General
Preferred name
IMIPRAMINE
Synonyms
IMIPRAMINE HYDROCHLORIDE ()
Prazepine ()
Tofranil-PM ()
Imipramine HCl ()
G 22355 ()
Tofranil ()
Melipramine ()
Imipramine (HCl) ()
Imipramine (hydrochloride) ()
IMIPRAMINE PAMOATE ()
Melipramine HCl,G 22355 ()
Imipramini hydrochloridum ()
Pramine ()
NSC-114900 ()
Presamine ()
Sarimp ()
Imipramine hydrochloride rs ()
Pryleugan ()
G-22355 ()
Praminil ()
Imizine ()
Imidobenzyle ()
Janimine ()
Berkomine ()
NSC-169866 ()
Sermonil ()
ORG-2463 ()
Antideprin ()
Cristalia ()
Trimipramine maleate impurity, imipramine- ()
Imipramine embonate ()
Imipramine (hydrochloride) ()
P&D ID
PD010016
CAS
113-52-0
50-49-7
10075-24-8
Tags
drug
nuisance
natural product
biased GPCR ligand
available
Approved by
FDA
First approval
1959
1973
Drug Status
approved
Drug indication
Depression
Antidepressant
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
INDICATION For the relief of symptoms of depression and as temporary adjunctive therapy in reducing enuresis in children aged 6 years and older [FDA Label]. ; ; May also be used off-label to manage panic disorders with or without agoraphobia, as a second line agent for ADHD in children and adolescents, to manage bulimia nervosa, for short-term management of acute depressive episodes in bipolar disorder and schizophrenia, for the treatment of acute stress disorder and posttraumatic stress disorder, and for symptomatic treatment of postherpetic neuralgia and painful diabetic neuropathy [L1349,L1348,A31900,L1351,L1352,L1353,A31904].
TOXICITY The anticholinergic actvity of imipramine can produce dry mucous membranes, blurred vision, increased intraocular pressure, hyperthermia, constipation, adynamic ileus, urinary retention, delayed micturition, and dilation of the urinary tract [L1360].; ; Central nervous system and neuromuscular effects include drowsiness, lethargy, fatigue, agitation, excitement, nightmares, restlessness, insomnia, confusion, disturbed concentration, disorientation, delusions, and hallucinations.; ; Effects on the GI tract include anorexia, nausea and vomiting, diarrhea, abdominal cramps, increases in pancreatic enzymes, epigastric distress, stomatitis, peculiar taste, and black tongue.; ; Rarely agranulocytosis, thrombocytopenia, eosinophilia, leukopenia, and purpura have occured.; ; Infants whose mothers were receiving tricyclic antidepressants prior to delivery have experienced cardiac problems, irritability, respiratory distress, muscle spasms, seizures, and urinary retention.; ; Serotonin syndrome can occur when used in conjunction with other pro-serotonergic drugs.; ; ### LD50 Values; Rat; - Oral 250 mg/kg; - Intraperitoneal 79mg/kg; - Subcutaneous 250 mg/kg; - Intravenous 15.9 mg/kg; ; Mouse ; - Oral 188 mg/kg; - Intraperitoneal 51.6 mg/kg; - Subcutaneous 195 μg/kg; - Intravenous 21 mg/kg; ; Human range of toxicity is considered to include single dosages greater than 5 mg/kg.
METABOLISM Imipramine is nearly exclusively metabolized by the liver [A31907]. Imipramine is converted to desipramine by CYP1A2, CYP3A4, CYP2C19. Both imipramine and desipramine are hydroxylated by CYP2D6 [A31915]. Desipramine is an active metabolite.; ; Minor metabolic pathways include dealkylation to form an imidodibenzyl product as well as demethylation of desipramine to didemethylimipramine and subsequent hydroxylation [A31907].; ; Less than 5% of orally administered imipramine is excreted unchanged.
DESCRIPTION Imipramine is a tricyclic antidepressant (TCA). (GtoPdb)
PHARMACODYNAMICS Imipramine is a tricyclic antidepressant with general pharmacological properties similar to those of structurally related tricyclic antidepressant drugs such as amitriptyline and doxepin. While it acts to block both, imipramine displays a much higher affinity for the serotonin reuptake transporter than for the norepinephrine reuptake transporter [A6584]. Imipramine produces effects similar to other monoamine targeting antidepressants, increasing serotonin- and norepinephrine-based neurotransmission.; ; This modulation of neurotransmission produces a complex range of changes in brain structure and function along with an improvement in depressive symptoms. The changes include increases in hippocampal neurogenesis and reduced downregulation of this neurogenesis in response to stress [A31931]. These implicate brain derived neurotrophic factor signalling as a necessary contributor to antidepressant effect although the link to the direct increase in monoamine neurotransmission is unclear.; ; Serotonin reuptake targeting agents may also produce a down-regulation in β-adrenergic receptors in the brain [A31938].
DESCRIPTION Tricyclic antidepressant; blocks reuptake of serotonin and norepinephrine (LOPAC library)
Cell lines
2
Organisms
4
Compound Sets
33
AdooQ Bioactive Compound Library
A13410
BiasDB
Imipramine
Cayman Chemical Bioactives
15890
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL1692
CHEMBL11
CHEMBL3989845
ChEMBL Drugs
CHEMBL1692
CHEMBL11
CHEMBL3989845
Drug Repurposing Hub
DrugBank
DB00458
DrugBank Approved Drugs
DB00458
DrugCentral
1427
DrugCentral Approved Drugs
1427
DrugMAP
DM2NUH3
DrugMAP Approved Drugs
DM2NUH3
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS100770
EUbOPEN Chemogenomics Library
Guide to Pharmacology
357
Ki Database
IMIPRAMINE
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL11
MedChem Express Bioactive Compound Library
HY-B1490
NCATS Inxight Approved Drugs
OGG85SX4E4
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Nuisance compounds in cellular assays
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
imipramine-hcl
TargetMol Bioactive Compound Library
T7941
The Spectrum Collection
External IDs
78
Properties
(calculated by RDKit )
Molecular Weight
280.19
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
0
Rotatable Bonds
4
Ring Count
3
Aromatic Ring Count
2
cLogP
3.88
TPSA
6.48
Fraction CSP3
0.37
Chiral centers
0.0
Largest ring
7.0
QED
0.84
Structural alerts
1
CAD
Nuisance compounds in cellular assays
Related compounds
Custom attributes
(extracted from source data)
Selectivity
Reuptake
MOA
norepinephrine transporter inhibitor
5-HT Reuptake Inhibitors
Sodium Channel Blockers
Norepinephrine Reuptake Inhibitors
norepinephrine reputake inhibitor, serotonin reuptake inhibitor
Target
Norepinephrine transporter
Serotonin Transporter
serotonin
ADRA1A, ADRA1B, ADRA1D, CHRM1, CHRM2, CHRM3, CHRM4, CHRM5, DRD1, DRD2, DRD5, HRH1, HTR1A, HTR2A, HTR2C, HTR6, HTR7, KCND2, KCND3, KCNH1, KCNH2, SLC6A2, SLC6A3, SLC6A4
5-HT Receptor,Serotonin Transporter
Pathway
Neuronal Signaling
Apoptosis
Autophagy
Member status
member
Indication
depression, nocturnal enuresis
Disease Area
neurology/psychiatry, urology
Therapeutic Class
Antidepressants
Source data