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

Details

Stereochemistry ACHIRAL
Molecular Formula C19H24N2
Molecular Weight 280.4073
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMIPRAMINE

SMILES

CN(C)CCCN1C2=C(CCC3=C1C=CC=C3)C=CC=C2

InChI

InChIKey=BCGWQEUPMDMJNV-UHFFFAOYSA-N
InChI=1S/C19H24N2/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

HIDE SMILES / InChI

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

1984
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
Lithium and calcium channel blockers: possible neurotoxicity.
1991 Sep 15
Glutathione S-transferase pi as a target for tricyclic antidepressants in human brain.
2004
Serotonergic platelet markers of suicidal behavior--do they really exist?
2004 Apr
Effect of anxiolytic, antidepressant, and antipsychotic drugs on cocaine-induced seizures and mortality.
2004 Dec
Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels.
2004 Jul
Three year naturalistic outcome study of panic disorder patients treated with paroxetine.
2004 Jun 11
Eugenol exhibits antidepressant-like activity in mice and induces expression of metallothionein-III in the hippocampus.
2004 Jun 18
Long-term imipramine withdrawal induces a depressive-like behaviour in the forced swimming test.
2004 May 10
Influence of St John's wort on catecholamine turnover and cardiovascular regulation in humans.
2004 Nov
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
[Effect of acute melipramine administration on motor activity and defensive conditioned reflexes of passive and active avoidance in rats].
2004 Nov-Dec
Mechanism of block of hEag1 K+ channels by imipramine and astemizole.
2004 Oct
Inhibition of G protein-activated inwardly rectifying K+ channels by various antidepressant drugs.
2004 Oct
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system.
2005 Feb
[Influence of chronic melipramine administration abolition on locomotion and defensive conditioned reflexes in passive and active avoidance in rats].
2005 Jan-Feb
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
QTc prolongation associated with combination therapy of levofloxacin, imipramine, and fluoxetine.
2005 Mar
Serotonin (5HT), fluoxetine, imipramine and dopamine target distinct 5HT receptor signaling to modulate Caenorhabditis elegans egg-laying behavior.
2005 Mar
[Treatment of anxiety syndrome. A systematic literature review. Summary and conclusions by the SBU].
2005 Nov 21-27
[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
Mechanism of imipramine-induced seizures in amygdala-kindled rats.
2006 Nov
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
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
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
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.
Name Type Language
IMIPRAMINE
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
MELIPRAMINE
Common Name English
IMIPRAMINE [HSDB]
Common Name English
CLOMIPRAMINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
Common Name English
SERMONIL
Common Name English
IMIPRAMINE [MI]
Common Name English
imipramine [INN]
Common Name English
IMIPRAMINE [VANDF]
Common Name English
CRISTALIA
Common Name English
TRIMIPRAMINE MALEATE IMPURITY D [EP IMPURITY]
Common Name English
5-(3-(DIMETHYLAMINO)PROPYL)-10,11-DIHYDRO-5H-DIBENZ(B,F)AZEPINE
Systematic Name English
N-(.GAMMA.-DIMETHYLAMINOPROPYL)IMINODIBENZYL
Common Name English
BERKOMINE
Common Name English
ORG-2463
Code English
IMIPRAMINE [MART.]
Common Name English
ANTIDEPRIN
Common Name English
5H-DIBENZ(B,F)AZEPINE-5-PROPANAMINE, 10,11-DIHYDRO-N,N-DIMETHYL-
Systematic Name English
NSC-169866
Code English
TRIMIPRAMINE MALEATE IMPURITY, IMIPRAMINE- [USP IMPURITY]
Common Name English
Imipramine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QN06AA02
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LIVERTOX NBK547884
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WHO-ATC N06AA02
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NCI_THESAURUS C94727
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NDF-RT N0000175752
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Code System Code Type Description
DRUG CENTRAL
1427
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PRIMARY
NCI_THESAURUS
C62039
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PRIMARY
INN
793
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PRIMARY
FDA UNII
OGG85SX4E4
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PRIMARY
MESH
D007099
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PRIMARY
EVMPD
SUB08152MIG
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PRIMARY
ECHA (EC/EINECS)
200-042-1
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PRIMARY
LACTMED
Imipramine
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PRIMARY
NSC
169866
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PRIMARY
EPA CompTox
DTXSID1043881
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PRIMARY
PUBCHEM
3696
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PRIMARY
ChEMBL
CHEMBL11
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PRIMARY
IUPHAR
357
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PRIMARY
DAILYMED
OGG85SX4E4
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PRIMARY
MERCK INDEX
m6232
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PRIMARY Merck Index
RXCUI
5691
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PRIMARY RxNorm
WIKIPEDIA
IMIPRAMINE
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PRIMARY
DRUG BANK
DB00458
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PRIMARY
CAS
50-49-7
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PRIMARY
SMS_ID
100000083920
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PRIMARY
CHEBI
47499
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PRIMARY
HSDB
3100
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PRIMARY