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
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
DescriptionSources: https://www.drugbank.ca/drugs/DB00458Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/087846s028,087844s027,087845s027lbl.pdf
Sources: https://www.drugbank.ca/drugs/DB00458
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
Sources: https://www.drugs.com/pro/imipramine.html
Curator's Comment: CNS active and penetrant http://onlinelibrary.wiley.com/doi/10.1016/S0009-9236(03)90534-0/abstract;jsessionid=0501D49064CCA6E885143C367F1535B3.f02t02
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25930134
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P27169 Gene ID: 5444.0 Gene Symbol: PON1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23001316 |
|||
Target ID: CHEMBL222 Sources: https://www.drugbank.ca/drugs/DB00458 |
12.0 nM [Ki] | ||
Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18983139 |
3.2 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Tofranil Approved UseTofranil 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 Date4.5394559E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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) Sources: 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) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 6 uM] | ||||
yes [Ki 182.9 uM] | ||||
yes [Ki 42 uM] | ||||
yes [Ki 42 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
The antinicotinic effects of drugs with clinically useful sedative-antianxiety properties. | 1975 |
|
[Behavior pharmacology of maprotiline, a new antidepressant]. | 1975 Nov |
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Biphasic effects of imipramine in experimental models of epilepsy. | 1976 Jun |
|
Pediatric cardiovascular effects of imipramine and desipramine. | 1991 Jan |
|
Painful ejaculation associated with antidepressants in four patients. | 1991 Nov |
|
Lithium and calcium channel blockers: possible neurotoxicity. | 1991 Sep 15 |
|
[Clinical-pharmacological case report: drug-induced inappropriate ADH secretion]. | 1992 Nov 17 |
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[Evaluation of analgesic action of fluvoxamine compared with efficacy of imipramine and tramadol for treatment of sciatica--open trial]. | 2002 |
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Effect of fluoxetine and imipramine on the pharmacokinetics and tolerability of the antipsychotic quetiapine. | 2002 Apr |
|
Adverse pulmonary vascular effects of high dose tricyclic antidepressants: acute and chronic animal studies. | 2002 Aug |
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Phenelzine treatment increases transcription factor AP-2 levels in rat brain. | 2003 Aug 28 |
|
Prescription of QT-prolonging drugs in a cohort of about 5 million outpatients. | 2003 Feb 1 |
|
N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases. | 2003 Nov |
|
Glutathione S-transferase pi as a target for tricyclic antidepressants in human brain. | 2004 |
|
[Hypnotherapy in the treatment of refractory nocturnal enuresis]. | 2004 Feb 19 |
|
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 |
|
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 |
|
Mechanism of block of hEag1 K+ channels by imipramine and astemizole. | 2004 Oct |
|
[Cardiac arrhythmia in amitriptyline poisoning in children]. | 2005 Apr-Jun |
|
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. | 2005 Feb |
|
Improved pharmacodynamics of timolol maleate from a mucoadhesive niosomal ophthalmic drug delivery system. | 2005 Feb 16 |
|
[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 |
|
QTc prolongation associated with combination therapy of levofloxacin, imipramine, and fluoxetine. | 2005 Mar |
|
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 |
|
[Chemico-toxicological analysis of haloperidol in blood with high-performance liquid chromatography in combined poisoning]. | 2007 May-Jun |
|
Gene expression profiling in rat liver treated with compounds inducing phospholipidosis. | 2008 Jun 15 |
|
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 |
|
Behavioral changes in rats induced by a dipeptidyl peptidase IV inhibitor methionyl-2(S)-cyanopyrrolidine: experimental model of anxiety-depression disorder. | 2009 Mar |
|
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 |
|
Imipramine enhances cell proliferation and decreases neurodegeneration in the hippocampus after transient global cerebral ischemia in rats. | 2010 Feb 5 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/imipramine.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23001316
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.
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Classification Tree | Code System | Code | ||
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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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1427
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C62039
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793
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OGG85SX4E4
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D007099
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SUB08152MIG
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200-042-1
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Imipramine
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169866
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DTXSID1043881
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3696
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CHEMBL11
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357
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OGG85SX4E4
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M6232
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5691
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IMIPRAMINE
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DB00458
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50-49-7
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47499
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3100
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)