U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H24N2.ClH
Molecular Weight 316.8688
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMIPRAMINE HYDROCHLORIDE

SMILES

CN(C)CCCN1c2ccccc2CCc3ccccc31.Cl

InChI

InChIKey=XZZXIYZZBJDEEP-UHFFFAOYSA-N
InChI=1S/C19H24N2.ClH/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21;/h3-6,8-11H,7,12-15H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula C19H24N2
Molecular Weight 280.408
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/087846s028,087844s027,087845s027lbl.pdf

Imipramine is a tricyclic antidepressant with general pharmacological properties similar to those of structurally related tricyclic antidepressant drugs such as amitriptyline and doxepin. A tertiary amine, imipramine inhibits the reuptake of serotonin more so than most secondary amine tricyclics, meaning that it blocks the reuptake of neurotransmitters serotonin and noradrenaline almost equally. With chronic use, imipramine also down-regulates cerebral cortical β-adrenergic receptors and sensitizes post-synaptic sertonergic receptors, which also contributes to increased serotonergic transmission. It takes approximately 2 - 4 weeks for antidepressants effects to occur. The onset of action may be longer, up to 8 weeks, in some individuals. It is also effective in migraine prophylaxis, but not in abortion of acute migraine attack. Imipramine works by inhibiting the neuronal reuptake of the neurotransmitters norepinephrine and serotonin. It binds the sodium-dependent serotonin transporter and sodium-dependent norepinephrine transporter preventing or reducing the reuptake of norepinephrine and serotonin by nerve cells. Depression has been linked to a lack of stimulation of the post-synaptic neuron by norepinephrine and serotonin. Slowing the reuptake of these neurotransmitters increases their concentration in the synaptic cleft, which is thought to contribute to relieving symptoms of depression. In addition to acutely inhibiting neurotransmitter re-uptake, imipramine causes down-regulation of cerebral cortical beta-adrenergic receptors and sensitization of post-synaptic serotonergic receptors with chronic use. This leads to enhanced serotonergic transmission. Used for relief of symptoms of depression and as temporary adjunctive therapy in reducing enuresis in children aged 6 years and older. May also be used to manage panic disorders, with or without agoraphobia, as a second line agent in ADHD, management of eating disorders, for short-term management of acute depressive episodes in bipolar disorder and schizophrenia, and for symptomatic treatment of postherpetic neuralgia.

CNS Activity

Curator's Comment:: CNS active and penetrant http://onlinelibrary.wiley.com/doi/10.1016/S0009-9236(03)90534-0/abstract;jsessionid=0501D49064CCA6E885143C367F1535B3.f02t02

Originator

Curator's Comment:: Roland Kuhn, Swiss psychiatrist, discovered the therapeutic affect of imipramine in depression in 1957 http://www.cinp.org/wp-content/uploads/2015/06/history1.pdf

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P27169
Gene ID: 5444.0
Gene Symbol: PON1
Target Organism: Homo sapiens (Human)
12.0 nM [Ki]
3.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Tofranil

Approved Use

Tofranil is used for: Treating depression. It is also used in some children to help reduce bedwetting. It may also be used for other conditions as determined by your doctor.

Launch Date

4.5394559E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
107 μg/L
130 mg 1 times / day steady-state, oral
dose: 130 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Desipramine
IMIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
24.5 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
427 ng × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12 h
130 mg 1 times / day steady-state, oral
dose: 130 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Desipramine
IMIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
21.1 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
22%
130 mg 1 times / day steady-state, oral
dose: 130 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Desipramine
IMIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
200 mg/day 1 times / day steady, oral
Dose: 200 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 200 mg/day, 1 times / day
Sources:
unhealthy, 18-70 years
n = 82
Health Status: unhealthy
Condition: major depression | melancholia
Age Group: 18-70 years
Population Size: 82
Sources:
Disc. AE: Nausea...
AEs leading to
discontinuation/dose reduction:
Nausea (1 patient)
Sources:
25 mg/day 1 times / day steady, oral
Dose: 25 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 25 mg/day, 1 times / day
Sources:
unhealthy, 42.6 ± 12.4 years
n = 59
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: 42.6 ± 12.4 years
Sex: M+F
Population Size: 59
Sources:
Disc. AE: Sleep disturbance, Urinary tract signs and symptoms NEC...
AEs leading to
discontinuation/dose reduction:
Sleep disturbance (3 patients)
Urinary tract signs and symptoms NEC (2 patients)
Palpitations (2 patients)
Anxiety (1 patient)
Dry mouth (1 patient)
Dizziness (3 patients)
Flushing (1 patient)
Constipation (1 patient)
Sources:
75 mg/day 1 times / day steady, oral (starting)
Recommended
Dose: 75 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 75 mg/day, 1 times / day
Sources:
unhealthy, < 24 years
Health Status: unhealthy
Condition: depression
Age Group: < 24 years
Sources:
Disc. AE: Suicidal ideation...
AEs leading to
discontinuation/dose reduction:
Suicidal ideation (grade 5)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nausea 1 patient
Disc. AE
200 mg/day 1 times / day steady, oral
Dose: 200 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 200 mg/day, 1 times / day
Sources:
unhealthy, 18-70 years
n = 82
Health Status: unhealthy
Condition: major depression | melancholia
Age Group: 18-70 years
Population Size: 82
Sources:
Anxiety 1 patient
Disc. AE
25 mg/day 1 times / day steady, oral
Dose: 25 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 25 mg/day, 1 times / day
Sources:
unhealthy, 42.6 ± 12.4 years
n = 59
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: 42.6 ± 12.4 years
Sex: M+F
Population Size: 59
Sources:
Constipation 1 patient
Disc. AE
25 mg/day 1 times / day steady, oral
Dose: 25 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 25 mg/day, 1 times / day
Sources:
unhealthy, 42.6 ± 12.4 years
n = 59
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: 42.6 ± 12.4 years
Sex: M+F
Population Size: 59
Sources:
Dry mouth 1 patient
Disc. AE
25 mg/day 1 times / day steady, oral
Dose: 25 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 25 mg/day, 1 times / day
Sources:
unhealthy, 42.6 ± 12.4 years
n = 59
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: 42.6 ± 12.4 years
Sex: M+F
Population Size: 59
Sources:
Flushing 1 patient
Disc. AE
25 mg/day 1 times / day steady, oral
Dose: 25 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 25 mg/day, 1 times / day
Sources:
unhealthy, 42.6 ± 12.4 years
n = 59
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: 42.6 ± 12.4 years
Sex: M+F
Population Size: 59
Sources:
Palpitations 2 patients
Disc. AE
25 mg/day 1 times / day steady, oral
Dose: 25 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 25 mg/day, 1 times / day
Sources:
unhealthy, 42.6 ± 12.4 years
n = 59
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: 42.6 ± 12.4 years
Sex: M+F
Population Size: 59
Sources:
Urinary tract signs and symptoms NEC 2 patients
Disc. AE
25 mg/day 1 times / day steady, oral
Dose: 25 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 25 mg/day, 1 times / day
Sources:
unhealthy, 42.6 ± 12.4 years
n = 59
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: 42.6 ± 12.4 years
Sex: M+F
Population Size: 59
Sources:
Dizziness 3 patients
Disc. AE
25 mg/day 1 times / day steady, oral
Dose: 25 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 25 mg/day, 1 times / day
Sources:
unhealthy, 42.6 ± 12.4 years
n = 59
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: 42.6 ± 12.4 years
Sex: M+F
Population Size: 59
Sources:
Sleep disturbance 3 patients
Disc. AE
25 mg/day 1 times / day steady, oral
Dose: 25 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 25 mg/day, 1 times / day
Sources:
unhealthy, 42.6 ± 12.4 years
n = 59
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: 42.6 ± 12.4 years
Sex: M+F
Population Size: 59
Sources:
Suicidal ideation grade 5
Disc. AE
75 mg/day 1 times / day steady, oral (starting)
Recommended
Dose: 75 mg/day, 1 times / day
Route: oral
Route: steady
Dose: 75 mg/day, 1 times / day
Sources:
unhealthy, < 24 years
Health Status: unhealthy
Condition: depression
Age Group: < 24 years
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​

Drug as perpetrator​

Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
The antinicotinic effects of drugs with clinically useful sedative-antianxiety properties.
1975
Biphasic effects of imipramine in experimental models of epilepsy.
1976 Jun
Imipramine-induced syndrome of inappropriate antidiuretic hormone secretion.
1991 Dec
Pediatric cardiovascular effects of imipramine and desipramine.
1991 Jan
Rabbit syndrome, antidepressant use, and cerebral perfusion SPECT scan findings.
1991 Nov
Painful ejaculation associated with antidepressants in four patients.
1991 Nov
Lithium and calcium channel blockers: possible neurotoxicity.
1991 Sep 15
[Cardiac arrhythmia in amitriptyline poisoning in children].
2005 Apr-Jun
[Influence of chronic melipramine administration abolition on locomotion and defensive conditioned reflexes in passive and active avoidance in rats].
2005 Jan-Feb
Roles for C16-ceramide and sphingosine 1-phosphate in regulating hepatocyte apoptosis in response to tumor necrosis factor-alpha.
2005 Jul 29
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Organophosphorothionate pesticides inhibit the bioactivation of imipramine by human hepatic cytochrome P450s.
2005 Jun 15
Exacerbation of harmaline-induced tremor by imipramine.
2005 May
UDP-glucuronosyltransferase 1A4 polymorphisms in a Japanese population and kinetics of clozapine glucuronidation.
2005 May
[Treatment of anxiety syndrome. A systematic literature review. Summary and conclusions by the SBU].
2005 Nov 21-27
The role of serendipity in drug discovery.
2006
Induction of neuroserpin expression in rat frontal cortex after chronic antidepressant treatment and electroconvulsive treatment.
2006 Feb
[Lack of antidepresant-like activity of some ligands of polyamine binding sites of NMDA receptors in models of depression].
2006 Jan-Feb
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Frequency of high-risk use of QT-prolonging medications.
2006 Jun
Antidepressant drugs activate SREBP and up-regulate cholesterol and fatty acid biosynthesis in human glial cells.
2006 Mar 13
Molecular identification and functional characterization of rat multidrug and toxin extrusion type transporter 1 as an organic cation/H+ antiporter in the kidney.
2006 Nov
Mechanism of imipramine-induced seizures in amygdala-kindled rats.
2006 Nov
Recurrence of dilated cardiomyopathy after re-introduction of a tricyclic antidepressant.
2006 Oct
Polypharmacy and EPS in a child; a case report.
2007
Influence of antidepressants on hemostasis.
2007
Curcumin reverses impaired hippocampal neurogenesis and increases serotonin receptor 1A mRNA and brain-derived neurotrophic factor expression in chronically stressed rats.
2007 Aug 8
[Chemico-toxicological analysis of haloperidol in blood with high-performance liquid chromatography in combined poisoning].
2007 May-Jun
Histone deacetylase 5 epigenetically controls behavioral adaptations to chronic emotional stimuli.
2007 Nov 8
In vitro detection of drug-induced phospholipidosis using gene expression and fluorescent phospholipid based methodologies.
2007 Sep
Hereditary diffuse gastric cancer: association with lobular breast cancer.
2008
Manifestation of psychiatric behaviors in a mouse model of griseofulvin-induced hepatic porphyria.
2008 Dec
Temporal expression of brain-derived neurotrophic factor (BDNF) mRNA in the rat hippocampus after treatment with selective and mixed monoaminergic antidepressants.
2008 Jan 14
D-161, a novel pyran-based triple monoamine transporter blocker: behavioral pharmacological evidence for antidepressant-like action.
2008 Jul 28
Pharmacological separation of hEAG and hERG K+ channel function in the human mammary carcinoma cell line MCF-7.
2008 Jun
Gene expression profiling in rat liver treated with compounds inducing phospholipidosis.
2008 Jun 15
[Chronic imipramine treatment normalizes decreased sexual motivation and high predisposition to catalepsy induced by propylthiouracil in rat].
2008 Mar-Apr
Chronic coadministration of carbamazepine together with imipramine produces antidepressant-like effects in an ACTH-induced animal model of treatment-resistant depression: involvement of 5-HT(2A) receptors?
2008 May
Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies.
2008 Nov 4
Sub-chronic administration of rimonabant causes loss of antidepressive activity and decreases doublecortin immunoreactivity in the mouse hippocampus.
2009 Dec 25
Suppressive effect of imipramine on vincristine-induced mechanical allodynia in mice.
2009 Jul
Possible role of trazodone and imipramine in sleep deprivation-induced anxiety-like behavior and oxidative damage in mice.
2009 Jul-Aug
