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Identification
NameTranylcypromine
Accession NumberDB00752  (APRD00645)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
TranilciprominaSpanishINN
TransamineNot AvailableNot Available
TranylcyprominGermanINN
TranylcypromineFrenchINN
TranylcyprominumLatinINN
Salts
Name/CAS Structure Properties
Tranylcypromine Sulfate
Thumb Not applicable DBSALT000960
Brand names
NameCompany
JatrosomAristo Pharma
ParnateGlaxoSmithKline
Brand mixtures
Brand NameIngredients
Cuait-DTranylcypromine and Trifluoperazine
ParmodalinTranylcypromine and Trifluoperazine
CategoriesNot Available
CAS number155-09-9
WeightAverage: 133.1903
Monoisotopic: 133.089149357
Chemical FormulaC9H11N
InChI KeyInChIKey=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
IUPAC Name
(1R)-2-phenylcyclopropan-1-amine
SMILES
N[C@@H]1CC1C1=CC=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassNot Available
Direct parentBenzene and Substituted Derivatives
Alternative parentsPolyamines; Monoalkylamines
Substituentspolyamine; primary amine; primary aliphatic amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzene and substituted derivatives. These are aromatic compounds containing at least one benzene ring.
Pharmacology
IndicationFor the treatment of major depressive episode without melancholia.
PharmacodynamicsTranylcypromine 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 actionTranylcypromine 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.
AbsorptionInterindividual 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 bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half life1.5-3.2 hours in patients with normal renal and hepatic function
ClearanceNot Available
ToxicityIn 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9383
Caco-2 permeable + 0.7935
P-glycoprotein substrate Non-substrate 0.8349
P-glycoprotein inhibitor I Non-inhibitor 0.9566
P-glycoprotein inhibitor II Non-inhibitor 0.9899
Renal organic cation transporter Non-inhibitor 0.8659
CYP450 2C9 substrate Non-substrate 0.8439
CYP450 2D6 substrate Non-substrate 0.9115
CYP450 3A4 substrate Non-substrate 0.7604
CYP450 1A2 substrate Inhibitor 0.9106
CYP450 2C9 substrate Non-inhibitor 0.8659
CYP450 2D6 substrate Non-inhibitor 0.7879
CYP450 2C19 substrate Inhibitor 0.8748
CYP450 3A4 substrate Non-inhibitor 0.9372
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6942
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.6686
Biodegradation Ready biodegradable 0.5525
Rat acute toxicity 2.4266 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9807
hERG inhibition (predictor II) Non-inhibitor 0.9378
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Par pharmaceutical inc
Packagers
Dosage forms
FormRouteStrength
Tablet, film coatedOral10 mg
Prices
Unit descriptionCostUnit
Parnate 10 mg tablet1.64USDtablet
Tranylcypromine Sulfate 10 mg tablet1.3USDtablet
Tranylcypromine sulf 10 mg tablet1.25USDtablet
Parnate 10 mg Tablet0.41USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point79-80 °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 solubility1.49e+00 g/lALOGPS
logP1.5ALOGPS
logP1.34ChemAxon
logS-1.9ALOGPS
pKa (strongest basic)9.62ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area26.02ChemAxon
rotatable bond count1ChemAxon
refractivity41.7ChemAxon
polarizability15.33ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot 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
ResourceLink
KEGG CompoundC07155
PubChem Compound441233
PubChem Substance46505832
ChemSpider390008
Therapeutic Targets DatabaseDAP000081
PharmGKBPA451741
HET1LP
Drug Product Database1919598
RxListhttp://www.rxlist.com/cgi/generic2/tranylcypromine.htm
Drugs.comhttp://www.drugs.com/cdi/tranylcypromine.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/par1618.shtml
WikipediaTranylcypromine
ATC CodesN06AF04
AHFS Codes
  • 28:16.04.12
PDB Entries
FDA labelshow(152 KB)
MSDSshow(38.3 KB)
Interactions
Drug Interactions
Drug
AlfentanilPossible increased risk of serotonin syndrome.
AlmotriptanThe 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.
AmitriptylineIncreased 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.
AmoxapineIncreased 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.
ApraclonidineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha2-agonist, Apraclonidine. Concomitant therapy is contraindicated.
AtomoxetineThe MAO inhibitor, Tranylcypromine, may increase the central neurotoxic effects of the Atomoxetine. These agents should not be administered within 14 days of each other.
BenzphetamineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Benzphetamine. Concomitant therapy should be avoided.
BezafibrateMAO Inhibitors may enhance the adverse/toxic effect of Bezafibrate. Avoid concomitant use of bezafibrate with monoamine oxidase inhibitors (MAOIs) like tranylcypromine.
BrimonidineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha2-agonist, Brimonidine. Concomitant therapy is contraindicated.
BromocriptineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
BuprenorphineBuprenorphine 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.
BupropionThe MAO inhibitor, Tranylcypromine, may increase the central neurotoxic effects of the Bupropion. These agents should not be administered within 14 days of each other.
BuspironeBuspirone 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.
CabergolineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
CitalopramIncreased 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.
ClomipramineIncreased 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.
CyclobenzaprineIncreased risk of serotonin syndrome. Concomitant use should be avoided. These agents should not be administered within 14 days of each other.
DesipramineIncreased 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.
DesvenlafaxineIncreased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
DexfenfluraminePossible hypertensive crisis
DexmedetomidineTranylcypromine, a strong CYP2A6 inhibitor, may decrease the metabolism and clearance of Dexmedetomidine.
DextroamphetamineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Dextroamphetamine. Concomitant therapy should be avoided.
DextromethorphanIncreased risk of serotonin syndrome. Concomitant use should be avoided.
DextropropoxypheneIncreased risk of serotonin syndrome. Concomitant use should be avoided.
DiethylpropionPossible hypertensive crisis
DihydroergotamineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
DonepezilPossible antagonism of action
DoxepinIncreased 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.
DuloxetineIncreased 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.
EletriptanIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
EntacaponeAdditive inhibition of endogenous catecholamine metabolism may increase the therapeutic/adverse effects of both agents. Concomitant therapy should be avoided.
EphedrineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Ephedrine. Concomitant therapy should be avoided.
EpinephrineIncreased arterial pressure
