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

SMILES

CN(C)CCCN1C2=CC(Cl)=CC=C2CCC3=C1C=CC=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	MOL RATIO 1 MOL RATIO (average)

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

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

Primary Target	Pharmacology	Condition	Potency
serotonin uptake 20	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obsessive-compulsive disorder 28	Primary		Approved 8,429	ANAFRANIL

C_max

Value	Dose	Co-administered	Analyte	Population
92 ng/mL	50 mg single, oral		CLOMIPRAMINE plasma	Homo sapiens
31.3 ng/mL	50 mg single, oral		CLOMIPRAMINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
736 ng × h/mL	50 mg single, oral		CLOMIPRAMINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
23.5 h	50 mg single, oral		CLOMIPRAMINE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
300 mg 1 times / day multiple, oral Recommended	unhealthy, 35	Other AEs: Dry mouth, Constipation...
200 mg 1 times / day multiple, oral Recommended	unhealthy, Children and Adolescents	Other AEs: Somnolence, Tremor...
250 mg 1 times / day multiple, oral Recommended	unhealthy, adult	Other AEs: Somnolence, Tremor...

Showing 1 to 3 of 3 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Sweating	13.4%	300 mg 1 times / day multiple, oral Recommended	unhealthy, 35
Nausea	16.1%	300 mg 1 times / day multiple, oral Recommended	unhealthy, 35
Dizziness	17.9%	300 mg 1 times / day multiple, oral Recommended	unhealthy, 35
Tremor	22.3%	300 mg 1 times / day multiple, oral Recommended	unhealthy, 35
Somnolence	24.1%	300 mg 1 times / day multiple, oral Recommended	unhealthy, 35

Showing 1 to 5 of 161 entries

Previous1 2 3 4 5…33Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	substrate 1,037	substrate 1,217	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,461 OCT1 512	CYP1A1 349 CYP1A2 1,054 CYP2C8 693 CYP2C18 138 CYP2C19 991 UGT2B10 127 UGT1A4 347

Drug as perpetrator

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 543	inhibitor 3,277	yes
P-gp 1,650	inhibitor 3,277	yes

Showing 1 to 2 of 2 entries

Previous1Next

Drug as victim

Show entries

Target	Modality	Activity
UGT2B10 127	substrate 3,367	major
UGT1A4 347	substrate 3,367	minor
CYP1A1 349	substrate 3,367	no
CYP2C18 138	substrate 3,367	no
CYP2C8 693	substrate 3,367	no

Showing 1 to 5 of 10 entries

Previous1 2Next

Tox targets

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

Showing 1 to 1 of 1 entries

Previous1Next

Sourcing

Sourcing

Show entries

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

Showing 1 to 5 of 6 entries

Previous1 2Next

PubMed

Show entries

Title	Date	PubMed
[Neuropsychiatric symptoms in preventive antimalarial treatment with mefloquine: apropos of 2 cases].	2000 Jul-Aug	11064842
Availability of learned helplessness test as a model of depression compared to a forced swimming test in rats.	2001	11598420
Pharmacological characterization of the serotonin transporter in young and elderly subjects.	2001	11490175
Selected tricyclic antidepressant ingestions involving children 6 years old or less.	2001 Feb	11157289
PET neuroimaging of clomipramine challenge in humans: focus on the thalamus.	2001 Feb 16	11172763

Showing 1 to 5 of 14 entries

Previous1 2 3Next

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.