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Phenelzine

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Also known as FenelzinaPhenethyl-hydrazineSID11111653SID11111654SID90341694SID50111200SID174006798PHENELZINE SULFATE

Summary

Phenelzine (CHEMBL1089) is an approved small molecule (ATC N06AF03) targeting CYP2C8, MAOA, and MAOB; indicated across 1 condition including depressive disorder.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N06AF03
  • Targets: 7 (CYP2C8, MAOA, MAOB…)
  • Indications: 1 condition
  • Clinical trials: 8
  • Chemistry: 136.19 Da · C8H12N2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1089
NamePhenelzine
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID3675
ATCN06AF03
Molecular formulaC8H12N2
Molecular weight136.19
InChIKeyRMUCZJUITONUFY-UHFFFAOYSA-N

SMILES: C1=CC=C(C=C1)CCNN

IUPAC name: 2-phenylethylhydrazine

Also known as: Fenelzina, Phenelzine, Phenethyl-hydrazine, phenelzine, SID11111653, SID11111654, SID90341694, SID50111200, PHENELZINE, SID174006798, PHENELZINE SULFATE

Parent form; salt/anhydrous children: CHEMBL1200895

Patent coverage: 5,097 distinct patent families (18,793 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
CYP2C8CYP2C8Inhibition5.140.2%P10632
MAOAMonoamine oxidase AIrreversible inhibition7.330.2%P21397
MAOBMonoamine oxidase BIrreversible inhibition7.820%P27338
AOC3amine oxidase copper containing 3Inhibition7.72.1%Q16853
SLC6A2NETInhibition50.4%P23975
SLC6A3DATInhibition5.080.2%Q01959
SLC6A4SERTInhibition50.7%P31645

Broader ChEMBL bioactivity targets: 25 (assay-derived). Sample: Survival motor neuron protein, Prelamin-A/C, NPC intracellular cholesterol transporter 1, Ras-related protein Rab-9A, Alpha-2A adrenergic receptor, Amine oxidase [flavin-containing] A, Thyrotropin receptor, Amine oxidase [flavin-containing] B, 5-hydroxytryptamine receptor 1A, Prostaglandin G/H synthase 1.

Bioactivity

ChEMBL activities: 47 potent at pChembl ≥ 5 of 60 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
NFKB18Potency10nMCHEMBL_ACT_3672617
NFKB18Potency10nMCHEMBL_ACT_4585353
AOC37.7IC5019.95nMCHEMBL_ACT_3432350
P213967.52IC5030nMCHEMBL_ACT_408027
P196437.12IC5076.3nMCHEMBL_ACT_408028
MAOB7.03Ki94nMCHEMBL_ACT_15163789
MAOB6.91Ki124nMCHEMBL_ACT_18195386
TSHR6.9Potency125.9nMCHEMBL_ACT_3915224
MAOB6.84IC50143nMCHEMBL_ACT_18195377
MAOA6.84IC50146nMCHEMBL_ACT_7715217
CYP2C96.8Potency158.5nMCHEMBL_ACT_5053540
CYP2C96.8AC50158.5nMCHEMBL_ACT_5996439
MAOA6.79Ki163nMCHEMBL_ACT_18195384
MAOA6.77AC50170nMCHEMBL_ACT_25159775
MAOA6.62IC50238nMCHEMBL_ACT_18195372
CYP2C196.5Potency316.2nMCHEMBL_ACT_4020137
CYP2C196.5AC50316.2nMCHEMBL_ACT_6017173
PTGS16.3AC50500.1nMCHEMBL_ACT_25206363
LMNA6.3Potency501.2nMCHEMBL_ACT_3631509
CYP2C196.1Potency794.3nMCHEMBL_ACT_4019505
CYP2C196.1AC50794.3nMCHEMBL_ACT_6060474
CYP2C196.1IC50800nMCHEMBL_ACT_7715147
PTGS16.05AC50890.5nMCHEMBL_ACT_25205432
CYP1A26AC501000nMCHEMBL_ACT_6016244
CYP2D66IC501000nMCHEMBL_ACT_7715151
HTR1A5.95AC501133nMCHEMBL_ACT_25165232
CYP2C85.92Ki1200nMCHEMBL_ACT_6075049
MAOA5.78AC501644nMCHEMBL_ACT_25160899
CYP3A45.7IC502000nMCHEMBL_ACT_7715155
CYP2D65.6Potency2512nMCHEMBL_ACT_4957653

Target pathways

Aggregated over 7 target gene(s): CYP2C8, MAOA, MAOB, AOC3, SLC6A2, SLC6A3, SLC6A4.