Ergoloid mesylateIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
ErgonovineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
ErgotamineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
EscitalopramIncreased 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.
FenfluraminePossible hypertensive crisis
FenoterolIncreased arterial pressure
FentanylPossible increased risk of serotonin syndrome.
FluoxetineIncreased 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.
FluvoxamineIncreased 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.
FrovatriptanIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
FurazolidoneIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
GalantaminePossible antagonism of action
GuanethidineTranylcypromine may decrease the effect of guanethidine.
IfosfamideTranylcypromine, a strong CYP2A6 inhibitor, may decrease the metabolism and clearance of Ifosmadine.
ImipramineIncreased 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.
IsocarboxazidIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
L-DOPALevodopa may increase the adverse effects of Tranylcypromine. Risk of severe hypertension. Concomitant therapy should be avoided or monitored closely for adverse effects of Tranylcypromine.
LinezolidThe MAO inhibitor, Tranylcypromine, may increase the adverse effects of Linezolid. These agents should not be administered within 14 days of each other.
LisdexamfetamineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Lisdexamfetamine. Concomitant therapy should be avoided.
LithiumIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
MaprotilineMaprotiline may increase the adverse effects of the MAO inhibitor, Tranylcypromine. These agents should not be administered within 14 days of each other.
MazindolPossible hypertensive crisis
MephentermineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Mephentermine. Concomitant therapy should be avoided.
MethamphetamineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Methamphetamine. Concomitant therapy should be avoided.
MethotrimeprazinePossible severe adverse reaction with this combination
MethoxamineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Methoxamine. Concomitant therapy should be avoided.
MethyldopaThe MAO inhibitor, Tranylcypromine, may increase the adverse effects of Methyldopa. Concomitant therapy is contraindicated.
MethylergometrineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
MethylphenidateThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Methylphenidate. Concomitant therapy is contraindicated.
MidodrineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Midodrine. Concomitant therapy should be avoided.
MilnacipranIncreased 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.
MirtazapineThe MAO inhibitor, Tranylcypromine, may increase the central neurotoxic effects of the Mirtazapine. These agents should not be administered within 14 days of each other.
MoclobemideIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
NaratriptanIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
NefazodoneIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
NortriptylineIncreased 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.
OrciprenalineIncreased arterial pressure
OxymetazolineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Oxymetazoline. Concomitant therapy should be avoided.
ParoxetineIncreased 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.
PergolideIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
PethidineIncreased risk of serotonin syndrome. Concomitant use should be avoided.
PhendimetrazineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Phendimetrazine. Concomitant therapy should be avoided.
PhenelzineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
PhentermineThe MAO inhibitor, tranylcypromine, may increase the vasopressor effect of the amphetamine, phentermine. Concomitant therapy should be avoided.
PhenylephrineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Phenylephrine. Concomitant therapy should be avoided.
PhenylpropanolamineIncreased arterial pressure
PramlintideThe 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.
ProcarbazineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
PromethazineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
ProtriptylineIncreased 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.
PseudoephedrineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Pseudoephedrine. Concomitant therapy should be avoided.
RasagilineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
RemifentanilPossible increased risk of serotonin syndrome.
ReserpineAddition 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.
RizatriptanThe 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-AdenosylmethionineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
SelegilineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
SertralineIncreased 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.
SibutramineIncreased risk of serotonin syndrome. Avoid concomitant therapy.
St. John's WortIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
SufentanilPossible increased risk of serotonin syndrome.
SumatriptanThe 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.
TacrineThe 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.
TamoxifenThe CYP2D6 inhibitor, Tranylcypromine, may decrease the efficacy of Tamoxifen by reducing active metabolite production. Consider alternate therapy.
TamsulosinTranylcypromine, 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.
TerbutalineIncreased arterial pressure
TetrabenazineTetrabenazine may increase the adverse/toxic effects of Tranylcypromine. Concomitant therapy is contraindicated.
ThioridazineTranylcypromine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Thioridazine. Concomitant therapy is contraindicated.
TizanidineTranylcypromine may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
TolcaponeTolcapone 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.
TramadolTramadol 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.
TrazodoneIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
TrimethobenzamideTrimethobenzamide and Tranylcypromine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TrimipramineIncreased 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.
TriprolidineConcomitant 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.
TrospiumTrospium and Tranylcypromine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
VenlafaxineIncreased 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.
VilazodoneMAO Inhibitors may enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This may cause serotonin syndrome.
ZolmitriptanThe 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.

1. Amine oxidase [flavin-containing] A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] A P21397 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] B P27338 Details

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

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2A6 P11509 Details

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 January 06, 2014 09:20