Behavioral changes in rats induced by a dipeptidyl peptidase IV inhibitor methionyl-2(S)-cyanopyrrolidine: experimental model of anxiety-depression disorder.
2009 Mar
Chronic administration of imipramine normalizes decreased sexual motivation and increased predisposition to catalepsy induced by propylthiouracil in rats.
2009 May
Neurogenesis-dependent and -independent effects of fluoxetine in an animal model of anxiety/depression.
2009 May 28
A new homogeneous high-throughput screening assay for profiling compound activity on the human ether-a-go-go-related gene channel.
2009 Nov 1
Medicine and psychiatry in Western culture: Ancient Greek myths and modern prejudices.
2009 Oct 7
Imipramine enhances cell proliferation and decreases neurodegeneration in the hippocampus after transient global cerebral ischemia in rats.
2010 Feb 5
Prediction of phospholipidosis-inducing potential of drugs by in vitro biochemical and physicochemical assays followed by multivariate analysis.
2010 Mar
Hormonal responses to the 5-HT1A agonist buspirone in remitted endogenous depressive patients after long-term imipramine treatment.
2010 May
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Depression Tablets: Initial dose: 100 mg orally per day Maintenance dose: 100 to 200 mg orally per day (If no response after 2 weeks, increase to 250 to 300 mg per day) Maximum dose: 300 mg orally per day
Route of Administration: Oral
The inhibition percentage of human PON1 for imipramine was 15.6% at 100 ug/L after incubation for 1 h). At 350 ug/L, the inhibition percentage for imipramine 19.2% after 1 h and 20.2% after 2 h.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:59:38 UTC 2021
Edited
by admin
on Fri Jun 25 20:59:38 UTC 2021
Record UNII
BKE5Q1J60U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IMIPRAMINE HYDROCHLORIDE
EP   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
IMIPRAMINE HYDROCHLORIDE [USP-RS]
Common Name English
IMIPRAMINE HYDROCHLORIDE [MI]
Common Name English
IMIZINE
Common Name English
IMIDOBENZYLE
Common Name English
TOFRANIL
Common Name English
IMIPRAMINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
IMIPRAMINE HYDROCHLORIDE [MART.]
Common Name English
NSC-114900
Code English
PRAMINE
Brand Name English
PRYLEUGAN
Common Name English
PRESAMINE
Brand Name English
5-(3-(DIMETHYLAMINO)PROPYL)-10,11-DIHYDRO-5H-DIBENZ(B,F)AZEPINE MONOHYDROCHLORIDE
Systematic Name English
IMIPRAMINE HCL
Common Name English
JANIMINE
Brand Name English
IMIPRAMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
IMIPRAMINE HYDROCHLORIDE [VANDF]
Common Name English
IMIPRAMINE HYDROCHLORIDE [WHO-DD]
Common Name English
IMIPRAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
5H-DIBENZ(B,F)AZEPINE-5-PROPANAMINE, 10,11-DIHYDRO-N,N-DIMETHYL-, MONOHYDROCHLORIDE
Common Name English
IMIPRAMINE HYDROCHLORIDE RS [USP]
Common Name English
IMIPRAMINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
G-22355
Code English
IMIPRAMINE HYDROCHLORIDE [WHO-IP]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C94727
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
204-030-7
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY
MERCK INDEX
M6232
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY Merck Index
EPA CompTox
113-52-0
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY
ChEMBL
CHEMBL11
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY
EVMPD
SUB02644MIG
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY
USP_CATALOG
1338007
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY USP-RS
CAS
113-52-0
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY
DRUG BANK
DBSALT000099
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY
NCI_THESAURUS
C29116
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY
PUBCHEM
8228
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY
FDA UNII
BKE5Q1J60U
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
IMIPRAMINE HYDROCHLORIDE
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY Description: A white or slightly yellowish, crystalline powder; odourless or almost odourless. Solubility: Freely soluble in water, ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Psychotherapeutic drug. Storage: Imipramine hydrochloride should be kept in a tightly closed container, protected from light. Additional information: Even in the absence of light, Imipramine hydrochloride is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures.Requirement: Imipramine hydrochloride contains not less than 98.0% and not more than the equivalent of 102.0% of C19H24N2,HCl, calculated with reference to the dried substance.
RXCUI
150816
Created by admin on Fri Jun 25 20:59:38 UTC 2021 , Edited by admin on Fri Jun 25 20:59:38 UTC 2021
PRIMARY RxNorm
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