Top Reactome pathways

38 total, by targets touching each:

PathwayTargetsGenes
Neurotransmitter clearance3MAOA, SLC6A3, SLC6A4
Transmission across Chemical Synapses3MAOA, SLC6A3, SLC6A4
Neuronal System3MAOA, SLC6A3, SLC6A4
Metabolism3AOC3, MAOA, MAOB
Disease3MAOA, SLC6A2, SLC6A3
Biological oxidations3AOC3, MAOA, MAOB
Phase I - Functionalization of compounds3AOC3, MAOA, MAOB
SLC-mediated transport of neurotransmitters3SLC6A2, SLC6A3, SLC6A4
Amine Oxidase reactions2MAOA, MAOB
Biogenic amines are oxidatively deaminated to aldehydes by MAOA and MAOB2MAOA, MAOB
Dopamine clearance from the synaptic cleft2MAOA, SLC6A3
Serotonin clearance from the synaptic cleft2MAOA, SLC6A4
Transport of small molecules2SLC6A2, SLC6A3
R-HSA-4253662SLC6A2, SLC6A3
SLC-mediated transmembrane transport2SLC6A2, SLC6A3
SLC transporter disorders2SLC6A2, SLC6A3
Disorders of transmembrane transporters2SLC6A2, SLC6A3
Neurotransmitter release cycle1MAOA
Cytokine Signaling in Immune system1MAOA
Immune System1MAOA
Norepinephrine Neurotransmitter Release Cycle1MAOA
Xenobiotics1CYP2C8
CYP2E1 reactions1CYP2C8
Synthesis of epoxy (EET) and dihydroxyeicosatrienoic acids (DHET)1CYP2C8
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE)1CYP2C8
Enzymatic degradation of dopamine by COMT1MAOA
Enzymatic degradation of Dopamine by monoamine oxidase1MAOA
Metabolism of serotonin1MAOA
Signaling by Interleukins1MAOA
Defective MAOA causes BRUNS1MAOA

Dominant GO biological processes

GO termTargets
dopamine catabolic process3
neurotransmitter transport3
amino acid transport3
response to xenobiotic stimulus3
obsolete monoamine transport3
sodium ion transmembrane transport3
transmembrane transport3
dopamine uptake involved in synaptic transmission2
norepinephrine uptake2
neurotransmitter reuptake2
lipid hydroxylation1
obsolete organic acid metabolic process1
xenobiotic metabolic process1
steroid metabolic process1
estrogen metabolic process1

Indications & clinical

Indications

1 indication (1 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:0002009

Clinical trials

Total trials: 8.

Phase distribution

PhaseTrials
PHASE14
PHASE22
PHASE41
Not specified1

Top trials by phase / activity

NCTPhaseStatusTitle
NCT06580041PHASE4ENROLLING_BY_INVITATIONPrecision Care for Major Depressive Disorder
NCT01253642PHASE2TERMINATEDPhenelzine Sulfate and Docetaxel in Treating Patients With Prostate Cancer With Progressive Disease After First-Line Therapy With Docetaxel
NCT02217709PHASE2COMPLETEDPhenelzine Sulfate in Treating Patients With Non-metastatic Recurrent Prostate Cancer
NCT03505528PHASE1COMPLETEDAn Early Phase Study of Abraxane Combined With Phenelzine Sulfate in Patients With Metastatic or Advanced Breast Cancer
NCT03694119PHASE1COMPLETEDDrug-drug Interaction Study of Ozanimod With Tyramine to Evaluate the Effect on Pressor Response
NCT03979820PHASE1TERMINATEDA Study in Healthy People to Test How Combining BI 1467335 and Tyramine Affects Blood Pressure
NCT04978298PHASE1COMPLETEDStudy to Evaluate the Pressor Effect of Oral Tyramine During Ozanimod Treatment in Healthy Adult Participants
NCT02153281Not specifiedCOMPLETEDNeuroimaging MAO-B in Medication Free TR-MDD Using Novel Tracer

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

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.

