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Tranylcypromine

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Also known as NSC-80664Tranilciprominarel-Tranylcypromine(+/-)-TranylcypromineSID11111676tparac-TranylcyprominephenylcyclopropylamineTRANYLCYPROMINE SULFATETranylcypronrine(-)-Trans-PCPA

Summary

Tranylcypromine (CHEMBL3989843) is an approved small molecule (ATC N06AF04) targeting PTGIS, MAOA, and MAOB; indicated across 9 conditions including depressive disorder and anxiety.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N06AF04
  • Targets: 4 (PTGIS, MAOA, MAOB…)
  • Indications: 9 conditions
  • Clinical trials: 23
  • Chemistry: 266.4 Da · C18H22N2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL3989843
NameTranylcypromine
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID73417116
ATCN06AF04
Molecular formulaC18H22N2
Molecular weight266.4
InChIKeyIGLYMJRIWWIQQE-QUOODJBBSA-N

SMILES: C1[C@H]([C@@H]1N)C2=CC=CC=C2.C1[C@@H]([C@H]1N)C2=CC=CC=C2

IUPAC name: trans-(1S,2R)-2-phenylcyclopropan-1-amine;trans-(1R,2S)-2-phenylcyclopropan-1-amine

Also known as: NSC-80664, Tranilcipromina, Tranylcypromine, rel-Tranylcypromine, (+/-)-Tranylcypromine, tranylcypromine, SID11111676, (+/-)-tranylcypromine, tpa, rel-tranylcypromine, TRANYLCYPROMINE, rac-Tranylcypromine

Parent form; salt/anhydrous children: CHEMBL3989698

Patent coverage: 46 distinct patent families (70 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
PTGISCYP8A1Inhibition0.2%Q16647
MAOAMonoamine oxidase AInhibition4.70.2%P21397
MAOBMonoamine oxidase BInhibition4.720%P27338
KDM1Alysine demethylase 1AInhibition4.48.1%O60341

Broader ChEMBL bioactivity targets: 30 (assay-derived). Sample: Alpha-2A adrenergic receptor, Amine oxidase [flavin-containing] A, Amine oxidase [flavin-containing] B, 5-hydroxytryptamine receptor 1A, Sodium-dependent noradrenaline transporter, 5-hydroxytryptamine receptor 2C, Alpha-1A adrenergic receptor, D(3) dopamine receptor, Sodium-dependent dopamine transporter, Voltage-gated inwardly rectifying potassium channel KCNH2.

Bioactivity

ChEMBL activities: 85 potent at pChembl ≥ 5 of 140 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
KDM1A8.35IC504.5nMCHEMBL_ACT_25442533
MAOB8.03IC509.4nMCHEMBL_ACT_18957038
MAOB7.58Ki26nMCHEMBL_ACT_15163788
CYP2A67.1IC5080nMCHEMBL_ACT_19359917
MAOA7.07IC5085nMCHEMBL_ACT_18957036
CYP2A66.89Ki130nMCHEMBL_ACT_15468123
MAOA6.62IC50240nMCHEMBL_ACT_13920865
MAOB6.6IC50250nMCHEMBL_ACT_13920853
MAOB6.25IC50560nMCHEMBL_ACT_19111397
HTR1A6.25AC50567.2nMCHEMBL_ACT_25164773
MAOB6.22IC50600nMCHEMBL_ACT_16290311
MAOB6.22IC50600nMCHEMBL_ACT_26595359
MAOB6.1IC50800nMCHEMBL_ACT_18036653
ADRA2A6.08AC50827.5nMCHEMBL_ACT_25156178
MAOB6.05IC50890nMCHEMBL_ACT_15228717
CYP2A66.01IC50970nMCHEMBL_ACT_19359604
MAOA5.99IC501020nMCHEMBL_ACT_19111379
MAOB5.98IC501050nMCHEMBL_ACT_15137343
MAOA5.97IC501070nMCHEMBL_ACT_15228734
MAOA5.97IC501060nMCHEMBL_ACT_18036647
MAOA5.92IC501190nMCHEMBL_ACT_15137307
MAOA5.8AC501600nMCHEMBL_ACT_25159228
Q604925.75Ki1800nMCHEMBL_ACT_22430920
CYP2C195.72IC501900nMCHEMBL_ACT_15026116
CYP2A65.7Kd2000nMCHEMBL_ACT_15468146
MAOA5.7IC502000nMCHEMBL_ACT_16345495
MAOA5.7IC502000nMCHEMBL_ACT_26595185
MAOA5.68IC502100nMCHEMBL_ACT_13883991
CYP2C195.68IC502070nMCHEMBL_ACT_22971659
Q018275.66AC502200nMCHEMBL_ACT_25197338

