Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H24N2 |
| Molecular Weight | 280.408 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCCN1c2ccccc2CCc3ccccc31
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
| 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 |
DescriptionCurator's Comment:: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/087846s028,087844s027,087845s027lbl.pdf
Curator's Comment:: 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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P27169 Gene ID: 5444 Gene Symbol: PON1 Target Organism: Homo sapiens (Human) |
|||
Target ID: CHEMBL222 |
12 nM [Ki] | ||
Target ID: CHEMBL228 |
3.20000000000000018 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 Date453945600000 |
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 |
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 Health Status: unhealthy Age Group: 42.6 ± 12.4 years Sex: M+F 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 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 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 |
| 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 Health Status: unhealthy Age Group: 42.6 ± 12.4 years Sex: M+F 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 Health Status: unhealthy Age Group: 42.6 ± 12.4 years Sex: M+F 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 Health Status: unhealthy Age Group: 42.6 ± 12.4 years Sex: M+F 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 Health Status: unhealthy Age Group: 42.6 ± 12.4 years Sex: M+F 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 Health Status: unhealthy Age Group: 42.6 ± 12.4 years Sex: M+F 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 Health Status: unhealthy Age Group: 42.6 ± 12.4 years Sex: M+F 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 Health Status: unhealthy Age Group: 42.6 ± 12.4 years Sex: M+F 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 Health Status: unhealthy Age Group: 42.6 ± 12.4 years Sex: M+F Sources: |
| Suicidal ideation | grade 5 Disc. AE |
75 mg/day 1 times / day steady, oral 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 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 15:52:56 UTC 2021
by
admin
on
Sat Jun 26 15:52:56 UTC 2021
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| Record UNII |
OGG85SX4E4
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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WHO-VATC |
QN06AA02
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LIVERTOX |
502
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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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50-49-7
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3696
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CHEMBL11
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357
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M6232
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PRIMARY | Merck Index | ||
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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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3100
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| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
|
SALT/SOLVATE -> PARENT | |||
|
|
SALT/SOLVATE -> PARENT | |||
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> INHIBITOR | |||
|
METABOLIC ENZYME -> SUBSTRATE |
Metabolizing reaction by CYP2D6: 2-Hydroxylation
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
10%-20% OF TOTAL METABOLISM
|
||
|
|
BINDING PROTEIN->LIGAND | |||
|
TARGET -> INHIBITOR | |||
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> INHIBITOR | |||
|
TARGET -> INHIBITOR | |||
|
BINDER->LIGAND |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLITE ACTIVE -> PARENT |
Imipramine has activities at both the serotonin and norepeinephrine transporters with greater affinity for the serotonin transporter while desipramine and 2-hydroxydesipramine have greater affinities for the norepinephrine transporter (Owens et al., 1997).
|
||
|
METABOLITE ACTIVE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
