CLOMIPRAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H23ClN2
Molecular Weight	314.852
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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

Molecular Formula	C19H23ClN2
Molecular Weight	314.852
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019906s039lbl.pdf

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

Primary Target	Pharmacology	Condition	Potency
serotonin uptake 20 Target ID: GO:0051610 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019906s039lbl.pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obsessive-compulsive disorder 33 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019906s039lbl.pdf	Primary		Approved 8583	ANAFRANIL Approved Use Clomipramine hydrochloride capsules USP are indicated for the treatment of obsessions and compulsions in patients with Obsessive-Compulsive Disorder (OCD). Launch Date 1989

C_max

Value	Dose	Co-administered	Analyte	Population
92 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/019906s043lbl.pdf	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		CLOMIPRAMINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN
31.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8991493	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		CLOMIPRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
736 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8991493	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		CLOMIPRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
23.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8991493	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		CLOMIPRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

Doses

Dose	Population	Adverse events
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12404554/	unhealthy, 35 Health Status: unhealthy Age Group: 35 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12404554/	Other AEs: Dry mouth, Constipation... Other AEs: Dry mouth (42.9%) Constipation (25%) Somnolence (24.1%) Tremor (22.3%) Dizziness (17.9%) Nausea (16.1%) Sweating (13.4%) Asthenia (9.8%) Insomnia (8%) Abdominal pain (3.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/12404554/
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/019906s043lbl.pdf	unhealthy, Children and Adolescents Health Status: unhealthy Age Group: Children and Adolescents Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/019906s043lbl.pdf	Other AEs: Somnolence, Tremor... Other AEs: Somnolence (46%) Tremor (33%) Dizziness (41%) Headache (28%) Insomnia (11%) Nervousness (4%) Myoclonus (2%) Paresthesia (2%) Memory impairment (7%) Anxiety (2%) Twitching (4%) Hypertonia (2%) Sleep disorder (9%) Confusion (2%) Depersonalization (2%) Irritability (2%) Panic reaction (2%) Aggressive reaction (2%) Paresis (2%) Sweating increased (9%) Rash (4%) Pruritus (2%) Skin odor abnormal (2%) Dry mouth (63%) Constipation (22%) Nausea (9%) Dyspepsia (13%) Diarrhea (7%) Anorexia (22%) Abdominal pain (13%) Vomiting (7%) Eructation (2%) Ulcerative stomatitis (2%) Fatigue (35%) Weight increase (2%) Flushing (7%) Hot flushes (2%) Chest pain (7%) Fever (2%) Allergy (7%) Pain (4%) Weight decrease (7%) Otitis media (4%) Asthenia (2%) Halitosis (2%) Postural hypotension (4%) Palpitation (4%) Tachycardia (2%) Syncope (2%) Rhinitis (7%) Sinusitis (2%) Coughing (4%) Bronchospasm (7%) Dyspnea (2%) Laryngitis (2%) Micturition disorder (4%) Urinary retention (7%) Abnormal vision (7%) Taste perversion (4%) Tinnitus (4%) Anisocoria (2%) Blepharospasm (2%) Eye allergy (2%) Disorder vestibular (2%) Muscle weakness (2%) Anemia (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/019906s043lbl.pdf
250 mg 1 times / day multiple, oral Recommended Dose: 250 mg, 1 times / day Route: oral Route: multiple Dose: 250 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/019906s043lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/019906s043lbl.pdf	Other AEs: Somnolence, Tremor... Other AEs: Somnolence (54%) Tremor (54%) Dizziness (54%) Headache (52%) Insomnia (25%) Influence on libido (21%) Nervousness (18%) Myoclonus (13%) Increased appetite (11%) Paresthesia (9%) Memory impairment (9%) Anxiety (9%) Twitching (7%) Concentration impaired (5%) Depression (5%) Hypertonia (4%) Sleep disorder (4%) Psychosomatic disease (3%) Yawning (3%) Confusion (3%) Speech disorder (3%) Dreaming abnormal (3%) Agitation (3%) Migraine (3%) Depersonalization (2%) Irritability (2%) Emotional lability (2%) Panic reaction (1%) Sweating increased (29%) Rash (8%) Pruritus (6%) Dermatitis (2%) Acne (2%) Dry skin (2%) Urticaria (1%) Dry mouth (84%) Constipation (47%) Nausea (33%) Dyspepsia (22%) Diarrhea (13%) Anorexia (12%) Abdominal pain (11%) Vomiting (7%) Flatulence (6%) Tooth disorder (5%) Gastrointestinal disorder (2%) Dysphagia (2%) Esophagitis (1%) Fatigue (39%) Weight increase (18%) Flushing (8%) Hot flushes (5%) Chest pain (4%) Fever (4%) Allergy (3%) Pain (3%) Localised edema (2%) Chills (2%) Postural hypotension (6%) Palpitation (4%) Tachycardia (4%) Pharyngitis (14%) Rhinitis (12%) Sinusitis (6%) Coughing (6%) Bronchospasm (2%) Epistaxis (2%) Micturition disorder (14%) Urinary tract infection (6%) Micturition frequency (5%) Urinary retention (2%) Dysuria (2%) Cystitis (2%) Abnormal vision (18%) Taste perversion (8%) Tinnitus (6%) Lacrimation abnormal (3%) Mydriasis (2%) Conjunctivitis (1%) Myalgia (13%) Back pain (6%) Arthralgia (3%) Muscle weakness (1%) Purpura (3%) Thirst (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/019906s043lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 OCT1 620	CYP1A1 389 CYP1A2 1197 CYP2C8 810 CYP2C18 149 CYP2C19 1119 UGT2B10 131 UGT1A4 399

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18788725/	yes
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21718296/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT2B10 131	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20133892/	major
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20133892/	minor
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8667235/	no
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8667235/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8667235/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8667235/	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8667235/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8667235/	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8667235/ \| https://pubmed.ncbi.nlm.nih.gov/28470111/	yes	yes (pharmacogenomic study) Comment: administration of clomipramine to a CYP2C19 intermediate metabolizer resulted in elevated serum trough concentrations Sources: https://pubmed.ncbi.nlm.nih.gov/8667235/ \| https://pubmed.ncbi.nlm.nih.gov/28470111/
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8667235/ \| https://pubmed.ncbi.nlm.nih.gov/20531370/ \| https://pubmed.ncbi.nlm.nih.gov/28470111/	yes	yes (pharmacogenomic study) Comment: administration of clomipramine to a CYP2D6 intermediate metabolizer resulted in elevated serum trough concentrations Sources: https://pubmed.ncbi.nlm.nih.gov/8667235/ \| https://pubmed.ncbi.nlm.nih.gov/20531370/ \| https://pubmed.ncbi.nlm.nih.gov/28470111/

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/18634780/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:47780	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47780
ChemicalBook	CB5173107	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5173107
eMolecules	1883437	https://www.emolecules.com/cgi-bin/more?vid=1883437
MolPort	MolPort-002-051-949	https://www.molport.com/shop/molecule-link/MolPort-002-051-949
MolPort	MolPort-047-115-334	https://www.molport.com/shop/molecule-link/MolPort-047-115-334
ZINC	ZINC000000020248	http://zinc15.docking.org/substances/ZINC000000020248

PubMed

Title	Date	PubMed
Altered dendritic spine density in animal models of depression and in response to antidepressant treatment.	2001-12-01	11746712
Ping-pong gaze in combined intoxication with tranylcypromine, thioridazine, and clomipramine.	2001-11-29	11725219
Effects of clomipramine on Trypanosoma cruzi infection in mice.	2001-11-15	11706667
[Tricyclic antidepressants dosage and depressed elderly inpatients: a retrospective pharmaco-epidemiologic study].	2001-11-01	11686060
[Narcolepsy in a prepubertal boy].	2001-11	11725521
Antidepressants enhance glucocorticoid receptor function in vitro by modulating the membrane steroid transporters.	2001-11	11704655
Adults with early-onset obsessive-compulsive disorder.	2001-11	11691698
Antidepressant drug treatments induce glial cell line-derived neurotrophic factor (GDNF) synthesis and release in rat C6 glioblastoma cells.	2001-10	11595754
Clinical predictors of drug response in obsessive-compulsive disorder.	2001-10	11593074
Clomipramine discontinuation-emergent dystonia.	2001-10	11551294
Obsessive-compulsive symptoms during treatment with clozapine in a patient with schizophrenia.	2001-10	11551293
High-performance liquid chromatographic method to screen and quantitate seven selective serotonin reuptake inhibitors in human serum.	2001-09-25	11587344
HPLC of basic drugs on microparticulate strong cation-exchange materials - a review.	2001-09-15	11516893
Differential time-course profiles of dopamine release and uptake changes induced by three dopamine uptake inhibitors.	2001-09-15	11494401
Diurnal profile of melatonin secretion in the acute phase of major depression and in remission.	2001-09-06	11535940
Spontaneous reports on drug-induced pancreatitis in Denmark from 1968 to 1999.	2001-09	11699619
Effectiveness of pharmacotherapy for body dysmorphic disorder: a chart-review study.	2001-09	11681769
[Chronic discomfort with dentures - successful treatment with clomipramine].	2001-09	11678084
Taijin kyofusho: a form of social anxiety disorder that responds to serotonin reuptake inhibitors?	2001-09	11602029
Comment: serotonin syndrome and 5-HT2A antagonism.	2001-09	11573872
Antagonism of nicotinic acetylcholine receptors by inhibitors of monoamine uptake.	2001-09	11526465
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.	2001-09	11522320
Digitalis intoxication misdiagnosed as depression--revisited.	2001-08-10	11496033
Pharmacotherapy for severe aggression in a child with autism: "open label" evaluation of multiple medications on response frequency and intensity of behavioral intervention.	2001-08-10	11494958
[Value of fluoxetine in obsessive-compulsive disorder in the adult: review of the literature].	2001-08-08	11488259
Neurobiology and clinical pharmacology of obsessive-compulsive disorder.	2001-08-02	11479390
Interaction of psychotropic drugs with monoamine oxidase in rat brain.	2001-08	11518022
Neuroendocrine serotonergic and dopaminergic responsivity in male schizophrenic patients during treatment with neuroleptics and after switch to risperidone.	2001-08	11512043
Serum levels and cardiovascular effects of tricyclic antidepressants and selective serotonin reuptake inhibitors in depressed patients.	2001-08	11477329
Clomipramine versus haloperidol in the treatment of autistic disorder: a double-blind, placebo-controlled, crossover study.	2001-08	11476129
S33005, a novel ligand at both serotonin and norepinephrine transporters: II. Behavioral profile in comparison with venlafaxine, reboxetine, citalopram, and clomipramine.	2001-08	11454919
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.	2001-08	11454918
The critical window of brain development from susceptive to insusceptive. Effects of clomipramine neonatal treatment on sexual behavior.	2001-07-23	11454417
Clomipramine--beyond separation anxiety.	2001-07-14	11450830
Long-term follow-up and predictors of clinical outcome in obsessive-compulsive patients treated with serotonin reuptake inhibitors and behavioral therapy.	2001-07	11488364
Severe, refractory hypotension during anesthesia in a patient on chronic clomipramine therapy.	2001-07	11465569
A single blind comparison of amisulpride, fluoxetine and clomipramine in the treatment of restricting anorectics.	2001-07	11444677
Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines.	2001-06	11525844
Pharmacological manipulations of the extinction process of fear-induced ultrasonic vocalization in rats.	2001-06	11459003
Diurnal profile of melatonin concentrations in patients with major depression: relationship to the clinical manifestation and antidepressant treatment.	2001-06	11449197
Development of a depersonalization severity scale.	2001-04	11469161
Trichotillomania. Presentation, etiology, diagnosis and therapy.	2001	11721651
A review of the pharmacological and clinical profile of mirtazapine.	2001	11607047
Availability of learned helplessness test as a model of depression compared to a forced swimming test in rats.	2001	11598420
Vasopressin-dependent flank marking in golden hamsters is suppressed by drugs used in the treatment of obsessive-compulsive disorder.	2001	11545675
Smoking in patients receiving psychotropic medications: a pharmacokinetic perspective.	2001	11524025
Pharmacological characterization of the serotonin transporter in young and elderly subjects.	2001	11490175
Psychogenic excoriation. Clinical features, proposed diagnostic criteria, epidemiology and approaches to treatment.	2001	11475941
Tianeptine: a review of its use in depressive disorders.	2001	11463130
Depressive reactions in the course of clomipramine therapy used in the treatment of obsessional conditions.	1975	1154013

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:34:29 GMT 2025` Edited by `admin` on `Mon Mar 31 17:34:29 GMT 2025`
Record UNII	NUV44L116D
Record Status	`Validated (UNII)`
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Name

Type

Language

CLOMICALM

Preferred Name

English

CLOMIPRAMINE

Official Name

English

Clomipramine [WHO-DD]

Common Name

English

NSC-169865

Code

English

CHLORIMIPRAMINE

Common Name

English

CLOMIPRAMINE [MI]

Common Name

English

ANAPRAMINE

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

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