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Identification
Name Tranylcypromine
Accession Number DB00752 (APRD00645)
Type small molecule
Groups approved
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)
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Dl-Tranylcypromine
Parnate GlaxoSmithKline
Transamine
Brand mixtures Not Available
Categories
  • Antidepressants
  • Anti-anxiety Agents
  • Antidepressive Agents
  • Monoamine Oxidase Inhibitors
CAS number 155-09-9
Weight Average: 133.1903
Monoisotopic: 133.089149357
Chemical Formula C9H11N
InChI Key InChIKey=AELCINSCMGFISI-YGPZHTELSA-N
InChI
InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8?,9-/m1/s1
Plain Text
IUPAC Name
(1R)-2-phenylcyclopropan-1-amine
SMILES
N[C@@H]1CC1C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Phenylpropylamines
  • Amphetamines
Substructures
  • Aliphatic and Aryl Amines
  • Cyclopropane and Derivatives
  • Benzene and Derivatives
  • Phenethylamines
  • Aromatic compounds
  • Phenylpropylamines
  • Amphetamines
Pharmacology
Indication For the treatment of major depressive episode without melancholia.
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.
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
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Par pharmaceutical inc
Packagers
Dosage forms
Form Route Strength
Tablet, film coated Oral 10 mg
Prices
Unit description Cost Unit
Parnate 10 mg tablet 1.64 USD tablet
Tranylcypromine Sulfate 10 mg tablet 1.3 USD tablet
Tranylcypromine sulf 10 mg tablet 1.25 USD tablet
Parnate 10 mg Tablet 0.41 USD tablet
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 79-80 °C at 1.50E+00 mm Hg Not Available
water solubility 4.86E+004 mg/L Not Available
logP 1.58 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 1.49e+00 g/l ALOGPS
logP 1.5 ALOGPS
logP 1.34 ChemAxon
logS -1.9 ALOGPS
pKa (strongest basic) 9.62 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 26.02 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 41.7 ChemAxon
polarizability 15.33 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Frieling H, Bleich S: Tranylcypromine: new perspectives on an “old” drug. Eur Arch Psychiatry Clin Neurosci. 2006 Aug;256(5):268-73. Pubmed
  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
External Links
Resource Link
KEGG Compound C07155 Link_out
PubChem Compound 441233 Link_out
PubChem Substance 46505832 Link_out
ChemSpider 390008 Link_out
Therapeutic Targets Database DAP000081 Link_out
PharmGKB PA451741 Link_out
HET 1LP Link_out
Drug Product Database 1919598 Link_out
RxList http://www.rxlist.com/cgi/generic2/tranylcypromine.htm Link_out
Drugs.com http://www.drugs.com/cdi/tranylcypromine.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/par1618.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Tranylcypromine Link_out
ATC Codes
  • N06AF04
AHFS Codes
  • 28:16.04.12
PDB Entries
FDA label show (152 KB)
MSDS show (38.3 KB)
Interactions
Drug Interactions
Drug Interaction
Alfentanil Possible increased risk of serotonin syndrome.
Almotriptan The MAO inhibitor, Tranylcypromine, may reduce the metabolism and clearance of the serotonin 5-HT1D receptor agonist, Almotriptan. Risk of serotonin syndrome and Almotriptan toxicity. Concomitant therapy should be avoided.
Amitriptyline Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Amoxapine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Apraclonidine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha2-agonist, Apraclonidine. Concomitant therapy is contraindicated.
Atomoxetine The MAO inhibitor, Tranylcypromine, may increase the central neurotoxic effects of the Atomoxetine. These agents should not be administered within 14 days of each other.
Benzphetamine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Benzphetamine. Concomitant therapy should be avoided.
Bezafibrate MAO Inhibitors may enhance the adverse/toxic effect of Bezafibrate. Avoid concomitant use of bezafibrate with monoamine oxidase inhibitors (MAOIs) like tranylcypromine.
Brimonidine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha2-agonist, Brimonidine. Concomitant therapy is contraindicated.
Bromocriptine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Buprenorphine Buprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like tranylcypromine. When possible, avoid use of buprenorphine in patients who have used a monoamine oxidase inhibitor within the past 14 days due to possible severe adverse effects.
Bupropion The MAO inhibitor, Tranylcypromine, may increase the central neurotoxic effects of the Bupropion. These agents should not be administered within 14 days of each other.
Buspirone Buspirone may increase the adverse effects of Tranylcypromine. Elevation of blood pressure may occur. Concomitant therapy also may increase the risk of serotonin syndrome. Concomitant therapy should be avoided.
Cabergoline Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Citalopram Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Clomipramine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Cyclobenzaprine Increased risk of serotonin syndrome. Concomitant use should be avoided. These agents should not be administered within 14 days of each other.
Desipramine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Desvenlafaxine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Dexfenfluramine Possible hypertensive crisis
Dexmedetomidine Tranylcypromine, a strong CYP2A6 inhibitor, may decrease the metabolism and clearance of Dexmedetomidine.
Dextroamphetamine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Dextroamphetamine. Concomitant therapy should be avoided.
Dextromethorphan Increased risk of serotonin syndrome. Concomitant use should be avoided.
Diethylpropion Possible hypertensive crisis
Dihydroergotamine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Donepezil Possible antagonism of action
Doxepin Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Duloxetine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Eletriptan Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Entacapone Additive inhibition of endogenous catecholamine metabolism may increase the therapeutic/adverse effects of both agents. Concomitant therapy should be avoided.
Ephedrine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Ephedrine. Concomitant therapy should be avoided.
Epinephrine Increased arterial pressure
Ergoloid mesylate Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Ergonovine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Ergotamine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Escitalopram Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Fenfluramine Possible hypertensive crisis
Fenoterol Increased arterial pressure
Fentanyl Possible increased risk of serotonin syndrome.
Fluoxetine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Fluvoxamine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Frovatriptan Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Furazolidone Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Galantamine Possible antagonism of action
Guanethidine Tranylcypromine may decrease the effect of guanethidine.
Ifosfamide Tranylcypromine, a strong CYP2A6 inhibitor, may decrease the metabolism and clearance of Ifosmadine.
Imipramine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Isocarboxazid Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Levodopa Levodopa may increase the adverse effects of Tranylcypromine. Risk of severe hypertension. Concomitant therapy should be avoided or monitored closely for adverse effects of Tranylcypromine.
