imipramine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
substances of the imipramine group 1427 50-49-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • imipramine
  • prazepine
  • melipramine
  • imipramine hydrochloride
  • imipramine pamoate
  • imipramine HCl
The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.
  • Molecular weight: 280.42
  • Formula: C19H24N2
  • CLOGP: 5.04
  • LIPINSKI: 1
  • HAC: 2
  • HDO: 0
  • TPSA: 6.48
  • ALOGS: -3.63
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.10 g O
0.10 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 5.09 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 42 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 12 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 13 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.08 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 16 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 16, 1959 FDA

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
Completed suicide 229.79 39.56 60 363 20974 2336688
Toxicity to various agents 159.92 39.56 50 373 32704 2324958
Cardio-respiratory arrest 88.85 39.56 24 399 9122 2348540
Overdose 82.46 39.56 27 396 19880 2337782
Drug hypersensitivity 69.91 39.56 30 393 46613 2311049
Hallucination, auditory 64.04 39.56 14 409 2178 2355484
Psychotic disorder 63.28 39.56 16 407 4663 2352999
Dyspnoea 57.77 39.56 31 392 78702 2278960
Electrocardiogram QT prolonged 55.15 39.56 16 407 7798 2349864
Paranoia 53.49 39.56 12 411 2095 2355567
Cardiac arrest 52.70 39.56 18 405 14912 2342750
Drug abuse 44.36 39.56 15 408 12011 2345651
Electrocardiogram QRS complex prolonged 43.32 39.56 9 414 1093 2356569
Hypotension 42.33 39.56 19 404 32417 2325245
Death 40.61 39.56 25 398 81443 2276219
Intentional product misuse 39.62 39.56 13 410 9476 2348186

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
Completed suicide 232.43 50.27 58 219 16254 1730250
Toxicity to various agents 217.39 50.27 62 215 29079 1717425
Neuroleptic malignant syndrome 79.22 50.27 18 259 3130 1743374
Serotonin syndrome 54.46 50.27 13 264 2775 1743729
Intentional overdose 54.35 50.27 16 261 7654 1738850
Overdose 53.32 50.27 19 258 16682 1729822

Pharmacologic Action:

SourceCodeDescription
ATC N06AA02 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Non-selective monoamine reuptake inhibitors
MeSH PA D018663 Adrenergic Agents
FDA EPC N0000175752 Tricyclic Antidepressant
MeSH PA D018759 Adrenergic Uptake Inhibitors
CHEBI has role CHEBI:35640 adrenergic uptake inhibitor
CHEBI has role CHEBI:35469 antidepressant
MeSH PA D000928 Antidepressive Agents
MeSH PA D000929 Antidepressive Agents, Tricyclic
MeSH PA D002491 Central Nervous System Agents
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D011619 Psychotropic Drugs

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Nocturnal enuresis indication 8009008
Depressive disorder indication 35489007
Neuralgia off-label use 16269008
Cataplexy off-label use 46263000
Anxiety off-label use 48694002
Narcolepsy off-label use 60380001 DOID:8986
Bulimia nervosa off-label use 78004001
Neuropathic pain off-label use 247398009
Panic disorder off-label use 371631005 DOID:594
Attention deficit hyperactivity disorder off-label use 406506008
Ocular hypertension contraindication 4210003 DOID:9282
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Bipolar disorder contraindication 13746004 DOID:3312
Electroconvulsive therapy contraindication 23835007
Alcohol intoxication contraindication 25702006
Hyperthyroidism contraindication 34486009 DOID:7998
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Paralytic ileus contraindication 55525008 DOID:8442
Schizophrenia contraindication 58214004 DOID:5419
Intestinal obstruction contraindication 81060008 DOID:8437
Epilepsy contraindication 84757009 DOID:1826
Kidney disease contraindication 90708001 DOID:557
Seizure disorder contraindication 128613002
Cerebrovascular accident contraindication 230690007
Mania contraindication 231494001
Hypomania contraindication 231496004
Disease of liver contraindication 235856003 DOID:409
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Syncope contraindication 271594007
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Surgical procedure contraindication 387713003
Angle-closure glaucoma contraindication 392291006 DOID:13550
Disorder of coronary artery contraindication 414024009
Myocardial infarction in recovery phase contraindication 418044006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.04 Basic
pKa2 5.01 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
Sodium-dependent serotonin transporter Transporter INHIBITOR Kd 8.85 WOMBAT-PK CHEMBL
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Kd 7.43 WOMBAT-PK CHEMBL
Potassium voltage-gated channel subfamily H member 1 Ion channel BLOCKER IC50 5.70 IUPHAR
Adenosine receptor A3 GPCR IC50 8.36 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.77 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.44 CHEMBL
Major prion protein Surface antigen EC50 5 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.28 WOMBAT-PK
Muscarinic acetylcholine receptor M5 GPCR Ki 7.08 WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR Ki 6.95 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 7.22 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 8.08 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 7.38 WOMBAT-PK
Histamine H1 receptor GPCR IC50 7.61 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 6.41 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR IC50 7.10 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR IC50 7.49 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 6.80 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 6.82 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.90 WOMBAT-PK
D(2) dopamine receptor GPCR Ki 6.17 WOMBAT-PK
Solute carrier family 22 member 2 Transporter IC50 5.22 WOMBAT-PK
Sodium-dependent dopamine transporter Transporter Ki 5.07 PDSP
5-hydroxytryptamine receptor 1A GPCR Ki 5.24 PDSP
Sodium-dependent serotonin transporter Transporter Ki 7.38 CHEMBL
Serotonin 2 (5-HT2) receptor GPCR Ki 7.64 CHEMBL
Dopamine receptor GPCR IC50 6.19 CHEMBL
Muscarinic acetylcholine receptor M5 GPCR IC50 6.52 CHEMBL
Sodium-dependent dopamine transporter Transporter Ki 7.38 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 8.77 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 6.59 CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 7.92 CHEMBL
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 4.66 CHEMBL
Transporter Transporter Ki 7.92 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 6.80 CHEMBL
Glutamate NMDA receptor Ion channel IC50 4.85 CHEMBL
Muscarinic acetylcholine receptor GPCR Ki 7.19 CHEMBL
Adrenergic receptor alpha-1 GPCR Ki 7.34 CHEMBL
D(2) dopamine receptor GPCR Ki 6.14 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 8.30 CHEMBL
Histamine H1 receptor GPCR IC50 10.22 CHEMBL
Serotonin (5-HT) receptor GPCR IC50 7.36 CHEMBL
G protein-activated inward rectifier potassium channel 2 Ion channel BLOCKER IC50 4.30 IUPHAR
G protein-activated inward rectifier potassium channel 4 Unclassified BLOCKER EC50 4.50 IUPHAR

External reference:

IDSource
D007099 MESH_DESCRIPTOR_UI
4019785 VUID
N0000147875 NUI
C0020934 UMLSCUI
D00815 KEGG_DRUG
72O4809PU1 UNII
1916 INN_ID
73-07-4 SECONDARY_CAS_RN
36113004 SNOMEDCT_US
5691 RXNORM
372718005 SNOMEDCT_US
d00259 MMSL
4019785 VANDF
001498 NDDF
CHEBI:47499 CHEBI
CHEMBL11 ChEMBL_ID
DB00458 DRUGBANK_ID
CHEMBL1692 ChEMBL_ID
3696 PUBCHEM_CID
CHEMBL2105257 ChEMBL_ID
CHEMBL3989845 ChEMBL_ID
357 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
TOFRANIL HUMAN PRESCRIPTION DRUG LABEL 1 0406-9920 TABLET, SUGAR COATED 10 mg ORAL ANDA 15 sections
TOFRANIL HUMAN PRESCRIPTION DRUG LABEL 1 0406-9921 TABLET, SUGAR COATED 25 mg ORAL ANDA 15 sections
TOFRANIL HUMAN PRESCRIPTION DRUG LABEL 1 0406-9922 TABLET, SUGAR COATED 50 mg ORAL ANDA 15 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1762 TABLET, FILM COATED 10 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1764 TABLET, FILM COATED 25 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1766 TABLET, FILM COATED 50 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-345 TABLET, FILM COATED 10 mg ORAL ANDA 15 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-346 TABLET, FILM COATED 25 mg ORAL ANDA 15 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-347 TABLET, FILM COATED 50 mg ORAL ANDA 15 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 49884-054 TABLET 10 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 49884-055 TABLET 25 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 49884-056 TABLET 50 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-0034 TABLET 25 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-0035 TABLET, FILM COATED 25 mg ORAL ANDA 15 sections
IMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51655-455 TABLET, FILM COATED 50 mg ORAL ANDA 12 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53489-330 TABLET, FILM COATED 10 mg ORAL ANDA 15 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53489-331 TABLET, FILM COATED 25 mg ORAL ANDA 15 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53489-332 TABLET, FILM COATED 50 mg ORAL ANDA 15 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54738-912 TABLET, FILM COATED 10 mg ORAL ANDA 15 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54738-913 TABLET, FILM COATED 25 mg ORAL ANDA 15 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54738-914 TABLET, FILM COATED 50 mg ORAL ANDA 15 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-2221 TABLET, FILM COATED 50 mg ORAL ANDA 13 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55289-144 TABLET, FILM COATED 25 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55700-709 TABLET, FILM COATED 10 mg ORAL ANDA 13 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55700-710 TABLET, FILM COATED 25 mg ORAL ANDA 13 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-095 TABLET 10 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-096 TABLET 25 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-097 TABLET 50 mg ORAL ANDA 14 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 63629-5028 TABLET, FILM COATED 25 mg ORAL ANDA 13 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 63629-8149 TABLET 10 mg ORAL ANDA 14 sections