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

MoleculeSourceStatusShared targets
CLOTRIMAZOLEChEMBLPhase 4 (approved)CYP2C8, MAOA, MAOB, SLC6A2, SLC6A3, SLC6A4
MICONAZOLEChEMBLPhase 4 (approved)MAOA, MAOB, SLC6A2, SLC6A3, SLC6A4
PRIMAQUINEChEMBLPhase 4 (approved)MAOA, MAOB, SLC6A2, SLC6A3, SLC6A4
saxagliptinPubChemApprovedCYP2C8, MAOA, SLC6A2, SLC6A3, SLC6A4
AfatinibChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
CRIZOTINIBChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
gentian violetChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
IdelalisibChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
OlodaterolChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
PimavanserinChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
REGORAFENIBChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
rifampinChEMBL + PubChemPhase 4 (approved)CYP2C8, SLC6A2, SLC6A3, SLC6A4
TadalafilChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
TAFAMIDISChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
TafenoquineChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
UmeclidiniumChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
VorapaxarChEMBL + PubChemPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
AMIODARONEChEMBLPhase 4 (approved)CYP2C8, SLC6A2, SLC6A3, SLC6A4
ARIPIPRAZOLEChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
COCAINEChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
DANAZOLChEMBLPhase 4 (approved)CYP2C8, SLC6A2, SLC6A3, SLC6A4
DEQUALINIUMChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
DEXTROAMPHETAMINEChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
GUANABENZChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
KETOCONAZOLEChEMBLPhase 4 (approved)CYP2C8, SLC6A2, SLC6A3, SLC6A4
NICARDIPINEChEMBLPhase 4 (approved)CYP2C8, SLC6A2, SLC6A3, SLC6A4
NITAZOXANIDEChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
NORTRIPTYLINEChEMBLPhase 4 (approved)CYP2C8, SLC6A2, SLC6A3, SLC6A4
PENTAMIDINEChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
PONATINIBChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
PYRVINIUMChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
SERTINDOLEChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
TAMOXIFENChEMBLPhase 4 (approved)CYP2C8, SLC6A2, SLC6A3, SLC6A4
TEGASERODChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
THIORIDAZINEChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
TRANYLCYPROMINEChEMBLPhase 4 (approved)MAOA, MAOB, SLC6A2, SLC6A3
TROGLITAZONEChEMBLPhase 4 (approved)MAOA, MAOB, SLC6A2, SLC6A3
XANOMELINEChEMBLPhase 4 (approved)MAOA, SLC6A2, SLC6A3, SLC6A4
AMEZINIUM METILSULFATEChEMBLPhase 2MAOA, SLC6A2, SLC6A3, SLC6A4
CIGLITAZONEChEMBLPhase 2MAOA, MAOB, SLC6A2, SLC6A4
DOMIPHENChEMBLPhase 2MAOA, SLC6A2, SLC6A3, SLC6A4
LUCANTHONEChEMBLPhase 2MAOA, SLC6A2, SLC6A3, SLC6A4
PIRLINDOLEChEMBLPhase 2MAOA, SLC6A2, SLC6A3, SLC6A4
PROFLAVINEChEMBLPhase 2MAOA, SLC6A2, SLC6A3, SLC6A4
ZOTEPINEChEMBLPhase 2MAOA, SLC6A2, SLC6A3, SLC6A4
Aclidinium BromidePubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
ApixabanPubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
ApremilastPubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
BinimetinibPubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
BosentanPubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
chenodiolPubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
DihydroergotaminePubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
EchothiophatePubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
FidaxomicinPubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
FulvestrantPubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
ImipenemPubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
LactulosePubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
Latanoprostene BunodPubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
levocarnitinePubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4
LinagliptinPubChemApprovedMAOA, SLC6A2, SLC6A3, SLC6A4

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