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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 of BMS-908662

SMILES

COC(=O)NC1=NC2=C(N1)C=CC(=C2)C3(O)N(C(=O)C4=CC=CC=C34)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
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

PubMed

TitleDatePubMed
Paradoxical activation of T cells via augmented ERK signaling mediated by a RAF inhibitor.
2014 Jan
Phase I study of XL281 (BMS-908662), a potent oral RAF kinase inhibitor, in patients with advanced solid tumors.
2015 Apr
Clinico-morphological features of BRAF inhibition-induced proliferative skin lesions in cancer patients.
2015 Jan 1
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 Tue Oct 22 12:36:59 UTC 2019
Edited
by admin
on Tue Oct 22 12:36:59 UTC 2019
Record UNII
DW2NWI3TFN
Record Status Validated (UNII)
Record Version
  • Download
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
CAS
870603-16-0
Created by admin on Tue Oct 22 12:36:59 UTC 2019 , Edited by admin on Tue Oct 22 12:36:59 UTC 2019
PRIMARY
ChEMBL
CHEMBL3545027
Created by admin on Tue Oct 22 12:36:59 UTC 2019 , Edited by admin on Tue Oct 22 12:36:59 UTC 2019
PRIMARY
PUBCHEM
56931136
Created by admin on Tue Oct 22 12:36:59 UTC 2019 , Edited by admin on Tue Oct 22 12:36:59 UTC 2019
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY