Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H26N2.C4H4O4 |
Molecular Weight | 410.5069 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(CN(C)C)CN1c2ccccc2CCc3ccccc31.C(\[H])(=C(\[H])/C(=O)O)/C(=O)O
InChI
InChIKey=YDGHCKHAXOUQOS-BTJKTKAUSA-N
InChI=1S/C20H26N2.C4H4O4/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22;5-3(6)1-2-4(7)8/h4-11,16H,12-15H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
Molecular Formula | C20H26N2 |
Molecular Weight | 294.4346 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0723 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Trimipramine is a tricyclic antidepressant similar to imipramine, but with more antihistaminic and sedative properties. It was sold under brand name surmontil for the relief of symptoms of depression. Endogenous depression is more likely to be alleviated than other depressive states. In studies with neurotic outpatients, the drug appeared to be equivalent to amitriptyline in the less-depressed patients but somewhat less effective than amitriptyline in the more severely depressed patients. In hospitalized depressed patients, trimipramine and imipramine were equally effective in relieving depression. Trimipramine has been reported to differ from other typical tricyclic antidepressant drugs in several aspects, for instance it does not inhibit neuronal transmitter uptake and does not cause down-regulation of beta-adrenoceptors. Moreover, it may possess antipsychotic activity in schizophrenic patients. In addition, was found that it did not antagonize the inhibitory effect of noradrenaline and 5-hydroxytryptamine on the release of transmitter, mediated by presynaptic auto receptors. In radioligand binding studies, trimipramine showed fairly high affinities for some dopamine (DA), noradrenaline and 5-hydroxytryptamine (5-HT) receptor subtypes (5-HT2 receptors = alpha 1A/B-adrenoceptors greater than or equal to D2 receptors), intermediate affinities for D1 receptors, alpha 2B-adrenoceptors and 5-HT1C receptors but only low affinities for alpha 2A-adrenoceptors, 5-HT1A, 5-HT1D and 5-HT3 receptors. It may thus be classified as an atypical neuroleptic drug.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1663593 |
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Target ID: CHEMBL2095200 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1663593 |
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Target ID: CHEMBL2096676 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1663593 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SURMONTIL Approved UseSURMONTIL is indicated for the relief of symptoms of depression. Endogenous depression is more likely to be alleviated than other depressive states. In studies with neurotic outpatients, the drug appeared to be equivalent to amitriptyline in the less-depressed patients but somewhat less effective than amitriptyline in the more severely depressed patients. In hospitalized depressed patients, trimipramine and imipramine were equally effective in relieving depression. Launch Date2.97993601E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
92.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14520122/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIMIPRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.13 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14520122/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIMIPRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
31 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14520122/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIMIPRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
yes [IC50 31 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
yes [Km 258 uM] | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
[Instead of benzodiazepines. An antidepressant as sleep aid]. | 2001 Jan 18 |
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Seizure during combination of trimipramine and bupropion. | 2001 Jun |
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Hydrophobia as a rare presentation of Cotard's syndrome: a case report. | 2002 Aug |
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Connection between lithium and muscular incoordination. | 2002 Feb |
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The effects of tricyclic antidepressants on breast cancer risk. | 2002 Jan 7 |
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[Delusional depression as differential dementia of the Alzheimer type diagnosis]. | 2002 May |
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Trimipramine in primary insomnia: results of a polysomnographic double-blind controlled study. | 2002 Sep |
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Effects of REM sleep awakenings and related wakening paradigms on the ultradian sleep cycle and the symptoms in depression. | 2002 Sep-Oct |
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Optimised procedures for the reversed-phase liquid chromatographic analysis of formulations containing tricyclic antidepressants. | 2003 Apr 24 |
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Analysis of eighteen antidepressants, four atypical antipsychotics and active metabolites in serum by liquid chromatography: a simple tool for therapeutic drug monitoring. | 2003 Aug 25 |
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Antipsychotic efficacy of the antidepressant trimipramine: a randomized, double-blind comparison with the phenothiazine perazine. | 2003 Mar-Apr |
|
A comparative solid-phase extraction study for the simultaneous determination of fluoxetine, amitriptyline, nortriptyline, trimipramine, maprotiline, clomipramine, and trazodone in whole blood by capillary gas-liquid chromatography with nitrogen-phosphorus detection. | 2003 Sep |
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Current use of selective serotonin reuptake inhibitors and risk of acute myocardial infarction. | 2004 |
