CLOCAPRAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C28H37ClN4O
Molecular Weight	481.073
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1(CCN(CCCN2C3=CC=CC=C3CCC4=C2C=C(Cl)C=C4)CC1)N5CCCCC5

InChI

InChIKey=QAZKXHSIKKNOHH-UHFFFAOYSA-N

InChI=1S/C28H37ClN4O/c29-24-12-11-23-10-9-22-7-2-3-8-25(22)33(26(23)21-24)18-6-15-31-19-13-28(14-20-31,27(30)34)32-16-4-1-5-17-32/h2-3,7-8,11-12,21H,1,4-6,9-10,13-20H2,(H2,30,34)

HIDE SMILES / InChI

Description
Sources: https://medical.mt-pharma.co.jp/di/file/if/f_clo.pdf
Curator's Comment: description was created based on several sources, including: http://www.kegg.jp/medicus-bin/japic_med_product?id=00048317-003 | http://en.pharmacodia.com/web/drug/1_10640.html

Clocapramine is a chlorinated derivative of carpipramine. The hydrochloride has been given orally in the treatment of schizophrenia. Clocapramine is an antagonist of the Dopamine D2 and Serotonine (5-HT2) receptors. It has been implicated in at least one strange death, including a suicide. It augments the paroxetine in the panic disorder treatment.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7766287	Antagonist 2778	13.0 nM [Ki]
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8786644	Antagonist 2778	1.9 nM [Ki]
Dopamine D3 receptor 91 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8786644	Antagonist 2778	1.5 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00048317-003	Primary		Approved 8429	CLOFEKTON Approved Use Clofekton 10% is indicated for the treatment of schizophrenia. Launch Date 1974

PubMed

Title	Date	PubMed
A crossover study of clocapramine and haloperidol in chronic schizophrenia.	1985	4076529
Clocapramine-related fatality. Postmortem drug levels in multiple psychoactive drug poisoning.	2001 Oct 15	11587865
Atypical properties of several classes of antipsychotic drugs on the basis of differential induction of Fos-like immunoreactivity in the rat brain.	2004 Nov 26	15519367
Augmentation of paroxetine with clocapramine in panic disorder.	2007 Aug	17610675

Patents

Sample Use Guides

In Vivo Use Guide

30 to 150 mg daily in three divided doses

Route of Administration: Oral

In Vitro Use Guide

Various concentrations of clocapramine was applied to NCB20 cells and reward currents were recorded. The cells were voltage-clamped at -60 mV. The compositions of internal and external solutions were both normal. Concentration-response curves for each compound were obtained from 6 to 10 cell. The Hill coefficients of clocapramine was 0.79. The Ka values for these compounds was 1.1 uM.

Name

Type

Language

CLOCAPRAMINE

Official Name

English

clocapramine [INN]

Common Name

English

1'-(3-(3-CHLORO-10,11-DIHYDRO-5H-DIBENZ(B,F)AZEPIN-5-YL)PROPYL)(1,4'-BIPIPERIDINE)-4'-CARBOXAMIDE

Systematic Name

English

(1,4'-BIPIPERIDINE)-4'-CARBOXAMIDE, 1'-(3-(3-CHLORO-10,11-DIHYDRO-5H-DIBENZ(B,F)AZEPIN-5-YL)PROPYL)-

Systematic Name

English

CLOCAPRAMINE [MI]

Common Name

English

Clocapramine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265