Target pathways

Aggregated over 4 target gene(s): PTGIS, MAOA, MAOB, KDM1A.

Top Reactome pathways

51 total, by targets touching each:

PathwayTargetsGenes
Amine Oxidase reactions2MAOA, MAOB
Biogenic amines are oxidatively deaminated to aldehydes by MAOA and MAOB2MAOA, MAOB
Metabolism2MAOA, MAOB
Disease2KDM1A, MAOA
Biological oxidations2MAOA, MAOB
Phase I - Functionalization of compounds2MAOA, MAOB
Hemostasis1KDM1A
Neurotransmitter release cycle1MAOA
Neurotransmitter clearance1MAOA
Transmission across Chemical Synapses1MAOA
Neuronal System1MAOA
PIP3 activates AKT signaling1KDM1A
Cytokine Signaling in Immune system1MAOA
Signal Transduction1KDM1A
Immune System1MAOA
Norepinephrine Neurotransmitter Release Cycle1MAOA
Signaling by Rho GTPases1KDM1A
RHO GTPase Effectors1KDM1A
Eicosanoids1PTGIS
Synthesis of Prostaglandins (PG) and Thromboxanes (TX)1PTGIS
HDACs deacetylate histones1KDM1A
HDMs demethylate histones1KDM1A
Chromatin modifying enzymes1KDM1A
Enzymatic degradation of dopamine by COMT1MAOA
Enzymatic degradation of Dopamine by monoamine oxidase1MAOA
Dopamine clearance from the synaptic cleft1MAOA
Metabolism of serotonin1MAOA
Serotonin clearance from the synaptic cleft1MAOA
Signaling by Interleukins1MAOA
Chromatin organization1KDM1A

Dominant GO biological processes

GO termTargets
dopamine catabolic process2
prostaglandin biosynthetic process1
icosanoid metabolic process1
embryo implantation1
cyclooxygenase pathway1
positive regulation of peroxisome proliferator activated receptor signaling pathway1
negative regulation of nitric oxide biosynthetic process1
positive regulation of angiogenesis1
prostanoid biosynthetic process1
decidualization1
negative regulation of inflammatory response1
cellular response to interleukin-11
cellular response to interleukin-61
cellular response to hypoxia1
apoptotic signaling pathway1

Indications & clinical

Indications

9 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
depressive disorder4MONDO:0002050MONDO:0002050
anxiety3MONDO:0011918EFO:0005230
dementia3MONDO:0001627HP:0000726
myelodysplastic syndrome1MONDO:0018881EFO:0000198
acute myeloid leukemia1MONDO:0018874EFO:0000222
orthostatic hypotension1MONDO:0005469EFO:0005252
leukemia1MONDO:0005059EFO:0000565

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 23.

Phase distribution

PhaseTrials
Not specified7
PHASE46
PHASE1/PHASE23
PHASE13
PHASE22
PHASE2/PHASE31
PHASE31

Top trials by phase / activity

NCTPhaseStatusTitle
NCT00021528PHASE4COMPLETEDSequenced Treatment Alternatives to Relieve Depression (STAR*D)
NCT00177567PHASE4COMPLETEDTreatment of Geriatric Bipolar Mood Disorders: A Pilot Study
NCT00296686PHASE4TERMINATEDSequential Tranylcypromine (TC), TC + Dextroamphetamine and TC + Triiodothyronine for Refractory Depression
NCT01031810PHASE4TERMINATEDPET Biomarkers in Treatment Resistant Depression
NCT01430455PHASE4COMPLETEDTranylcypromine Treatment of Bipolar Depression
NCT03213834PHASE4COMPLETEDFibrinolytic Therapy Versus Medical Thoracoscopy
NCT01835067PHASE2/PHASE3COMPLETEDIntravitreal tPA and C3F8 for the Treatment of Submacular Haemorrhage as a Complication of Neovascular AMD
NCT02374567PHASE3TERMINATEDPharmacovigilance in Gerontopsychiatric Patients
NCT00252239PHASE2TERMINATEDStudy of Tenecteplase (TNK) in Acute Ischemic Stroke (TNK-S2B)
NCT00612807PHASE1/PHASE2COMPLETEDTreatment of Mood and Marriage Study (TOMMS)
NCT01643902PHASE2COMPLETEDSafety of Intravenous Thrombolytics in Stroke on Awakening
NCT02261779PHASE1/PHASE2UNKNOWNPhase I/II Trial of ATRA and TCP in Patients With Relapsed or Refractory AML and no Intensive Treatment is Possible
NCT02717884PHASE1/PHASE2UNKNOWNStudy of Sensitization of Non-M3 AML Blasts to ATRA by Epigenetic Treatment With Tranylcypromine (TCP)
NCT00223691PHASE1COMPLETEDTreatment of Orthostatic Hypotension in Autonomic Failure
NCT00653393PHASE1COMPLETEDBioavailability Study of Tranylcypromine 10mg Tablets Under Fasting Conditions
NCT02273102PHASE1COMPLETEDStudy of TCP-ATRA for Adult Patients With AML and MDS
NCT05433051Not specifiedACTIVE_NOT_RECRUITINGA Comparison of Two Protocol for Maxillary Molar Intrusion Buccal Miniscrew and TPA Versus Vertical Holding Appliance
NCT00012558Not specifiedCOMPLETEDSystematic Treatment Enhancement Program for Bipolar Disorder (STEP-BD)
NCT01717417Not specifiedCOMPLETEDThree Dimensional Movement Analysis of Maxillary Impacted Canine: a Randomized Clincial Trial
NCT01896349Not specifiedUNKNOWNInterpersonal Psychotherapy for Treatment Resistant Depression
NCT02453373Not specifiedTERMINATEDHelping Stroke Patients With ThermoSuit Cooling
NCT04926428Not specifiedCOMPLETEDIn Situ Thrombolysis With tPA and Inflow Perfusion Analysis in Patient With Severe Covid-19 Infection
NCT05896618Not specifiedUNKNOWNEvaluation of Dental and Skeletal Effect of TPA and Nance as a Space Maintainers in Children: A Prospective Clinical Trial

