imipramine ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 ยตM/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
S (Water solubility) 50 mg/mL Bocci G, Oprea TI, Benet LZ

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AKT1,AKT2,AKT3,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,CHEK1,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,JAK3,MAP3K21,MAP3K7,MAPK10,MAPK12,MAPK7,MAPK9,MAPKAPK2,MET,MTOR,NTRK2,PAK4,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK 51
kinase-selectivity-class AXL,PDK4,SIK2,STK33,TTK 5
mdck-mdr1-bcrp-efflux MDCK-MDR1-BCRP efflux ratio 0.735 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pld-class Phospholipidosis risk class (1 = positive, 0 = negative) 1 High 1
rat-kpuu-brain Rat brain Kpuu 0.533 % High 1

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 124.59 18.44 77 3756 144981 90479633
Paranoia 71.23 18.44 25 3808 12883 90611731
Toxicity to various agents 70.42 18.44 73 3760 287773 90336841
Hallucination, auditory 66.03 18.44 25 3808 15950 90608664
Antidepressant drug level above therapeutic 58.05 18.44 11 3822 479 90624135
Psychotic disorder 52.88 18.44 26 3807 31204 90593410
Stress cardiomyopathy 34.78 18.44 15 3818 13340 90611274
Skin hyperpigmentation 32.99 18.44 12 3821 6839 90617775
Procedural hypotension 30.26 18.44 8 3825 1592 90623022
Sleep apnoea syndrome 27.53 18.44 17 3816 31730 90592884
Iris hyperpigmentation 26.61 18.44 4 3829 41 90624573
Cardio-respiratory arrest 25.02 18.44 21 3812 63119 90561495
Depressed level of consciousness 24.39 18.44 22 3811 72762 90551852
Respiratory arrest 24.31 18.44 16 3817 33295 90591319
Decreased activity 23.98 18.44 10 3823 8182 90616432
Urinary hesitation 22.56 18.44 7 3826 2456 90622158
Limb mass 20.09 18.44 7 3826 3521 90621093
Catatonia 19.80 18.44 8 3825 6048 90618566

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
Toxicity to various agents 56.73 24.09 62 1989 229074 42390210
Blepharospasm 55.82 24.09 13 2038 1355 42617929
Completed suicide 53.28 24.09 41 2010 96424 42522860
Long QT syndrome 44.99 24.09 13 2038 3154 42616130
Neuroleptic malignant syndrome 43.38 24.09 21 2030 21451 42597833
Pyelitis 40.80 24.09 7 2044 151 42619133
Muscle rigidity 37.71 24.09 16 2035 12043 42607241
Trismus 37.27 24.09 11 2040 2873 42616411
Dystonia 36.80 24.09 16 2035 12774 42606510
Delusion 25.56 24.09 13 2038 14721 42604563
Overdose 25.07 24.09 28 2023 105236 42514048
Cognitive disorder 24.41 24.09 17 2034 34155 42585129
Brain oedema 24.30 24.09 13 2038 16314 42602970

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
Completed suicide 153.86 18.28 111 5097 242270 110341821
Toxicity to various agents 93.77 18.28 114 5094 480441 110103650
Paranoia 64.96 18.28 28 5180 22346 110561745
Neuroleptic malignant syndrome 62.49 18.28 31 5177 34028 110550063
Hallucination, auditory 54.35 18.28 26 5182 26371 110557720
Antidepressant drug level above therapeutic 52.10 18.28 11 5197 746 110583345
Overdose 46.29 18.28 56 5152 233738 110350353
Psychotic disorder 40.82 18.28 27 5181 50910 110533181
Long QT syndrome 34.90 18.28 13 5195 7105 110576986
Pyelitis 33.98 18.28 7 5201 421 110583670
Stress cardiomyopathy 30.81 18.28 15 5193 15791 110568300
Procedural hypotension 30.14 18.28 9 5199 2496 110581595
Dystonia 29.09 18.28 17 5191 25788 110558303
Trismus 28.56 18.28 11 5197 6585 110577506
Electrocardiogram QT prolonged 26.41 18.28 29 5179 108931 110475160
Drug interaction 25.73 18.28 66 5142 500117 110083974
Respiratory depression 25.72 18.28 17 5191 31984 110552107
Skin hyperpigmentation 25.62 18.28 11 5197 8685 110575406
Cardio-respiratory arrest 24.96 18.28 29 5179 115807 110468284
Muscle rigidity 24.92 18.28 15 5193 24016 110560075
Electrocardiogram abnormal 22.89 18.28 13 5195 18696 110565395
Withdrawal syndrome 21.26 18.28 15 5193 31365 110552726
Parkinsonism 20.83 18.28 13 5195 22174 110561917
Decreased activity 20.15 18.28 10 5198 10964 110573127
Speech disorder 19.64 18.28 19 5189 61550 110522541
Iris hyperpigmentation 19.61 18.28 3 5205 31 110584060
Suicide attempt 19.19 18.28 24 5184 103370 110480721
Waxy flexibility 18.60 18.28 4 5204 296 110583795
Limb mass 18.55 18.28 7 5201 3962 110580129

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N06AA02 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Non-selective monoamine reuptake inhibitors
MeSH PA D000928 Antidepressive Agents
MeSH PA D000929 Antidepressive Agents, Tricyclic
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018663 Adrenergic Agents
MeSH PA D018759 Adrenergic Uptake Inhibitors
MeSH PA D049990 Membrane Transport Modulators
CHEBI has role CHEBI:35469 antidepressant
FDA EPC N0000175752 Tricyclic Antidepressant
CHEBI has role CHEBI:35474 anxiolytic drug
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35554 cardiovascular drug
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35640 adrenergic uptake inhibitor
CHEBI has role CHEBI:76779 EC 3.4.21.26 (prolyl oligopeptidase) inhibitor

Related Drugs by ATC class:

N06AA Non-selective monoamine reuptake inhibitors 20 drugs

Drug Use | Suggest Off label Use Form| |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




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 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 noradrenaline transporter Transporter INHIBITOR Kd 7.43 WOMBAT-PK CHEMBL
Sodium-dependent serotonin transporter Transporter INHIBITOR Kd 8.85 WOMBAT-PK CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.28 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 5.24 PDSP
5-hydroxytryptamine receptor 2A GPCR Ki 6.83 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 6.80 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR IC50 7.50 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR IC50 7.10 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 6.41 WOMBAT-PK
Histamine H1 receptor GPCR IC50 7.61 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 7.38 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 8.08 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 7.22 WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR Ki 6.95 WOMBAT-PK
Muscarinic acetylcholine receptor M5 GPCR Ki 7.08 WOMBAT-PK
Sodium-dependent dopamine transporter Transporter Ki 5.07 PDSP
Adenosine receptor A3 GPCR IC50 8.36 CHEMBL
Voltage-dependent N-type calcium channel subunit alpha-1B Ion channel IC50 4.66 CHEMBL
Major prion protein Surface antigen EC50 5 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.77 CHEMBL
Potassium voltage-gated channel subfamily H member 1 Ion channel BLOCKER IC50 5.70 IUPHAR
Solute carrier family 22 member 2 Transporter IC50 5.22 WOMBAT-PK
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.44 CHEMBL
Sphingomyelin phosphodiesterase Enzyme IC50 5.30 CHEMBL
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
Alpha-1A adrenergic receptor GPCR IC50 8.77 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 7.38 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.46 CHEMBL
Transporter Transporter Ki 7.92 CHEMBL
Sodium-dependent dopamine transporter Transporter Ki 7.38 CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 7.92 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 6.80 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
Muscarinic acetylcholine receptor M5 GPCR IC50 6.52 CHEMBL
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 4.66 CHEMBL
Glutamate NMDA receptor Ion channel IC50 4.85 CHEMBL
Muscarinic acetylcholine receptor GPCR Ki 7.19 CHEMBL
Serotonin (5-HT) receptor GPCR IC50 7.36 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 6.59 CHEMBL
Dopamine receptor GPCR IC50 6.19 CHEMBL
Adrenergic receptor alpha-1 GPCR Ki 7.34 CHEMBL
Serotonin 2 (5-HT2) receptor GPCR Ki 7.64 CHEMBL
G protein-activated inward rectifier potassium channel 4 Ion channel BLOCKER EC50 4.50 IUPHAR
G protein-activated inward rectifier potassium channel 2 Ion channel BLOCKER IC50 4.30 IUPHAR
Sigma intracellular receptor 2 Membrane receptor Ki 5.68 CHEMBL

