Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H26N2 |
Molecular Weight | 294.4338 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(CN(C)C)CN1C2=C(CCC3=C1C=CC=C3)C=CC=C2
InChI
InChIKey=ZSCDBOWYZJWBIY-UHFFFAOYSA-N
InChI=1S/C20H26N2/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/h4-11,16H,12-15H2,1-3H3
Molecular Formula | C20H26N2 |
Molecular Weight | 294.4338 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
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Seizure during combination of trimipramine and bupropion. | 2001 Jun |
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Polysomnographic effects of adjuvant ginkgo biloba therapy in patients with major depression medicated with trimipramine. | 2001 Mar |
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Perazine for schizophrenia. | 2002 |
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Enantiomers' potential in psychopharmacology--a critical analysis with special emphasis on the antidepressant escitalopram. | 2002 Oct |
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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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Therapeutic drug monitoring of 13 antidepressant and five neuroleptic drugs in serum with liquid chromatography-electrospray ionization mass spectrometry. | 2003 Dec |
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Trimipramine pharmacokinetics after intravenous and oral administration in carriers of CYP2D6 genotypes predicting poor, extensive and ultrahigh activity. | 2003 Dec |
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Tricyclic antidepressants as long-acting local anesthetics. | 2003 May |
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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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Sleep disturbances, psychiatric disorders, and psychotropic drugs. | 2005 |
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Contribution of sleep research to the development of new antidepressants. | 2005 |
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The AGNP-TDM Expert Group Consensus Guidelines: focus on therapeutic monitoring of antidepressants. | 2005 |
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Automated determination of ziprasidone by HPLC with column switching and spectrophotometric detection. | 2005 Apr |
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Antidepressants and their effect on sleep. | 2005 Dec |
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[Multiple fibromas in systemic mastocytosis]. | 2005 May |
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Galactorrhea during treatment with trimipramine. A case report. | 2005 Nov |
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Depression and sleep: pathophysiology and treatment. | 2006 |
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Use of antidepressant medications in relation to the incidence of breast cancer. | 2006 Apr 10 |
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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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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 |
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Antidepressant therapy in tinnitus. | 2007 Apr |
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Differential neurotoxicity of tricyclic antidepressants and novel derivatives in vitro in a dorsal root ganglion cell culture model. | 2007 Aug |
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Shifts in metabolic parameters surrounding glucose homoeostasis resulting from tricyclic antidepressant therapy: implications of insulin resistance? | 2007 Jan |
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Heart rate variability reveals risk of arrhythmias after intoxication with antidepressants. | 2007 Jan |
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Quantification of tricyclic antidepressants and monoamine oxidase inhibitors by high-performance liquid chromatography-tandem mass spectrometry in whole blood. | 2007 May |
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Antidepressant interactions with the NMDA NR1-1b subunit. | 2008 |
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Antidepressants for the treatment of insomnia : a suitable approach? | 2008 |
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Metabolism in adipose tissue in response to citalopram and trimipramine treatment--an in situ microdialysis study. | 2008 Jun |
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Frequency of different anti-depressants associated with suicides and drug deaths. | 2008 Mar |
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Depression following thrombotic cardiovascular events in elderly medicare beneficiaries: risk of morbidity and mortality. | 2009 |
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Efficacy of tricyclic antidepressants in irritable bowel syndrome: a meta-analysis. | 2009 Apr 7 |
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Different mechanisms are involved in apoptosis induced by melanoma gangliosides on human monocyte-derived dendritic cells. | 2009 Jun |
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Antiulcer activity of fluvoxamine in rats and its effect on oxidant and antioxidant parameters in stomach tissue. | 2009 May 20 |
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The effect of trimipramine on dream recall and dream emotions in depressive outpatients. | 2009 May 30 |
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Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
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Interaction of the human plasma membrane monoamine transporter (hPMAT) with antidepressants and antipsychotics. | 2010 Jan |
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Modulatory effects of neuropsychopharmaca on intracellular pH of hippocampal neurones in vitro. | 2010 Jan 1 |
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Acid sphingomyelinase inhibitors normalize pulmonary ceramide and inflammation in cystic fibrosis. | 2010 Jun |
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Seizure risk associated with neuroactive drugs: data from the WHO adverse drug reactions database. | 2010 Mar |
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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
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Thu Jul 06 01:10:10 UTC 2023
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Thu Jul 06 01:10:10 UTC 2023
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Record UNII |
6S082C9NDT
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Record Status |
Validated (UNII)
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NDF-RT |
N0000175752
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WHO-ATC |
N06AA06
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QN06AA06
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NCI_THESAURUS |
C94727
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LIVERTOX |
NBK547855
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SUB11314MIG
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10834
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C61990
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2758
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Trimipramine
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M11164
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TRIMIPRAMINE
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CHEMBL644
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METABOLITE -> PARENT |
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