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

200 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
PHENELZINEChEMBLPhase 4 (approved)KDM1A, MAOA, MAOB
CURCUMINChEMBLPhase 3KDM1A, MAOA, MAOB
QUERCETINChEMBLPhase 3KDM1A, MAOA, MAOB
RESVERATROLChEMBLPhase 3KDM1A, MAOA, MAOB
TEDIZOLIDChEMBL + PubChemPhase 4 (approved)MAOA, MAOB
CLOTRIMAZOLEChEMBLPhase 4 (approved)MAOA, MAOB
DANTHRONChEMBLPhase 4 (approved)MAOA, MAOB
FENTANYLChEMBLPhase 4 (approved)MAOA, MAOB
IPRONIAZIDChEMBLPhase 4 (approved)MAOA, MAOB
LINEZOLIDChEMBLPhase 4 (approved)MAOA, MAOB
MENADIONEChEMBLPhase 4 (approved)MAOA, MAOB
METHYLENE BLUE CATIONChEMBLPhase 4 (approved)MAOA, MAOB
MICONAZOLEChEMBLPhase 4 (approved)MAOA, MAOB
MOCLOBEMIDEChEMBLPhase 4 (approved)MAOA, MAOB
PARGYLINEChEMBLPhase 4 (approved)MAOA, MAOB
PIOGLITAZONEChEMBLPhase 4 (approved)MAOA, MAOB
PRIMAQUINEChEMBLPhase 4 (approved)MAOA, MAOB
RASAGILINEChEMBLPhase 4 (approved)MAOA, MAOB
ROSIGLITAZONEChEMBLPhase 4 (approved)MAOA, MAOB
SAFINAMIDEChEMBLPhase 4 (approved)MAOA, MAOB
SELEGILINEChEMBLPhase 4 (approved)MAOA, MAOB
TOLOXATONEChEMBLPhase 4 (approved)MAOA, MAOB
TROGLITAZONEChEMBLPhase 4 (approved)MAOA, MAOB
IDAZOXANChEMBLPhase 3MAOA, MAOB
RUTINChEMBLPhase 3KDM1A, MAOA
BROFAROMINEChEMBLPhase 2MAOA, MAOB
CIGLITAZONEChEMBLPhase 2MAOA, MAOB
CLORGILINEChEMBLPhase 2MAOA, MAOB
DAIDZEINChEMBLPhase 2MAOA, MAOB
FORMONONETINChEMBLPhase 2MAOA, MAOB
GENISTEINChEMBLPhase 2MAOA, MAOB
IADADEMSTATChEMBLPhase 2KDM1A, MAOA
ISOQUERCETINChEMBLPhase 2KDM1A, MAOA
LADOSTIGILChEMBLPhase 2MAOA, MAOB
LUTEOLINChEMBLPhase 2MAOA, MAOB
MOFEGILINEChEMBLPhase 2MAOA, MAOB
PHENAMAZOLINEChEMBLPhase 2MAOA, MAOB
PIPERINEChEMBLPhase 2MAOA, MAOB
SEMBRAGILINEChEMBLPhase 2MAOA, MAOB
SUTEZOLIDChEMBLPhase 2MAOA, MAOB
TIOXOLONEChEMBLPhase 2MAOA, MAOB
VAFIDEMSTATChEMBLPhase 2KDM1A, MAOB
CRIZOTINIBChEMBL + PubChemPhase 4 (approved)MAOA
REGORAFENIBChEMBL + PubChemPhase 4 (approved)MAOA
TAFAMIDISChEMBL + PubChemPhase 4 (approved)MAOA
ABROCITINIBChEMBLPhase 4 (approved)MAOA
AMILORIDEChEMBLPhase 4 (approved)MAOA
AMSACRINEChEMBLPhase 4 (approved)KDM1A
ANISINDIONEChEMBLPhase 4 (approved)MAOA
ARIPIPRAZOLEChEMBLPhase 4 (approved)MAOA
ATALURENChEMBLPhase 4 (approved)MAOA
BENOXAPROFENChEMBLPhase 4 (approved)MAOA
BERBERINEChEMBLPhase 4 (approved)KDM1A
BIFONAZOLEChEMBLPhase 4 (approved)MAOA
CABOZANTINIBChEMBLPhase 4 (approved)MAOA
CAPSAICINChEMBLPhase 4 (approved)KDM1A
CHLOROPROCAINEChEMBLPhase 4 (approved)MAOA
CHLORPROMAZINEChEMBLPhase 4 (approved)KDM1A
COCAINEChEMBLPhase 4 (approved)MAOA
COLISTINChEMBLPhase 4 (approved)KDM1A

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot