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

Details

Stereochemistry ACHIRAL
Molecular Formula C19H23ClN2
Molecular Weight 314.852
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOMIPRAMINE

SMILES

CN(C)CCCN1C2=CC=CC=C2CCC3=C1C=C(Cl)C=C3

InChI

InChIKey=GDLIGKIOYRNHDA-UHFFFAOYSA-N
InChI=1S/C19H23ClN2/c1-21(2)12-5-13-22-18-7-4-3-6-15(18)8-9-16-10-11-17(20)14-19(16)22/h3-4,6-7,10-11,14H,5,8-9,12-13H2,1-2H3

HIDE SMILES / InChI

Description

Clomipramine is an antidepressant drug which was approved by FDA for the treatment of Obsessive-Compulsive Disorder. The exact mechanism of its action is unknown, however it is supposed that it may exert its effect by inhibiting serotonin reuptake.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Depressive reactions in the course of clomipramine therapy used in the treatment of obsessional conditions.
1975
Availability of learned helplessness test as a model of depression compared to a forced swimming test in rats.
2001
Vasopressin-dependent flank marking in golden hamsters is suppressed by drugs used in the treatment of obsessive-compulsive disorder.
2001
Smoking in patients receiving psychotropic medications: a pharmacokinetic perspective.
2001
Pharmacological characterization of the serotonin transporter in young and elderly subjects.
2001
Long-term effects of tricyclic antidepressants on norepinephrine kinetics in humans.
2001
[A case of 'hallucination of soliloquy' with hypothyroidism induced Hashimoto disease. Meaning of psychopathological research about symptomatic psychosis].
2001
Compulsive checking behavior of quinpirole-sensitized rats as an animal model of Obsessive-Compulsive Disorder(OCD): form and control.
2001
Simultaneous analysis of clozapine, clomipramine and their metabolites by reversed-phase liquid chromatography.
2001 Apr
Use of clomipramine in treatment of obsessive-compulsive disorder, separation anxiety and noise phobia in dogs: a preliminary, clinical study.
2001 Apr
[Current drug treatment. Effects of antidepressive agents in nervous and stress-related disorders].
2001 Apr 2
Interaction of psychotropic drugs with monoamine oxidase in rat brain.
2001 Aug
Neuroendocrine serotonergic and dopaminergic responsivity in male schizophrenic patients during treatment with neuroleptics and after switch to risperidone.
2001 Aug
Serum levels and cardiovascular effects of tricyclic antidepressants and selective serotonin reuptake inhibitors in depressed patients.
2001 Aug
S33005, a novel ligand at both serotonin and norepinephrine transporters: II. Behavioral profile in comparison with venlafaxine, reboxetine, citalopram, and clomipramine.
2001 Aug
S33005, a novel ligand at both serotonin and norepinephrine transporters: I. Receptor binding, electrophysiological, and neurochemical profile in comparison with venlafaxine, reboxetine, citalopram, and clomipramine.
2001 Aug
Altered dendritic spine density in animal models of depression and in response to antidepressant treatment.
2001 Dec 1
A review of the pharmacological and clinical profile of mirtazapine.
2001 Fall
Assessment of as needed use of pharmacotherapy and the pause-squeeze technique in premature ejaculation.
2001 Feb
Long-term follow-up and predictors of clinical outcome in obsessive-compulsive patients treated with serotonin reuptake inhibitors and behavioral therapy.
2001 Jul
Severe, refractory hypotension during anesthesia in a patient on chronic clomipramine therapy.
2001 Jul
Pharmacological characterization and visualization of the glial serotonin transporter.
2001 Jul
Neurobiology and clinical pharmacology of obsessive-compulsive disorder.
2001 Jul-Aug
Clomipramine--beyond separation anxiety.
2001 Jul-Aug
Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines.
2001 Jun
Placebo affects the performance of rats in models of depression: is it a good control for behavioral experiments?
2001 Jun
Comparison of peripheral inhibitory effects of clomipramine with selective serotonin re-uptake inhibitors on contraction of vas deferens: in vitro and in vivo studies.
2001 Jun
The serotonergic 5-HT(2C) agonist m-chlorophenylpiperazine increases weight-supported locomotion without development of tolerance in rats with spinal transections.
2001 Jun
The exploding head syndrome.
2001 Jun
Cortical 5-HT(1A) receptor downregulation by antidepressants in rat brain.
2001 Jun
Pharmacological treatment of childhood obsessive-compulsive disorder: from theory to practice.
2001 Mar
Possible mild serotonin syndrome related to co-prescription of tandospirone and trazodone.
2001 Mar-Apr
Olanzapine augmentation of serotonin uptake inhibitors in obsessive-compulsive disorder: an open study.
2001 May
A meta-analysis of the efficacy and tolerability of paroxetine versus tricyclic antidepressants in the treatment of major depression.
2001 May
[A classic antidepressant as an analgesic. Chronic pain under secure control].
2001 May 28
[Value of fluoxetine in obsessive-compulsive disorder in the adult: review of the literature].
2001 May-Jun
Antidepressants enhance glucocorticoid receptor function in vitro by modulating the membrane steroid transporters.
2001 Nov
Antidepressant drug treatments induce glial cell line-derived neurotrophic factor (GDNF) synthesis and release in rat C6 glioblastoma cells.
2001 Oct
Clinical predictors of drug response in obsessive-compulsive disorder.
2001 Oct
Clomipramine discontinuation-emergent dystonia.
2001 Oct
Obsessive-compulsive symptoms during treatment with clozapine in a patient with schizophrenia.
2001 Oct
Ping-pong gaze in combined intoxication with tranylcypromine, thioridazine, and clomipramine.
2001 Oct-Dec
Spontaneous reports on drug-induced pancreatitis in Denmark from 1968 to 1999.
2001 Sep
[Chronic discomfort with dentures - successful treatment with clomipramine].
2001 Sep
Taijin kyofusho: a form of social anxiety disorder that responds to serotonin reuptake inhibitors?
2001 Sep
Antagonism of nicotinic acetylcholine receptors by inhibitors of monoamine uptake.
2001 Sep
Repeated but not acute clomipramine decreases the effect of N-methyl-D-aspartate receptor activation on serotonergic transmission between the raphe nuclei and frontal cortex.
2001 Sep
HPLC of basic drugs on microparticulate strong cation-exchange materials - a review.
2001 Sep 15
High-performance liquid chromatographic method to screen and quantitate seven selective serotonin reuptake inhibitors in human serum.
2001 Sep 25
Diurnal profile of melatonin secretion in the acute phase of major depression and in remission.
2001 Sep-Oct
Patents

Sample Use Guides

In Vivo Use Guide
Adults: Treatment should be initiated at a dosage of 25 mg daily and gradually increased, as tolerated, to approximately 100 mg during the first 2 weeks. During initial titration, the drug should be given in divided doses with meals to reduce gastrointestinal side effects. Thereafter, the dosage may be increased gradually over the next several weeks, up to a maximum of 250 mg daily.
Route of Administration: Oral
In Vitro Use Guide
The effect of clomipramine, at concentrations of 10(-7)M to 10(-4)M, was studied in vitro on the uptake of 5-hydroxytryptamine and dopamine uptake in human platelet-rich plasma.
Name Type Language
CLOMIPRAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NSC-169865
Code English
CHLORIMIPRAMINE
Common Name English
CLOMIPRAMINE [MI]
Common Name English
ANAPRAMINE
Common Name English
CLOMIPRAMINE [WHO-DD]
Common Name English
CLOMIPRAMINE [INN]
Common Name English
3-CHLORO-5-(3-(DIMETHYLAMINO)PROPYL)-10,11-DIHYDRO-5H-DIBENZ(B,F)AZEPINE
Systematic Name English
5H-DIBENZ(B,F)AZEPINE-5-PROPANAMINE, 3-CHLORO-10,11-DIHYDRO-N,N-DIMETHYL-
Systematic Name English
CLOMICALM
Brand Name English
3-CHLORO-IMINODIBENZYL
Common Name English
CLOMIPRAMINE [HSDB]
Common Name English
CLOMIPRAMINE [VANDF]
Common Name English
CLOMIPRAMINE [EMA EPAR: VETERINARY]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 24.4
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
NDF-RT N0000175752
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
WHO-ATC N06AA04
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
CFR 21 CFR 520.455
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
NCI_THESAURUS C94727
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
EMA VETERINARY ASSESSMENT REPORTS CLOMICALM (AUTHORISED)
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
WHO-VATC QN06AA04
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
LIVERTOX 223
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C61608
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
LactMed
303-49-1
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
RXCUI
2597
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY RxNorm
EPA CompTox
303-49-1
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
EVMPD
SUB06725MIG
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
ChEMBL
CHEMBL415
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
INN
2238
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
MERCK INDEX
M3648
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
CLOMIPRAMINE
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
MESH
D002997
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
DRUG BANK
DB01242
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
HSDB
303-49-1
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
ECHA (EC/EINECS)
206-144-2
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
PUBCHEM
2801
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
IUPHAR
2398
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY
CAS
303-49-1
Created by admin on Tue Oct 22 00:38:39 UTC 2019 , Edited by admin on Tue Oct 22 00:38:39 UTC 2019
PRIMARY