tranylcypromine ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
2715 155-09-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tranylcypromine
  • (RS)-trans-2-Phenylcyclopropylamine
  • tranylcypromine sulfate
  • tranylcypromine hydrochloride
  • tranylcypromine HCl
  • parnate
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)
  • Molecular weight: 133.19
  • Formula: C9H11N
  • CLOGP: 1.48
  • LIPINSKI: 0
  • HAC: 1
  • HDO: 1
  • TPSA: 26.02
  • ALOGS: -1.95
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
10 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 48 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 6.44 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 1.326 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.253 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 23.335 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 9.795 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 34 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 51.500 % High 1
herg hERG pIC50 4.457 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 8.017 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 16.943 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 42.230 % High 1
kinase-safety-class ACVR2B,AKT2,AXL,BRAF,CAMK2B,CAMK2D,CDK5,EIF2AK3,ERBB2,GRK2,IRAK4,ITK,MAPK12,NTRK2,PDK2,PDK4,PRKDC,TEK,TGFBR1 19
kinase-selectivity-class AKT1,AKT2,AKT3,EIF2AK3,PDK4,PRKG1 6
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 4.325 High 1
mh-clint Mouse hepatocyte intrinsic clearance 54.702 High 1
mppb Mouse plasma protein binding (% unbound) 37.330 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.355 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 39.230 % High 1
rh-clint Rat hepatocyte intrinsic clearance 52.602 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 70.720 % High 1
rppb Rat plasma protein binding (% unbound) 34.570 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 887.156 uM High 1

Approvals:

DateAgencyCompanyOrphan
Feb. 21, 1961 FDA COVIS PHARMA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hypertensive crisis 210.16 48.73 50 1384 17734 90609279
Potentiating drug interaction 168.42 48.73 34 1400 5628 90621385
Labelled drug-food interaction medication error 115.16 48.73 16 1418 264 90626749
Drug interaction 81.90 48.73 52 1382 276401 90350612
Serotonin syndrome 76.65 48.73 27 1407 37860 90589153
Diet noncompliance 70.07 48.73 11 1423 429 90626584
Congenital central nervous system anomaly 62.00 48.73 10 1424 464 90626549
Food interaction 58.47 48.73 11 1423 1253 90625760
Atrioventricular septal defect 57.55 48.73 9 1425 342 90626671
Drug dose titration not performed 57.12 48.73 10 1424 762 90626251
Craniosynostosis 55.78 48.73 8 1426 167 90626846

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Jaw clicking 71.13 45.29 9 751 60 42620515
Conversion disorder 52.30 45.29 9 751 551 42620024
Yawning 49.30 45.29 9 751 773 42619802
Illusion 46.83 45.29 9 751 1020 42619555

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hypertensive crisis 189.45 43.54 47 1379 24325 110563548
Serotonin syndrome 107.85 43.54 37 1389 59116 110528757
Potentiating drug interaction 98.13 43.54 24 1402 11619 110576254
Drug interaction 72.36 43.54 56 1370 500127 110087746
Labelled drug-food interaction medication error 72.18 43.54 10 1416 200 110587673
Drug dose titration not performed 69.34 43.54 12 1414 1053 110586820
Food interaction 67.03 43.54 13 1413 2139 110585734
Contraindicated product administered 62.16 43.54 39 1387 248228 110339645
Neuroleptic malignant syndrome 56.95 43.54 20 1406 34039 110553834

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N06AF04 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Monoamine oxidase inhibitors, non-selective
FDA MoA N0000000184 Monoamine Oxidase Inhibitors
MeSH PA D000928 Antidepressive Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D008996 Monoamine Oxidase Inhibitors
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014151 Anti-Anxiety Agents
FDA EPC N0000175744 Monoamine Oxidase Inhibitor
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35474 anxiolytic drug
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:38623 EC 1.4.3.4 (monoamine oxidase) inhibitor
CHEBI has role CHEBI:50183 P450 inhibitor
CHEBI has role CHEBI:50514 vasoconstrictor agent
CHEBI has role CHEBI:131509 EC 1.14.99.66 (lysine-specific histone demethylase 1A) inhibitor

Related Drugs by ATC class:

