Identification

Name
Tranylcypromine
Accession Number
DB00752  (APRD00645)
Type
Small Molecule
Groups
Approved, Investigational
Description

A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders (From AMA Drug Evaluations Annual, 1994, p311).

Tranylcypromine is a racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine with the chiral centers both located on the cylopropane ring. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).

Structure
Thumb
Synonyms
  • (±)-trans-2-phenylcyclopropylamine
  • (1R*,2S*)-2-phenylcyclopropan-1-amine
  • DL-tranylcypromine
  • Racemic Tranylcypromine
  • Tranilcipromina
  • trans-2-phenylcyclopropylamine
  • trans-DL-2-Phenylcyclopropylamine
  • Transamine
  • Tranylcypromin
  • Tranylcypromine
  • Tranylcyprominum
External IDs
SKF 385 / SKF Trans-385
Product Ingredients
IngredientUNIICASInChI Key
Tranylcypromine sulfate7ZAT6ES87013492-01-8BKPRVQDIOGQWTG-KAVFMPKWSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ParnateTablet, film coated10 mg/1OralGlaxosmithkline Inc1989-06-232014-04-01Us0007 447120180907 15195 cu3siv
ParnateTablet10 mgOralGlaxosmithkline Inc1992-12-31Not applicableCanada
ParnateTablet, film coated10 mg/1OralGlaxosmithkline Inc2013-01-14Not applicableUs
ParnateTablet, film coated10 mg/1OralConcordia Pharmaceuticals Inc.2013-01-14Not applicableUs
ParnateTablet, film coated10 mg/1OralCovis Pharmaceuticals, Inc.2013-01-142017-09-30Us
ParnateTablet, film coated10 mg/1OralPhysicians Total Care, Inc.1994-08-152011-06-30Us
Tranylcypromine SulfateTablet10 mg/1OralRising Pharmaceuticals2012-01-09Not applicableUs
Tranylcypromine SulfateTablet10 mg/1OralRemedy Repack2014-04-012016-12-16Us64980 0183 01 nlmimage10 4b47a5dd
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Tranylcypromine SulfateTablet10 mg/1OralGolden State Medical Supply2013-10-18Not applicableUs
Tranylcypromine SulfateTablet, film coated10 mg/1OralActavis Pharma, Inc.2016-02-05Not applicableUs
Tranylcypromine SulfateTablet, film coated10 mg/1OralPar Pharmaceutical, Inc.2006-06-30Not applicableUs
International/Other Brands
Jatrosom (Aristo Pharma)
Categories
UNII
3E3V44J4Z9
CAS number
155-09-9
Weight
Average: 133.194
Monoisotopic: 133.089149358
Chemical Formula
C9H11N
InChI Key
AELCINSCMGFISI-UHFFFAOYSA-N
InChI
InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2
IUPAC Name
2-phenylcyclopropan-1-amine
SMILES
NC1CC1C1=CC=CC=C1

Pharmacology

Indication

For the treatment of major depressive episode without melancholia.

Associated Conditions
Pharmacodynamics

Tranylcypromine belongs to a class of antidepressants called monoamine oxidase inhibitors (MAOIs). Tranylcypromine is a non-hydrazine monoamine oxidase inhibitor with a rapid onset of activity. MAO is an enzyme that catalyzes the oxidative deamination of a number of amines, including serotonin, norepinephrine, epinephrine, and dopamine. Two isoforms of MAO, A and B, are found in the body. MAO-A is mainly found within cells located in the periphery and catalyzes the breakdown of serotonin, norepinephrine, epinephrine, dopamine and tyramine. MAO-B acts on phenylethylamine, norepinephrine, epinephrine, dopamine and tyramine, is localized extracellularly and is found predominantly in the brain. While the mechanism of MAOIs is still unclear, it is thought that they act by increasing free serotonin and norepinephrine concentrations and/or by altering the concentrations of other amines in the CNS. It has been postulated that depression is caused by low levels of serotonin and/or norepinephrine and that increasing serotonergic and norepinephrinergic neurotransmission results in relief of depressive symptoms. MAO A inhibition is thought to be more relevant to antidepressant activity than MAO B inhibition. Selective MAO B inhibitors, such as selegiline, have no antidepressant effects.

Mechanism of action

Tranylcypromine irreversibly and nonselectively inhibits monoamine oxidase (MAO). Within neurons, MAO appears to regulate the levels of monoamines released upon synaptic firing. Since depression is associated with low levels of monoamines, the inhibition of MAO serves to ease depressive symptoms, as this results in an increase in the concentrations of these amines within the CNS.

TargetActionsOrganism
AAmine oxidase [flavin-containing] A
inhibitor
Human
AAmine oxidase [flavin-containing] B
inhibitor
Human
Absorption

Interindividual variability in absorption. May be biphasic in some individuals. Peak plasma concentrations occur in one hour following oral administration with a secondary peak occurring within 2-3 hours. Biphasic absorption may represent different rates of absorption of the stereoisomers of the drug, though additional studies are required to confirm this.

Volume of distribution

1.1-5.7 L/kg

Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life

1.5-3.2 hours in patients with normal renal and hepatic function

Clearance
Not Available
Toxicity

In overdosage, some patients exhibit insomnia, restlessness and anxiety, progressing in severe cases to agitation, mental confusion and incoherence. Hypotension, dizziness, weakness and drowsiness may occur, progressing in severe cases to extreme dizziness and shock. A few patients have displayed hypertension with severe headache and other symptoms. Rare instances have been reported in which hypertension was accompanied by twitching or myoclonic fibrillation of skeletal muscles with hyperpyrexia, sometimes progressing to generalized rigidity and coma.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Tranylcypromine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Tranylcypromine is combined with (S)-Warfarin.
2,4-thiazolidinedioneTranylcypromine may increase the hypoglycemic activities of 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineTranylcypromine may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineTranylcypromine may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineTranylcypromine may increase the hypertensive activities of 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Tranylcypromine.
3,5-DinitrocatecholThe risk or severity of adverse effects can be increased when 3,5-Dinitrocatechol is combined with Tranylcypromine.
4-Bromo-2,5-dimethoxyamphetamineTranylcypromine may increase the hypertensive activities of 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Tranylcypromine.
Food Interactions
  • Avoid aged foods (chesse, red wine), pickled foods, cured foods (bacon/ham), chocolate, fava beans, beer, unless approved by your physician.
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (caffeine).
  • Avoid St. John's Wort.

References

General References
  1. Frieling H, Bleich S: Tranylcypromine: new perspectives on an "old" drug. Eur Arch Psychiatry Clin Neurosci. 2006 Aug;256(5):268-73. [PubMed:16927039]
  2. Nolen WA: [Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression]. Ned Tijdschr Geneeskd. 2003 Oct 4;147(40):1940-3. [PubMed:14574774]
External Links
KEGG Drug
D08625
KEGG Compound
C07155
PubChem Compound
5530
PubChem Substance
46505832
ChemSpider
5329
BindingDB
50113851
ChEBI
131512
ChEMBL
CHEMBL313833
Therapeutic Targets Database
DAP000081
PharmGKB
PA451741
HET
GJZ
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Tranylcypromine
ATC Codes
N06AF04 — Tranylcypromine
AHFS Codes
  • 28:16.04.12 — Monoamine Oxidase Inhibitors
FDA label
Download (152 KB)
MSDS
Download (38.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedNot AvailableTo Determine the Bioavailability of Tranylcypromine1
1RecruitingTreatmentAcute Myelogenous Leukaemia (AML) / Leukemias / Myelodysplastic Syndromes1
1, 2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
1, 2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML) / Myelodysplastic Syndrome1
3Not Yet RecruitingTreatmentIntracerebral Hemorrhage / Stroke Hemorrhagic1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3Unknown StatusTreatmentAcute Upper Gastrointestinal Hemorrhage1
4CompletedPreventionKnee Osteoarthritis (Knee OA)1
4CompletedTreatmentBipolar Disorder (BD)1
4CompletedTreatmentBipolar Disorder I or II1
4CompletedTreatmentDepression1
4CompletedTreatmentHaemorrhage1
4Not Yet RecruitingPreventionKnee Osteoarthritis (Knee OA)3
4RecruitingTreatmentHip Replacement, Total1
4TerminatedTreatmentMajor Depressive Disorder (MDD)2
Not AvailableCompletedTreatmentBipolar Disorder (BD)1
Not AvailableCompletedTreatmentBlood Loss / Congenital Heart Disease (CHD)1
Not AvailableUnknown StatusTreatmentTreatment Resistant Depression (TRD)1

