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

Stem definitionDrug idCAS RN
substances of the imipramine group 812 50-47-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • desipramine
  • demethylimipramine
  • desimipramine
  • desipramin
  • desmethylimipramine
  • methylaminopropyliminodibenzyl
  • monodemethylimipramine
  • norimipramine
  • desipramine hydrochloride
  • desipramine HCl
A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.
  • Molecular weight: 266.39
  • Formula: C18H22N2
  • CLOGP: 4.47
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 15.27
  • ALOGS: -3.83
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.10 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 16.09 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 82.50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 15 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 11 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.16 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 22 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 20, 1964 FDA SANOFI AVENTIS US

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 325.05 87.48 65 100 20969 2336951
Toxicity to various agents 109.76 87.48 30 135 32724 2325196

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 118.29 71.36 27 66 16285 1730403

Pharmacologic Action:

SourceCodeDescription
ATC N06AA01 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:50949 serotonin uptake inhibitor
CHEBI has role CHEBI:48873 cholinergic antagonist
CHEBI has role CHEBI:37890 alpha-adrenergic antagonist
CHEBI has role CHEBI:37955 H1-receptor antagonist
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:88188 drug allergen
MeSH PA D000928 Antidepressive Agents
MeSH PA D000929 Antidepressive Agents, Tricyclic
MeSH PA D002491 Central Nervous System Agents
MeSH PA D004791 Enzyme Inhibitors
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
Depressive disorder indication 35489007
Cataplexy off-label use 46263000
Anxiety off-label use 48694002
Bulimia nervosa off-label use 78004001
Neuropathic pain off-label use 247398009
Chronic idiopathic urticaria off-label use 302162004
Panic disorder off-label use 371631005 DOID:594
Attention deficit hyperactivity disorder off-label use 406506008
Depressive Disorder following Traumatic Brain Injury off-label use
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Bipolar disorder contraindication 13746004 DOID:3312
Lowered convulsive threshold contraindication 19260006
Glaucoma contraindication 23986001 DOID:1686
Torsades de pointes contraindication 31722008
Hyperthyroidism contraindication 34486009 DOID:7998
Conduction disorder of the heart contraindication 44808001
Schizophrenia contraindication 58214004 DOID:5419
Epilepsy contraindication 84757009 DOID:1826
Kidney disease contraindication 90708001 DOID:557
Prolonged QT interval contraindication 111975006
Seizure disorder contraindication 128613002
Cerebrovascular accident contraindication 230690007
Disease of liver contraindication 235856003 DOID:409
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Myocardial infarction in recovery phase contraindication 418044006
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.83 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 9.08 WOMBAT-PK CHEMBL
D(2) dopamine receptor GPCR Ki 5.63 PDSP
5-hydroxytryptamine receptor 1A GPCR Ki 5.19 PDSP
Sodium-dependent dopamine transporter Transporter Ki 9.31 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.25 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.62 CHEMBL
Muscarinic acetylcholine receptor M5 GPCR Ki 6.84 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 7 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 6.80 WOMBAT-PK
Sodium-dependent serotonin transporter Transporter Kd 7.75 WOMBAT-PK
Voltage-dependent calcium channel gamma-1 subunit Ion channel WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR Ki 6.80 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 6.68 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 6.27 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 6.76 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR EC50 6.50 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR EC50 6.50 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 5.86 WOMBAT-PK
5-hydroxytryptamine receptor 1B GPCR Ki 6.97 PDSP
Alpha-2A adrenergic receptor GPCR Ki 5.86 PDSP
D(1A) dopamine receptor GPCR Ki 5.26 PDSP
Histamine H1 receptor GPCR Ki 7.12 WOMBAT-PK
Equilibrative nucleoside transporter 4 Transporter INHIBITOR Ki 4.49 IUPHAR
Sodium-dependent dopamine transporter Transporter Ki 5.19 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 6.79 CHEMBL
Transporter Transporter Ki 9.11 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 9.60 CHEMBL
Sodium-dependent noradrenaline transporter Transporter IC50 5.80 CHEMBL
Transporter Transporter Ki 9.19 CHEMBL
Sodium-dependent serotonin transporter Transporter IC50 5.03 CHEMBL
Histamine H1 receptor GPCR IC50 9.10 CHEMBL
Serotonin (5-HT) receptor GPCR IC50 6.46 CHEMBL
G protein-activated inward rectifier potassium channel 2 Ion channel BLOCKER IC50 4.40 IUPHAR
G protein-activated inward rectifier potassium channel 4 Unclassified BLOCKER IC50 4.30 IUPHAR

External reference:

IDSource
D003891 MESH_DESCRIPTOR_UI
4019708 VUID
N0000147800 NUI
C0011685 UMLSCUI
D00812 KEGG_DRUG
1Y58DO4MY1 UNII
58-28-6 SECONDARY_CAS_RN
33378002 SNOMEDCT_US
4019708 VANDF
004602 NDDF
3247 RXNORM
372705002 SNOMEDCT_US
d00145 MMSL
CHEBI:47781 CHEBI
CHEMBL72 ChEMBL_ID
CHEMBL1696 ChEMBL_ID
1500 INN_ID
DB01151 DRUGBANK_ID
2399 IUPHAR_LIGAND_ID
2995 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1971 TABLET, FILM COATED 10 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1972 TABLET, FILM COATED 25 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1973 TABLET, FILM COATED 50 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1974 TABLET, FILM COATED 75 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1975 TABLET, FILM COATED 100 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1976 TABLET, FILM COATED 150 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-5218 TABLET, FILM COATED 10 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-8218 TABLET, FILM COATED 10 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-8972 TABLET, FILM COATED 25 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-8973 TABLET, FILM COATED 50 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-8974 TABLET, FILM COATED 75 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-8975 TABLET, FILM COATED 100 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-8976 TABLET, FILM COATED 150 mg ORAL ANDA 14 sections
DESIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-586 TABLET, FILM COATED 100 mg ORAL ANDA 14 sections
DESIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-830 TABLET, FILM COATED 10 mg ORAL ANDA 14 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-428 TABLET, FILM COATED 25 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-845 TABLET 10 mg ORAL ANDA 11 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-578 TABLET 10 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-579 TABLET 25 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-580 TABLET 50 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-581 TABLET 75 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-582 TABLET 100 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-583 TABLET 150 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24724-067 TABLET 10 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24724-068 TABLET 25 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24724-069 TABLET 50 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24724-070 TABLET 75 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24724-071 TABLET 100 mg ORAL ANDA 13 sections
Desipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24724-072 TABLET 150 mg ORAL ANDA 13 sections
Norpramin HUMAN PRESCRIPTION DRUG LABEL 1 30698-007 TABLET, SUGAR COATED 10 mg ORAL NDA 14 sections