Linezolid The MAO inhibitor, Tranylcypromine, may increase the adverse effects of Linezolid. These agents should not be administered within 14 days of each other.
Lisdexamfetamine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Lisdexamfetamine. Concomitant therapy should be avoided.
Lithium Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Maprotiline Maprotiline may increase the adverse effects of the MAO inhibitor, Tranylcypromine. These agents should not be administered within 14 days of each other.
Mazindol Possible hypertensive crisis
Meperidine Increased risk of serotonin syndrome. Concomitant use should be avoided.
Mephentermine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Mephentermine. Concomitant therapy should be avoided.
Methamphetamine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Methamphetamine. Concomitant therapy should be avoided.
Methotrimeprazine Possible severe adverse reaction with this combination
Methoxamine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Methoxamine. Concomitant therapy should be avoided.
Methyldopa The MAO inhibitor, Tranylcypromine, may increase the adverse effects of Methyldopa. Concomitant therapy is contraindicated.
Methylergonovine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Methylphenidate The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Methylphenidate. Concomitant therapy is contraindicated.
Midodrine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Midodrine. Concomitant therapy should be avoided.
Milnacipran Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Mirtazapine The MAO inhibitor, Tranylcypromine, may increase the central neurotoxic effects of the Mirtazapine. These agents should not be administered within 14 days of each other.
Moclobemide Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Naratriptan Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Nefazodone Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Nortriptyline Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Orciprenaline Increased arterial pressure
Oxymetazoline The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Oxymetazoline. Concomitant therapy should be avoided.
Paroxetine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Pergolide Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Phendimetrazine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Phendimetrazine. Concomitant therapy should be avoided.
Phenelzine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Phentermine The MAO inhibitor, tranylcypromine, may increase the vasopressor effect of the amphetamine, phentermine. Concomitant therapy should be avoided.
Phenylephrine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Phenylephrine. Concomitant therapy should be avoided.
Phenylpropanolamine Increased arterial pressure
Pramlintide The anticholinergic effects of Tranylcypromine may be enhanced by Pramlintide. Additive effects of reduced GI motility may occur. Pramlintide slows gastic emptying and should not be used with drugs that alter GI motility (e.g. anticholinergics). Consider alternative treatments or use caution during concomitant therapy.
Procarbazine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Promethazine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Propoxyphene Increased risk of serotonin syndrome. Concomitant use should be avoided.
Protriptyline Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Pseudoephedrine The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Pseudoephedrine. Concomitant therapy should be avoided.
Rasagiline Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Remifentanil Possible increased risk of serotonin syndrome.
Reserpine Addition of Reserpine to Tranylcypromine therapy may induce paradoxical Reserpine effects, including peripheral hypertension and central exciation. Close monitoring for adverse effects is required. Addition of Tranylcypromine to Reserpine therapy may be less of a concern.
Rizatriptan The MAO inhibitor, Tranylcypromine, may reduce the metabolism and clearance of the serotonin 5-HT1D receptor agonist, Rizatriptan. Risk of serotonin syndrome and Rizatriptan toxicity. Concomitant therapy should be avoided.
S-Adenosylmethionine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Selegiline Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Sertraline Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Sibutramine Increased risk of serotonin syndrome. Avoid concomitant therapy.
St. John's Wort Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Sufentanil Possible increased risk of serotonin syndrome.
Sumatriptan The MAO inhibitor, Tranylcypromine, may reduce the metabolism and clearance of the serotonin 5-HT1D receptor agonist, Sumatriptan. Risk of serotonin syndrome and Sumatriptan toxicity. Concomitant therapy should be avoided.
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Tranylcypromine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. The metabolism of Tacrine, a CYP1A2 substrate, may be reduced by Tranylcypromine, a CYP1A2 inhibitor. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if doses are changed.
Tamoxifen The CYP2D6 inhibitor, Tranylcypromine, may decrease the efficacy of Tamoxifen by reducing active metabolite production. Consider alternate therapy.
Tamsulosin Tranylcypromine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Tranylcypromine is initiated, discontinued, or dose changed.
Terbutaline Increased arterial pressure
Tetrabenazine Tetrabenazine may increase the adverse/toxic effects of Tranylcypromine. Concomitant therapy is contraindicated.
Thioridazine Tranylcypromine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Thioridazine. Concomitant therapy is contraindicated.
Tizanidine Tranylcypromine may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
Tolcapone Tolcapone and Tranylcypromine decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
Tramadol Tramadol may increase the risk of serotonin syndrome and seizure induction by the MAO inhibitor, tranylcypromine. Tranylcypromine may decrease the effect of tramadol by decreasing active metabolite production.
Trazodone Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Trimethobenzamide Trimethobenzamide and Tranylcypromine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trimipramine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Avoid combination or monitor for symptoms of serotonin syndrome and/or hypertensive crisis.
Triprolidine Concomitant therapy with triprolidine and tranylcypromine, two anticholinergics and CNS depressants, may result in additive adverse/toxic effects. Monitor for enhanced anticholinergic and CNS depressant effects during concomitant therapy.
Trospium Trospium and Tranylcypromine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Venlafaxine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Vilazodone MAO Inhibitors may enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This may cause serotonin syndrome.
Zolmitriptan The MAO inhibitor, tranylcypromine, may increase the serum concentration of zolmitriptan by decreasing its metabolism. Concomitant therapy and use of zolmitriptan within two weeks of discontinuing tranylcypromine are contraindicated.
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.
Targets

1. Amine oxidase [flavin-containing] A

Pharmacological action: yes
Actions: inhibitor

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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine

Organism class: human
UniProt ID: P21397 Link_out
Gene: MAOA 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. Volz HP, Gleiter CH: Monoamine oxidase inhibitors. A perspective on their use in the elderly. Drugs Aging. 1998 Nov;13(5):341-55. Pubmed
  3. Shioda K, Nisijima K, Yoshino T, Kato S: Mirtazapine abolishes hyperthermia in an animal model of serotonin syndrome. Neurosci Lett. 2010 Jul 23. Pubmed
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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

2. Amine oxidase [flavin-containing] B

Pharmacological action: yes
Actions: inhibitor

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 tissues. MAOB preferentially degrades benzylamine and phenylethylamine

Organism class: human
UniProt ID: P27338 Link_out
Gene: MAOB 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. Volz HP, Gleiter CH: Monoamine oxidase inhibitors. A perspective on their use in the elderly. Drugs Aging. 1998 Nov;13(5):341-55. Pubmed
  3. Shioda K, Nisijima K, Yoshino T, Kato S: Mirtazapine abolishes hyperthermia in an animal model of serotonin syndrome. Neurosci Lett. 2010 Jul 23. Pubmed
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
Enzymes

1. Cytochrome P450 3A4

Actions: inhibitor

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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2D6

Actions: 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. 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
  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. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2C9

Actions: inhibitor

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. 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
  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. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2C19

Actions: inhibitor

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. 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
  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
  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. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 1A2

Actions: inhibitor

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. 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

6. Cytochrome P450 2E1

Actions: inhibitor

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 or carcinogenic forms

UniProt ID: P05181 Link_out
Gene: CYP2E1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 2A6

Actions: inhibitor

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. Constitutes the major nicotine C-oxidase

UniProt ID: P11509 Link_out
Gene: CYP2A6
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19