IBIPINABANT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H20Cl2N4O2S
Molecular Weight	487.402
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN\C(=N/S(=O)(=O)C1=CC=C(Cl)C=C1)N2C[C@@H](C(=N2)C3=CC=C(Cl)C=C3)C4=CC=CC=C4

InChI

InChIKey=AXJQVVLKUYCICH-OAQYLSRUSA-N

InChI=1S/C23H20Cl2N4O2S/c1-26-23(28-32(30,31)20-13-11-19(25)12-14-20)29-15-21(16-5-3-2-4-6-16)22(27-29)17-7-9-18(24)10-8-17/h2-14,21H,15H2,1H3,(H,26,28)/t21-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H20Cl2N4O2S
Molecular Weight	487.402
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800017654 | https://www.ncbi.nlm.nih.gov/pubmed/22821849 | https://medkoo.com/products/15543

Ibipinabant (IBI) is an orally active potent cannabinoid-1 receptor (CB1R) antagonist. This drug was studied for the treatment of obesity and psychotic disorders. However, the development of the drug was discontinued in November 2008. Now, ibipinabant is only used for laboratory research, especially structure-activity relationship studies into novel CB1 antagonists.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid receptor 1 30 Target ID: P21554\|\|\|Q5UB37 Gene ID: 1268.0 Gene Symbol: CNR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14736243	Antagonist 2778		25.2 nM [Ki]
Cannabinoid receptor 1 30 Target ID: P21554\|\|\|Q5UB37 Gene ID: 1268.0 Gene Symbol: CNR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14736243	Antagonist 2778

PubMed

Title	Date	PubMed
		252160389
Diaryl dihydropyrazole-3-carboxamides with significant in vivo antiobesity activity related to CB1 receptor antagonism: synthesis, biological evaluation, and molecular modeling in the homology model.	2007 Nov 29	17979261
Cannabinoid receptor antagonist-induced striated muscle toxicity and ethylmalonic-adipic aciduria in beagle dogs.	2012 Oct	22821849

Patents

Sample Use Guides

In Vivo Use Guide

5 mg (ST) to 50 mg (LT) Tablet, Oral, Once Daily, 12 weeks treatment followed by 20 week washout (ST); up to 190 weeks treatment (LT)

Route of Administration: Oral

In Vitro Use Guide

(±)-Ibipinabant ((±)-SLV319) is a potent and selective cannabinoid-1 (CB-1) receptor antagonist with an IC50 of 22 nM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:14:40 UTC 2023` Edited by `admin` on `Fri Dec 15 16:14:40 UTC 2023`
Record UNII	O5CSC6WH1T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IBIPINABANT

Official Name

English

BMS-646256

Code

English

(E)-(4S)-3-(4-CHLOROPHENYL)-N'-((4-CHLOROPHENYL)SULFONYL)-N-METHYL-4-PHENYL-4,5- DIHYDRO-1H-PYRAZOLE-1-CARBOXIMIDAMIDE

Systematic Name

English

Ibipinabant [WHO-DD]

Common Name

English

1H-PYRAZOLE-1-CARBOXIMIDAMIDE, 3-(4-CHLOROPHENYL)-N-((4-CHLOROPHENYL)SULFONYL)-4,5- DIHYDRO-N'-METHYL-4-PHENYL-, (4S)-

Systematic Name

English

IBIPINABANT [USAN]

Common Name

English

SLV-319

Code

English

ibipinabant [INN]

Common Name

English

Code System Code Type Description

DRUG BANK

DB12649