External reference:

IDSource
4019785 VUID
N0000147875 NUI
D00815 KEGG_DRUG
73-07-4 SECONDARY_CAS_RN
113-52-0 SECONDARY_CAS_RN
10075-24-8 SECONDARY_CAS_RN
4017862 VANDF
4017863 VANDF
4019785 VANDF
C0020934 UMLSCUI
CHEBI:47499 CHEBI
IXX PDB_CHEM_ID
CHEMBL11 ChEMBL_ID
CHEMBL2105257 ChEMBL_ID
DB00458 DRUGBANK_ID
CHEMBL1692 ChEMBL_ID
CHEMBL3989845 ChEMBL_ID
D007099 MESH_DESCRIPTOR_UI
3696 PUBCHEM_CID
357 IUPHAR_LIGAND_ID
793 INN_ID
OGG85SX4E4 UNII
150816 RXNORM
2328 MMSL
4870 MMSL
4871 MMSL
81685 MMSL
d00259 MMSL
001498 NDDF
001499 NDDF
001500 NDDF
3378009 SNOMEDCT_US
36113004 SNOMEDCT_US
372718005 SNOMEDCT_US
4203009 SNOMEDCT_US
1916 INN_ID
OGG85SX4E4 INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 0054-0273 CAPSULE 75 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 0054-0274 CAPSULE 100 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 0054-0275 CAPSULE 125 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 0054-0276 CAPSULE 150 mg ORAL ANDA 20 sections
IMIPRAMINE PAMOATE HUMAN PRESCRIPTION DRUG LABEL 1 16590-963 CAPSULE 75 mg ORAL NDA 22 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-0035 TABLET, FILM COATED 25 mg ORAL ANDA 21 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-3148 TABLET, FILM COATED 25 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50436-2022 TABLET, FILM COATED 25 mg ORAL ANDA 21 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-1344 TABLET, FILM COATED 25 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-2221 TABLET, FILM COATED 50 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-2571 TABLET, FILM COATED 10 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 64125-133 TABLET, FILM COATED 10 mg ORAL ANDA 24 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 64125-134 TABLET, FILM COATED 25 mg ORAL ANDA 24 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 64125-135 TABLET, FILM COATED 50 mg ORAL ANDA 24 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 64380-169 TABLET 10 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 64380-170 TABLET 25 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 64380-171 TABLET 50 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67046-1564 TABLET, FILM COATED 25 mg ORAL ANDA 19 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68071-3669 TABLET 50 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68151-2768 TABLET 10 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68180-311 TABLET, FILM COATED 10 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68180-312 TABLET, FILM COATED 25 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68180-313 TABLET, FILM COATED 50 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 68180-314 CAPSULE 75 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 68180-315 CAPSULE 100 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 68180-316 CAPSULE 125 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 68180-317 CAPSULE 150 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 69315-133 TABLET, FILM COATED 10 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 69315-134 TABLET, FILM COATED 25 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 69315-135 TABLET, FILM COATED 50 mg ORAL ANDA 20 sections