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Imipramine

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Also known as AntideprinBerkomineCristaliaImipraminaMelipramineNSC-169866ORG-2463SermonilTrimipramine maleate impurityimipramine-SID11111330SID11111331SID26751600SID90341377SID104171178SID50100256SID50104254SID124880469SID144203725

Summary

Imipramine (CHEMBL11) is an approved small-molecule adrenergic uptake inhibitor (ATC N06AA02) targeting CHRM2, KCNJ6, and KCNJ5; indicated across 18 conditions including depressive disorder and gastroesophageal reflux disease.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N06AA02
  • Targets: 6 (CHRM2, KCNJ6, KCNJ5…)
  • Indications: 18 conditions
  • Clinical trials: 27
  • Chemistry: 280.4 Da · C19H24N2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL11
NameImipramine
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID3696
ChEBICHEBI:47499
ATCN06AA02
Molecular formulaC19H24N2
Molecular weight280.4
InChIKeyBCGWQEUPMDMJNV-UHFFFAOYSA-N

SMILES: CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31

IUPAC name: 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine

ChEBI definition: A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.

Pharmacological roles (ChEBI): adrenergic uptake inhibitor, EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, antidepressant.

Also known as: Antideprin, Berkomine, Cristalia, Imipramina, Imipramine, Melipramine, NSC-169866, ORG-2463, Sermonil, Trimipramine maleate impurity, imipramine-, imipramine

Parent form; salt/anhydrous children: CHEMBL1692, CHEMBL3989845

Patent coverage: 13,836 distinct patent families (48,893 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 48,575 (99%) of the total. 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
CHRM2M2 receptorAntagonist6.90%P08172
KCNJ6Kir3.2Antagonist4.30.1%P48051
KCNJ5Kir3.4Antagonist4.50%P48544
KCNH1Kv10.15.70.2%O95259
SLC6A2NETInhibition7.80.4%P23975
SLC6A4SERTInhibition7.690.7%P31645

Broader ChEMBL bioactivity targets: 73 (assay-derived). Sample: Microtubule-associated protein tau, Prelamin-A/C, Pleiotropic ABC efflux transporter of multiple drugs, Solute carrier family 22 member 2, Multidrug and toxin extrusion protein 1, Solute carrier family 22 member 2, Muscarinic acetylcholine receptor M4, 5-hydroxytryptamine receptor 2B, D(1B) dopamine receptor, Glutamate NMDA receptor.

Bioactivity

ChEMBL activities: 131 potent at pChembl ≥ 5 of 149 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
P3139010.22IC500.06nMCHEMBL_ACT_779382
SLC6A49.28Ki0.52nMCHEMBL_ACT_13341982
SLC6A49.11Ki0.77nMCHEMBL_ACT_6317052
SLC6A49.06IC500.88nMCHEMBL_ACT_16501777
SLC6A49.06IC500.88nMCHEMBL_ACT_16838471
SLC6A49Ki1nMCHEMBL_ACT_18188070
SLC6A48.96IC501.1nMCHEMBL_ACT_13342054
HTR3E8.96IC501.1nMCHEMBL_ACT_26333207
HTR3E8.96Ki1.1nMCHEMBL_ACT_26333262
P431408.77IC501.7nMCHEMBL_ACT_725564
SLC6A48.72Ki1.9nMCHEMBL_ACT_19226362
SLC6A48.7IC502nMCHEMBL_ACT_13336152
SLC6A48.7Ki2nMCHEMBL_ACT_16817151
SLC6A48.68Ki2.1nMCHEMBL_ACT_14738667
SLC6A48.68Ki2.1nMCHEMBL_ACT_15186971
SLC6A48.6Ki2.5nMCHEMBL_ACT_18891578
SLC6A48.59IC502.6nMCHEMBL_ACT_16579889
SLC6A48.49Ki3.2nMCHEMBL_ACT_2381341
SLC6A48.46IC503.5nMCHEMBL_ACT_13828631
SLC6A48.39IC504.1nMCHEMBL_ACT_19226363
SLC6A48.36IC504.4nMCHEMBL_ACT_1611139
Q608578.3Ki5nMCHEMBL_ACT_241155
SLC6A48.3Ki5nMCHEMBL_ACT_414938
SLC6A48.29IC505.1nMCHEMBL_ACT_16817103
SLC6A48.24Ki5.7nMCHEMBL_ACT_16579925
SLC6A48.17IC506.8nMCHEMBL_ACT_13469060
SLC6A48.16IC506.9nMCHEMBL_ACT_2381314
SLC6A48.14IC507.3nMCHEMBL_ACT_5165994
SLC6A48.12Ki7.57nMCHEMBL_ACT_2701463
SLC6A48.1IC508nMCHEMBL_ACT_2515842

Target pathways

Aggregated over 6 target gene(s): CHRM2, KCNJ6, KCNJ5, KCNH1, SLC6A2, SLC6A4.

Top Reactome pathways

34 total, by targets touching each:

PathwayTargetsGenes
Neuronal System4KCNH1, KCNJ5, KCNJ6, SLC6A4
Transmission across Chemical Synapses3KCNJ5, KCNJ6, SLC6A4
Potassium Channels3KCNH1, KCNJ5, KCNJ6
Neurotransmitter receptors and postsynaptic signal transmission2KCNJ5, KCNJ6
Activation of G protein gated Potassium channels2KCNJ5, KCNJ6
G protein gated Potassium channels2KCNJ5, KCNJ6
Inwardly rectifying K+ channels2KCNJ5, KCNJ6
SLC-mediated transport of neurotransmitters2SLC6A2, SLC6A4
GABA receptor activation2KCNJ5, KCNJ6
GABA B receptor activation2KCNJ5, KCNJ6
Activation of GABAB receptors2KCNJ5, KCNJ6
Inhibition of voltage gated Ca2+ channels via Gbeta/gamma subunits2KCNJ5, KCNJ6
Neurotransmitter clearance1SLC6A4
Voltage gated Potassium channels1KCNH1
Signal Transduction1CHRM2
Disease1SLC6A2
Membrane Trafficking1CHRM2
Signaling by GPCR1CHRM2
Class A/1 (Rhodopsin-like receptors)1CHRM2
Amine ligand-binding receptors1CHRM2
Serotonin clearance from the synaptic cleft1SLC6A4
Transport of small molecules1SLC6A2
GPCR downstream signalling1CHRM2
Muscarinic acetylcholine receptors1CHRM2
G alpha (i) signalling events1CHRM2
R-HSA-4253661SLC6A2
SLC-mediated transmembrane transport1SLC6A2
GPCR ligand binding1CHRM2
SLC transporter disorders1SLC6A2
Defective SLC6A2 causes orthostatic intolerance (OI)1SLC6A2

Dominant GO biological processes

GO termTargets
potassium ion transport3
monoatomic ion transport3
monoatomic ion transmembrane transport3
transmembrane transport3
chemical synaptic transmission2
regulation of monoatomic ion transmembrane transport2
potassium ion import across plasma membrane2
potassium ion transmembrane transport2
neurotransmitter transport2
amino acid transport2
response to xenobiotic stimulus2
obsolete monoamine transport2
sodium ion transmembrane transport2
neurotransmitter reuptake2
regulation of smooth muscle contraction1

Indications & clinical

Indications

18 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
gastroesophageal reflux disease3MONDO:0007186EFO:0003948
anxiety3MONDO:0011918EFO:0005230
dementia3MONDO:0001627HP:0000726
myocardial infarction3MONDO:0005068EFO:0000612
ventricular fibrillation3MONDO:0000190EFO:0004287
somatoform disorder2MONDO:0003117EFO:0009687
rosacea2MONDO:0006604EFO:1000760
dysthymic disorder1MONDO:0001442EFO:0008623
photosensitivity disease1MONDO:0006597HP:0000992
breast neoplasm0MONDO:0021100MONDO:0007254

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

Clinical trials

Total trials: 27.

Phase distribution

PhaseTrials
PHASE39
Not specified6
PHASE44
PHASE24
PHASE12
PHASE1/PHASE21
EARLY_PHASE11