Pharmacoeconomics

Manufacturers
  • Glaxosmithkline
  • Par pharmaceutical inc
Packagers
  • GlaxoSmithKline Inc.
  • Kaiser Foundation Hospital
  • Kali Laboratories Inc.
  • Par Pharmaceuticals
  • Physicians Total Care Inc.
Dosage forms
FormRouteStrength
TabletOral10 mg
Tablet, film coatedOral10 mg/1
TabletOral10 mg/1
Prices
Unit descriptionCostUnit
Parnate 10 mg tablet1.64USD tablet
Tranylcypromine Sulfate 10 mg tablet1.3USD tablet
Tranylcypromine sulf 10 mg tablet1.25USD tablet
Parnate 10 mg Tablet0.41USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)79-80 °C at 1.50E+00 mm HgNot Available
water solubility4.86E+004 mg/LNot Available
logP1.58HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.49 mg/mLALOGPS
logP1.5ALOGPS
logP1.34ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)9.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.7 m3·mol-1ChemAxon
Polarizability15.51 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9383
Caco-2 permeable+0.7935
P-glycoprotein substrateNon-substrate0.8349
P-glycoprotein inhibitor INon-inhibitor0.9566
P-glycoprotein inhibitor IINon-inhibitor0.9899
Renal organic cation transporterNon-inhibitor0.8659
CYP450 2C9 substrateNon-substrate0.8439
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateNon-substrate0.7604
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.8659
CYP450 2D6 inhibitorNon-inhibitor0.7879
CYP450 2C19 inhibitorInhibitor0.8748
CYP450 3A4 inhibitorNon-inhibitor0.9372
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6942
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6686
BiodegradationReady biodegradable0.5525
Rat acute toxicity2.4266 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9807
hERG inhibition (predictor II)Non-inhibitor0.9378
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Aralkylamines
Alternative Parents
Benzene and substituted derivatives / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Aralkylamine / Benzenoid / Monocyclic benzene moiety / Organopnictogen compound / Hydrocarbon derivative / Primary amine / Primary aliphatic amine / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Volz HP, Gleiter CH: Monoamine oxidase inhibitors. A perspective on their use in the elderly. Drugs Aging. 1998 Nov;13(5):341-55. [PubMed:9829163]
  3. Shioda K, Nisijima K, Yoshino T, Kato S: Mirtazapine abolishes hyperthermia in an animal model of serotonin syndrome. Neurosci Lett. 2010 Oct 4;482(3):216-9. doi: 10.1016/j.neulet.2010.07.039. Epub 2010 Jul 23. [PubMed:20655983]
  4. Gatch MB, Taylor CM, Flores E, Selvig M, Forster MJ: Effects of monoamine oxidase inhibitors on cocaine discrimination in rats. Behav Pharmacol. 2006 Mar;17(2):151-9. [PubMed:16495723]
  5. Lang W, Masucci JA, Caldwell GW, Hageman W, Hall J, Jones WJ, Rafferty BM: Liquid chromatographic and tandem mass spectrometric assay for evaluation of in vivo inhibition of rat brain monoamine oxidases (MAO) A and B following a single dose of MAO inhibitors: application of biomarkers in drug discovery. Anal Biochem. 2004 Oct 1;333(1):79-87. [PubMed:15351283]
  6. Shioda K, Nisijima K, Yoshino T, Kato S: Extracellular serotonin, dopamine and glutamate levels are elevated in the hypothalamus in a serotonin syndrome animal model induced by tranylcypromine and fluoxetine. Prog Neuropsychopharmacol Biol Psychiatry. 2004 Jul;28(4):633-40. [PubMed:15276688]
  7. Salsali M, Holt A, Baker GB: Inhibitory effects of the monoamine oxidase inhibitor tranylcypromine on the cytochrome P450 enzymes CYP2C19, CYP2C9, and CYP2D6. Cell Mol Neurobiol. 2004 Feb;24(1):63-76. [PubMed:15049511]
  8. Nolen WA: [Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression]. Ned Tijdschr Geneeskd. 2003 Oct 4;147(40):1940-3. [PubMed:14574774]
  9. Cohen C, Curet O, Perrault G, Sanger DJ: Reduction of oral ethanol self-administration in rats by monoamine oxidase inhibitors. Pharmacol Biochem Behav. 1999 Nov;64(3):535-9. [PubMed:10548268]
  10. Wiest SA, Steinberg MI: 3H[2-(2-benzofuranyl)-2-imidazoline] (BFI) binding in human platelets: modulation by tranylcypromine. Naunyn Schmiedebergs Arch Pharmacol. 1999 Aug;360(2):209-16. [PubMed:10494892]
  11. Loscher W, Lehmann H, Teschendorf HJ, Traut M, Gross G: Inhibition of monoamine oxidase type A, but not type B, is an effective means of inducing anticonvulsant activity in the kindling model of epilepsy. J Pharmacol Exp Ther. 1999 Mar;288(3):984-92. [PubMed:10027835]
  12. Todd KG, Baker GB: GABA-elevating effects of the antidepressant/antipanic drug phenelzine in brain: effects of pretreatment with tranylcypromine, (-)-deprenyl and clorgyline. J Affect Disord. 1995 Dec 13;35(3):125-9. [PubMed:8749840]
  13. Finberg JP, Youdim MB: Pharmacological properties of the anti-Parkinson drug rasagiline; modification of endogenous brain amines, reserpine reversal, serotonergic and dopaminergic behaviours. Neuropharmacology. 2002 Dec;43(7):1110-8. [PubMed:12504917]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Volz HP, Gleiter CH: Monoamine oxidase inhibitors. A perspective on their use in the elderly. Drugs Aging. 1998 Nov;13(5):341-55. [PubMed:9829163]
  3. Shioda K, Nisijima K, Yoshino T, Kato S: Mirtazapine abolishes hyperthermia in an animal model of serotonin syndrome. Neurosci Lett. 2010 Oct 4;482(3):216-9. doi: 10.1016/j.neulet.2010.07.039. Epub 2010 Jul 23. [PubMed:20655983]
  4. Gatch MB, Taylor CM, Flores E, Selvig M, Forster MJ: Effects of monoamine oxidase inhibitors on cocaine discrimination in rats. Behav Pharmacol. 2006 Mar;17(2):151-9. [PubMed:16495723]
  5. Lang W, Masucci JA, Caldwell GW, Hageman W, Hall J, Jones WJ, Rafferty BM: Liquid chromatographic and tandem mass spectrometric assay for evaluation of in vivo inhibition of rat brain monoamine oxidases (MAO) A and B following a single dose of MAO inhibitors: application of biomarkers in drug discovery. Anal Biochem. 2004 Oct 1;333(1):79-87. [PubMed:15351283]
  6. Shioda K, Nisijima K, Yoshino T, Kato S: Extracellular serotonin, dopamine and glutamate levels are elevated in the hypothalamus in a serotonin syndrome animal model induced by tranylcypromine and fluoxetine. Prog Neuropsychopharmacol Biol Psychiatry. 2004 Jul;28(4):633-40. [PubMed:15276688]
  7. Salsali M, Holt A, Baker GB: Inhibitory effects of the monoamine oxidase inhibitor tranylcypromine on the cytochrome P450 enzymes CYP2C19, CYP2C9, and CYP2D6. Cell Mol Neurobiol. 2004 Feb;24(1):63-76. [PubMed:15049511]
  8. Nolen WA: [Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression]. Ned Tijdschr Geneeskd. 2003 Oct 4;147(40):1940-3. [PubMed:14574774]
  9. Cohen C, Curet O, Perrault G, Sanger DJ: Reduction of oral ethanol self-administration in rats by monoamine oxidase inhibitors. Pharmacol Biochem Behav. 1999 Nov;64(3):535-9. [PubMed:10548268]
  10. Wiest SA, Steinberg MI: 3H[2-(2-benzofuranyl)-2-imidazoline] (BFI) binding in human platelets: modulation by tranylcypromine. Naunyn Schmiedebergs Arch Pharmacol. 1999 Aug;360(2):209-16. [PubMed:10494892]
  11. Loscher W, Lehmann H, Teschendorf HJ, Traut M, Gross G: Inhibition of monoamine oxidase type A, but not type B, is an effective means of inducing anticonvulsant activity in the kindling model of epilepsy. J Pharmacol Exp Ther. 1999 Mar;288(3):984-92. [PubMed:10027835]
  12. Todd KG, Baker GB: GABA-elevating effects of the antidepressant/antipanic drug phenelzine in brain: effects of pretreatment with tranylcypromine, (-)-deprenyl and clorgyline. J Affect Disord. 1995 Dec 13;35(3):125-9. [PubMed:8749840]
  13. Finberg JP, Youdim MB: Pharmacological properties of the anti-Parkinson drug rasagiline; modification of endogenous brain amines, reserpine reversal, serotonergic and dopaminergic behaviours. Neuropharmacology. 2002 Dec;43(7):1110-8. [PubMed:12504917]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-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 performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Taavitsainen P, Juvonen R, Pelkonen O: In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene. Drug Metab Dispos. 2001 Mar;29(3):217-22. [PubMed:11181487]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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
  1. Salsali M, Holt A, Baker GB: Inhibitory effects of the monoamine oxidase inhibitor tranylcypromine on the cytochrome P450 enzymes CYP2C19, CYP2C9, and CYP2D6. Cell Mol Neurobiol. 2004 Feb;24(1):63-76. [PubMed:15049511]
  2. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data supporting this enzyme action are limited in the literature, and based on 1 in vitro study.
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
  1. Salsali M, Holt A, Baker GB: Inhibitory effects of the monoamine oxidase inhibitor tranylcypromine on the cytochrome P450 enzymes CYP2C19, CYP2C9, and CYP2D6. Cell Mol Neurobiol. 2004 Feb;24(1):63-76. [PubMed:15049511]
Details
4. Cytochrome P450 2C19
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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
  1. Stadel R, Yang J, Nalwalk JW, Phillips JG, Hough LB: High-affinity binding of [3H]cimetidine to a heme-containing protein in rat brain. Drug Metab Dispos. 2008 Mar;36(3):614-21. Epub 2007 Dec 19. [PubMed:18094038]
  2. Salsali M, Holt A, Baker GB: Inhibitory effects of the monoamine oxidase inhibitor tranylcypromine on the cytochrome P450 enzymes CYP2C19, CYP2C9, and CYP2D6. Cell Mol Neurobiol. 2004 Feb;24(1):63-76. [PubMed:15049511]
  3. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data supported only by in vitro studies.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Taavitsainen P, Juvonen R, Pelkonen O: In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene. Drug Metab Dispos. 2001 Mar;29(3):217-22. [PubMed:11181487]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on November 20, 2018 13:19