N06AF Monoamine oxidase inhibitors, non-selective 5 drugs

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Major depressive disorder indication 370143000
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Bipolar disorder contraindication 13746004 DOID:3312
Feeling agitated contraindication 24199005
Orthostatic hypotension contraindication 28651003
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Anxiety contraindication 48694002
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Schizophrenia contraindication 58214004 DOID:5419
Cerebrovascular disease contraindication 62914000 DOID:6713
Diabetes mellitus contraindication 73211009 DOID:9351
Kidney disease contraindication 90708001 DOID:557
Seizure disorder contraindication 128613002
Liver function tests abnormal contraindication 166603001
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Hypoglycemic disorder contraindication 237630007
Syncope contraindication 271594007
Pheochromocytoma contraindication 302835009
Myelogram contraindication 367401004
Disorder of coronary artery contraindication 414024009
Severe Headache Disorder contraindication
Hypertensive Emergencies contraindication
Frequent Headache Disorder contraindication




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.31 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Amine oxidase [flavin-containing] B Enzyme INHIBITOR IC50 7.48 CHEMBL CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 5.23 PDSP
Sodium-dependent dopamine transporter Transporter Ki 5.29 PDSP
Cytochrome P450 2A6 Enzyme Ki 7.19 WOMBAT-PK
Amine oxidase [flavin-containing] A Enzyme IC50 6.62 CHEMBL
Cytochrome P450 2C19 Enzyme IC50 5.30 CHEMBL
Cytochrome P450 2B6 Enzyme IC50 5.16 CHEMBL
Lysine-specific histone demethylase 1A Enzyme Ki 4.60 CHEMBL
Lysine-specific histone demethylase 1B Enzyme IC50 4.46 CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 5.23 PDSP
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase Enzyme IC50 5.11 CHEMBL
Cationic trypsin Enzyme Ki 4.88 CHEMBL
D(2) dopamine receptor GPCR Ki 4.23 CHEMBL
Amine oxidase [flavin-containing] B Enzyme IC50 7.11 CHEMBL
Amine oxidase [flavin-containing] A Enzyme IC50 6.54 CHEMBL
D(3) dopamine receptor GPCR Ki 4.89 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane other Ki 5.75 CHEMBL
Sigma intracellular receptor 2 Membrane receptor Ki 5.21 CHEMBL

External reference:

IDSource
4019953 VUID
N0000148038 NUI
D00826 KEGG_DRUG
13492-01-8 SECONDARY_CAS_RN
4018013 VANDF
4019953 VANDF
C0040778 UMLSCUI
CHEBI:9652 CHEBI
1LP PDB_CHEM_ID
CHEMBL3989843 ChEMBL_ID
5530 PUBCHEM_CID
DB00752 DRUGBANK_ID
CHEMBL3989698 ChEMBL_ID
D014191 MESH_DESCRIPTOR_UI
986 INN_ID
5281 IUPHAR_LIGAND_ID
3E3V44J4Z9 UNII
10734 RXNORM
4529 MMSL
5608 MMSL
84239 MMSL
d00884 MMSL
001496 NDDF
004597 NDDF
372891006 SNOMEDCT_US
89092006 SNOMEDCT_US
89772006 SNOMEDCT_US
CHEMBL1255743 ChEMBL_ID
1986-47-6 SECONDARY_CAS_RN
3E3V44J4Z9 INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Tranylcypromine Sulfate Human Prescription Drug Label 1 0591-5590 TABLET, FILM COATED 10 mg ORAL NDA AUTHORIZED GENERIC 27 sections
Tranylcypromine HUMAN PRESCRIPTION DRUG LABEL 1 10135-739 TABLET 10 mg ORAL ANDA 28 sections
Tranylcypromine HUMAN PRESCRIPTION DRUG LABEL 1 43547-655 TABLET 10 mg ORAL ANDA 30 sections
PARNATE Human Prescription Drug Label 1 59212-447 TABLET, FILM COATED 10 mg ORAL NDA 27 sections
TRANYLCYPROMINE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 64380-176 TABLET, FILM COATED 10 mg ORAL ANDA 25 sections
Tranylcypromine HUMAN PRESCRIPTION DRUG LABEL 1 70518-4708 TABLET 10 mg ORAL ANDA 29 sections
Tranylcypromine Human Prescription Drug Label 1 70954-538 TABLET 10 mg ORAL ANDA 29 sections