Top trials by phase / activity

NCTPhaseStatusTitle
NCT00227955PHASE4COMPLETEDComparing Various Treatments for Achieving and Maintaining Remission of Depression
NCT00296777PHASE4COMPLETEDTreatment of Depression Following Multiple Brain Tests
NCT00404755PHASE4COMPLETEDDichotic Listening as a Predictor of Medication Response in Depression
NCT01047488PHASE4UNKNOWNImipramine and Pregabalin Combination in Painful Polyneuropathy
NCT00000464PHASE3COMPLETEDCardiac Arrest in Seattle: Conventional Versus Amiodarone Drug Evaluation (CASCADE)
NCT00000518PHASE3COMPLETEDElectrophysiologic Study Versus Electrocardiographic Monitoring (ESVEM)
NCT00005575PHASE3COMPLETEDTreatment of Non-Cardiac Chest Pain With Imipramine or Cognitive-Behavioral Therapy
NCT00164775PHASE3COMPLETEDThe Efficacy of Imipramine in Treatment of Refractory Functional Dyspepsia
NCT01179828PHASE3COMPLETEDLinking Altered Central Pain Processing and Genetic Polymorphism to Drug Efficacy in Chronic Low Back Pain (Predictio)
NCT01753128PHASE3COMPLETEDEfficacy of Imipramine for Treatment of Patients With Esophageal Hypersensitivity/ Functional Heartburn
NCT02374567PHASE3TERMINATEDPharmacovigilance in Gerontopsychiatric Patients
NCT04412876PHASE3WITHDRAWNComparisons of the Impact of Duloxetine Versus Imipramine on Therapeutic Efficacy, Psychological Distress, Sexual Function, Urethral and Bladder Wall Structure and Blood Flow in Women With Stress Urinary Incontinence: a Randomized Controlled Study
NCT05677295PHASE3UNKNOWNTherapeutic Efficacy in Women With Stress Urinary Incontinence
NCT06312813PHASE2RECRUITINGEvaluating Use of Topical Imipramine and Amitriptyline in Reducing Ultraviolet B Light-Induced Redness in Patients With Rosacea
NCT06778434PHASE2RECRUITINGThe Effect of Topical Imipramine on Photodynamic Therapy-Mediated Immunosuppression on Forearms or Face on US Veterans
NCT00000504PHASE2COMPLETEDCardiac Arrhythmia Pilot Study (CAPS)
NCT00296725PHASE1/PHASE2COMPLETEDDichotic Listening as a Predictor of Medication Response in Depression
NCT01518634PHASE2COMPLETEDImipramine Treatment for Patients With Multi-organ Bodily Distress Syndrome
NCT05688904PHASE1RECRUITINGThe Effect of Topical Imipramine on Pain and Effectiveness of Topical Photodynamic Therapy
NCT03102645PHASE1COMPLETEDDoes Single Dose Imipramine Affect the Opening Pressure of the Urethral and Anal Sphincter?
NCT03122444EARLY_PHASE1COMPLETEDImipramine on ER+ve and Triple Negative Breast Cancer
NCT06497647Not specifiedRECRUITINGNew Treatment for Nocturnal Enuresis in Children
NCT06778824Not specifiedRECRUITINGNeuroregulators for the Treatment of Diseases Associated With Esophageal-brain-gut Axis Communication Abnormalities.
NCT00004834Not specifiedCOMPLETEDRandomized Study of Cognitive-Behavioral Therapy vs Imipramine and Their Combination for Panic Disorder
NCT00206999Not specifiedCOMPLETEDThe Effect of Imipramine on Early Information Processing
NCT01028014Not specifiedCOMPLETEDMedication Effects on Periurethral Sensation,Urethral Sphincter Activity and Pressure Flow Parameters
NCT01896349Not specifiedUNKNOWNInterpersonal Psychotherapy for Treatment Resistant Depression

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (3) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

GuidelineSourceGene(s)DosingRecommendation
Annotation of DPWG Guideline for imipramine and CYP2C19DPWGCYP2C19yesyes
Annotation of DPWG Guideline for imipramine and CYP2D6DPWGCYP2D6yesyes
Annotation of CPIC Guideline for imipramine and CYP2C19, CYP2D6CPICCYP2C19;CYP2D6yesyes

PharmGKB also curates 4 clinical and 36 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

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.

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

MoleculeSourceStatusShared targets
HALOPERIDOLChEMBL + PubChemPhase 4 (approved)CHRM2, KCNH1, SLC6A2, SLC6A4
ACLIDINIUM BROMIDEChEMBL + PubChemPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
AFATINIBChEMBL + PubChemPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
AMITRIPTYLINEChEMBL + PubChemPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CHENODIOLChEMBL + PubChemPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
GENTIAN VIOLETChEMBL + PubChemPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
MefloquineChEMBL + PubChemPhase 4 (approved)KCNJ5, SLC6A2, SLC6A4
OLODATEROLChEMBL + PubChemPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
PIMAVANSERINChEMBL + PubChemPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
PropafenoneChEMBL + PubChemPhase 4 (approved)KCNJ5, SLC6A2, SLC6A4
TadalafilChEMBL + PubChemPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
UMECLIDINIUMChEMBL + PubChemPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
VorapaxarChEMBL + PubChemPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
AMBENONIUMChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
AMIODARONEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
AMOXAPINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
ARIPIPRAZOLEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
ASENAPINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
ASTEMIZOLEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
AZELASTINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
BAZEDOXIFENEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
BENZTROPINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
BENZYDAMINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
BOSUTINIBChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
BROMODIPHENHYDRAMINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
BROMPHENIRAMINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CARBINOXAMINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CHLORHEXIDINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CHLORPHENIRAMINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CHLORPROMAZINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CHLORPROTHIXENEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CINNARIZINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CITALOPRAMChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CLEMASTINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CLOMIPHENEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CLOMIPRAMINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CLOTRIMAZOLEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CLOZAPINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
COBIMETINIBChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CYCLOBENZAPRINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
CYPROHEPTADINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DEQUALINIUMChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DESIPRAMINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DESLORATADINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DESOGESTRELChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DEXBROMPHENIRAMINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DEXCHLORPHENIRAMINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DIBENZEPINChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DIPHENHYDRAMINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DOTHIEPINChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DOXAZOSINChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DOXEPINChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
DRONEDARONEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
EBASTINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
ECONAZOLEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
ETHOPROPAZINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
ETHYLESTRENOLChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
FLUOXETINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, SLC6A4
FLUPHENAZINEChEMBLPhase 4 (approved)CHRM2, SLC6A2, 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