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Intrathecal tri-cyclic antidepressants produce spinal anesthesia. | 2004 Nov |
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Risk of fetal exposure to tricyclic antidepressants. | 2004 Oct |
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Intravenous administration of the neuropeptide galanin has fast antidepressant efficacy and affects the sleep EEG. | 2004 Oct |
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Ghrelin plasma levels during psychopharmacological treatment. | 2005 |
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Antidepressants and their effect on sleep. | 2005 Dec |
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Protonation of trimipramine salts of maleate, mesylate and hydrochloride observed by 1H, 13C and 15N NMR spectroscopy. | 2005 Feb |
|
Depression and sleep: pathophysiology and treatment. | 2006 |
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[Effects of antidepressants on sleep]. | 2006 Apr 30 |
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[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 |
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Solid-phase extraction and analysis of 20 antidepressant drugs in human plasma by LC/MS with SSI method. | 2006 Oct 16 |
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Quantitative determination of forty-eight antidepressants and antipsychotics in human serum by HPLC tandem mass spectrometry: a multi-level, single-sample approach. | 2006 Oct 20 |
|
Tricyclic antidepressant poisoning: an evidence-based consensus guideline for out-of-hospital management. | 2007 |
|
Antidepressants for the treatment of insomnia : a suitable approach? | 2008 |
|
Pharmacokinetic genes do not influence response or tolerance to citalopram in the STAR*D sample. | 2008 Apr 2 |
|
Determination of tricyclic antidepressants in human plasma using pipette tip solid-phase extraction and gas chromatography-mass spectrometry. | 2008 Jul |
|
The clinical-familial correlates and naturalistic outcome of panic-disorder-agoraphobia with and without lifetime bipolar II comorbidity. | 2008 Nov 13 |
|
Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies. | 2008 Nov 4 |
|
Outcome in delusional depression comparing trimipramine monotherapy with a combination of amitriptyline and haloperidol--a double-blind multicenter trial. | 2009 Apr |
|
Efficacy of tricyclic antidepressants in irritable bowel syndrome: a meta-analysis. | 2009 Apr 7 |
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The effect of trimipramine on dream recall and dream emotions in depressive outpatients. | 2009 May 30 |
|
Accuracy of Veterans Affairs databases for diagnoses of chronic diseases. | 2009 Oct |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
Role of human UGT2B10 in N-glucuronidation of tricyclic antidepressants, amitriptyline, imipramine, clomipramine, and trimipramine. | 2010 May |
Sample Use Guides
Outpatients and Office Patients: initially, 75 mg/day in divided doses, increased to 150 mg/day. Dosages over 200 mg/day are not recommended. Maintenance therapy is in the range of 50 to 150 mg/day. For convenient therapy and to facilitate patient compliance, the total dosage requirement may be given at bedtime.
Hospitalized Patient: initially, 100 mg/day in divided doses. This may be increased gradually in a few days to 200 mg/day, depending upon individual response and tolerance. If improvement does not occur in 2 to 3 weeks, the dose may be increased to the maximum recommended dose of 250 to 300 mg/day.
Adolescent and Geriatric Patients: initially, a dose of 50 mg/day is recommended, with gradual increments up to 100 mg/day, depending upon patient response and tolerance.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21484238
It was investigated whether trimipramine and three of its metabolites interact with targets of other antidepressants, namely, the human monoamine transporters for noradrenaline (hNAT), serotonin (hSERT), and dopamine (hDAT), and with the human organic cation transporters (hOCT1, hOCT2, and hOCT3) which are expressed in the brain and are known to be involved in the uptake of monoamines. HEK293 cells heterologously expressing the abovementioned transporters were used to determine the inhibition of [(3)H]MPP(+) uptake by trimipramine and its main metabolites. At concentrations up to 30 μM, all transporters, except hOCT3, were inhibited by all examined substances. With IC(50) values between 2 and 10 μM, trimipramine inhibited hSERT, hNAT, hOCT1, and hOCT2, whereas clearly higher concentrations were needed for half-maximal inhibition of hDAT. Desmethyl-trimipramine showed about the same potencies as trimipramine, whereas 2-hydroxy-trimipramine was less potent at hNAT, hSERT, and hOCT1. Trimipramine-N-oxide preferentially inhibited hSERT.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:00:56 UTC 2021
by
admin
on
Fri Jun 25 21:00:56 UTC 2021
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Record UNII |
269K6498LD
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C94727
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521-78-8
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208-318-3
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1692709
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20230-75-5
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M11164
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SUB04977MIG
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71532
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DBSALT000969
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CHEMBL644
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1217260-65-5
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521-78-8
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C47773
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269K6498LD
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5282318
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Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |