydramine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions
  • Avoid alcohol.
  • Take with food.
Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system

Organism class: human
UniProt ID: P35367 Link_out
Gene: HRH1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed
  6. 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. Pubmed
  7. 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. Pubmed
Enzymes

1. Cytochrome P450 2D6

Actions: substrate, inhibitor

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 antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
  2. 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. Pubmed
  3. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Actions: substrate

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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed

3. Cytochrome P450 2C9

Actions: substrate

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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan

UniProt ID: P11712 Link_out
Gene: CYP2C9
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed

4. Cytochrome P450 2C19

Actions: substrate

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 imipramine

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed

5. Cytochrome P450 2C18

Actions: substrate

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 unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P33260 Link_out
Gene: CYP2C18 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed

6. Cytochrome P450 2B6

Actions: substrate

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 unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P20813 Link_out
Gene: CYP2B6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed

7. Prostaglandin G/H synthase 1

Actions: substrate

May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

UniProt ID: P23219 Link_out
Gene: PTGS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
Transporters

1. Solute carrier family 22 member 2

Actions: inhibitor

Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity

UniProt ID: O15244 Link_out
Gene: SLC22A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed

2. Solute carrier family 22 member 1

Actions: inhibitor

Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase

UniProt ID: O15245 Link_out
Gene: SLC22A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed

3. Organic cation/carnitine transporter 2

Actions: inhibitor

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 cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

UniProt ID: O76082 Link_out
Gene: SLC22A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19