BMS-908662

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C24H19ClN4O4
Molecular Weight	462.885
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)NC1=NC2=CC(=CC=C2N1)C3(O)N(C(=O)C4=C3C=CC=C4)C5=C(C)C=CC(Cl)=C5

InChI

InChIKey=MMNNTJYFHUDSKL-UHFFFAOYSA-N

InChI=1S/C24H19ClN4O4/c1-13-7-9-15(25)12-20(13)29-21(30)16-5-3-4-6-17(16)24(29,32)14-8-10-18-19(11-14)27-22(26-18)28-23(31)33-2/h3-12,32H,1-2H3,(H2,26,27,28,31)

HIDE SMILES / InChI

Molecular Formula	C24H19ClN4O4
Molecular Weight	462.885
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25476894 | https://news.bms.com/press-release/financial-news/bristol-myers-squibb-and-exelixis-enter-global-collaboration-two-novel-

BMS-908662 (previously known as XL281) is a small molecule Raf kinase inhibitor that lies immediately downstream of RAS and are key components of the RAS/RAF/MEK/ERK kinase-signaling pathway. Bristol-Myers Squibb has received an exclusive worldwide license to develop and commercialize antineoplastic agent XL281. BMS-908662 participated in phase I development for the treatment of patients with melanoma and in combination with cetuximab for patients with colorectal cancer. However, further, development has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Paradoxical activation of T cells via augmented ERK signaling mediated by a RAF inhibitor.	2014 Jan	24416731
Phase I study of XL281 (BMS-908662), a potent oral RAF kinase inhibitor, in patients with advanced solid tumors.	2015 Apr	25476894
Clinico-morphological features of BRAF inhibition-induced proliferative skin lesions in cancer patients.	2015 Jan 1	25186461

Patents

Sample Use Guides

In Vivo Use Guide

Capsules, Oral, escalating doses starting at 25 mg, every 12 hours (Q 12 h), Continuously

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:04:32 GMT 2023` Edited by `admin` on `Fri Dec 15 16:04:32 GMT 2023`
Record UNII	DW2NWI3TFN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BMS-908662

Common Name

English

CARBAMIC ACID, N-(6-(2-(5-CHLORO-2-METHYLPHENYL)-2,3-DIHYDRO-1-HYDROXY-3-OXO-1H-ISOINDOL-1-YL)-1H-BENZIMIDAZOL-2-YL)-, METHYL ESTER

Common Name

English

METHYL (5-(2-(5-CHLORO-2-METHYLPHENYL)-1-HYDROXY-3-OXO-2,3-DIHYDRO-1H-ISOINDOL-1-YL)-1H-BENZIMIDAZOL-2-YL)CARBAMATE

Systematic Name

English

CARBAMIC ACID, (5-(2-(5-CHLORO-2-METHYLPHENYL)-2,3-DIHYDRO-1-HYDRO

Common Name

English

(±)-METHYL (5-(2-(5-CHLORO-2-METHYLPHENYL)-1-HYDROXY-3-OXO-2,3-DIHYDRO-1H-ISOINDOL-1-YL)-1H-BENZIMIDAZOL-2-YL)CARBAMATE

Systematic Name

English

METHYL (5-(2-(5-CHLORO-2-METHYLPHENYL)-1-HYDROXY-3-OXO-2,3-DIHYDRO-1H-ISOINDOL-1-YL)-1H-BENZIMIDAZOL-2-YL)CARBAMATE, (±)-

Systematic Name

English

BMS-908662 FREE BASE

Common Name

English

XL 281 [WHO-DD]

Common Name

English

Code System Code Type Description

SMS_ID

100000174997