imipramine ๐Ÿถ Veterinary Use | 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 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

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
Paranoia 59.92 17.99 23 3132 10325 50591644
Completed suicide 54.30 17.99 53 3102 131836 50470133
Hallucination, auditory 52.12 17.99 21 3134 10707 50591262
Psychotic disorder 43.48 17.99 23 3132 21789 50580180
Toxicity to various agents 41.21 17.99 58 3097 212441 50389528
Stress cardiomyopathy 36.79 17.99 15 3140 7872 50594097
Urinary hesitation 21.23 17.99 7 3148 2022 50599947
Procedural hypotension 20.89 17.99 6 3149 1096 50600873
Limb mass 19.33 17.99 7 3148 2668 50599301

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 58.09 30.61 58 1530 173603 29399336
Blepharospasm 57.78 30.61 13 1575 1042 29571897
Completed suicide 51.82 30.61 41 1547 90205 29482734
Long QT syndrome 47.95 30.61 13 1575 2245 29570694
Pyelitis 42.96 30.61 7 1581 97 29572842
Neuroleptic malignant syndrome 40.63 30.61 19 1569 16129 29556810
Dystonia 39.32 30.61 16 1572 9733 29563206
Trismus 38.21 30.61 11 1577 2362 29570577
Muscle rigidity 33.07 30.61 14 1574 9397 29563542

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 93.21 17.33 93 4174 224321 64270144
Toxicity to various agents 60.16 17.33 95 4172 363418 64131047
Paranoia 57.82 17.33 26 4241 16326 64478139
Neuroleptic malignant syndrome 55.81 17.33 29 4238 24967 64469498
Overdose 43.29 17.33 53 4214 159513 64334952
Hallucination, auditory 41.71 17.33 21 4246 16918 64477547
Blepharospasm 40.08 17.33 13 4254 3362 64491103
Psychotic disorder 34.76 17.33 24 4243 34554 64459911
Long QT syndrome 34.73 17.33 13 4254 5126 64489339
Pyelitis 34.35 17.33 7 4260 282 64494183
Stress cardiomyopathy 33.61 17.33 15 4252 9242 64485223
Dystonia 28.68 17.33 17 4250 18848 64475617
Trismus 28.10 17.33 11 4256 4890 64489575
Respiratory depression 22.92 17.33 16 4251 23427 64471038
Muscle rigidity 22.09 17.33 14 4253 17459 64477006
Electrocardiogram QT prolonged 20.87 17.33 26 4241 79422 64415043
Suicide attempt 19.89 17.33 24 4243 70983 64423482
Parkinsonism 19.39 17.33 12 4255 14361 64480104
Withdrawal syndrome 18.35 17.33 14 4253 23478 64470987
Limb mass 18.10 17.33 7 4260 3014 64491451
Speech disorder 18.05 17.33 19 4248 48422 64446043
Electrocardiogram abnormal 17.54 17.33 11 4256 13470 64480995
Fluid intake reduced 17.52 17.33 8 4259 5192 64489273
Procedural hypotension 17.37 17.33 6 4261 1880 64492585

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N06AA02 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Non-selective monoamine reuptake inhibitors
MeSH PA D018663 Adrenergic Agents
MeSH PA D018759 Adrenergic Uptake Inhibitors
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
CHEBI has role CHEBI:35469 antidepressants
FDA EPC N0000175752 Tricyclic Antidepressant
CHEBI has role CHEBI:35640 adrenergic uptake inhibitors
CHEBI has role CHEBI:76779 post-proline endopeptidase inhibitors

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




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 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 2 Ion channel IC50 5.90 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
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
D(2) dopamine receptor GPCR Ki 6.17 WOMBAT-PK
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.28 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 Unclassified 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

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 Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1762 TABLET, FILM COATED 10 mg ORAL ANDA 19 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1764 TABLET, FILM COATED 25 mg ORAL ANDA 19 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1766 TABLET, FILM COATED 50 mg ORAL ANDA 19 sections
IMIPRAMINE PAMOATE HUMAN PRESCRIPTION DRUG LABEL 1 16590-963 CAPSULE 75 mg ORAL NDA 22 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-345 TABLET, FILM COATED 10 mg ORAL ANDA 24 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-346 TABLET, FILM COATED 25 mg ORAL ANDA 24 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-347 TABLET, FILM COATED 50 mg ORAL ANDA 24 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 49884-054 TABLET 10 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 49884-055 TABLET 25 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 49884-056 TABLET 50 mg ORAL ANDA 20 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 51655-455 TABLET, FILM COATED 50 mg ORAL ANDA 12 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 55289-144 TABLET, FILM COATED 25 mg ORAL ANDA 19 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55700-709 TABLET, FILM COATED 10 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55700-710 TABLET, FILM COATED 25 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 57297-314 CAPSULE 75 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 57297-315 CAPSULE 100 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 57297-316 CAPSULE 125 mg ORAL ANDA 20 sections
Imipramine Pamoate HUMAN PRESCRIPTION DRUG LABEL 1 57297-317 CAPSULE 150 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-095 TABLET 10 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-095 TABLET 10 mg ORAL ANDA 20 sections
Imipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-096 TABLET 25 mg ORAL ANDA 20 sections