LIFIRAFENIB

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NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H17F3N4O3
Molecular Weight	478.4227
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of LIFIRAFENIB

Structure Search

SMILES

[H][C@]12OC3=CC=C(OC4=CC=NC5=C4CCC(=O)N5)C=C3[C@@]1([H])[C@@H]2C6=NC7=C(N6)C=C(C=C7)C(F)(F)F

InChI

InChIKey=NGFFVZQXSRKHBM-FKBYEOEOSA-N

InChI=1S/C25H17F3N4O3/c26-25(27,28)11-1-4-15-16(9-11)31-24(30-15)21-20-14-10-12(2-5-17(14)35-22(20)21)34-18-7-8-29-23-13(18)3-6-19(33)32-23/h1-2,4-5,7-10,20-22H,3,6H2,(H,30,31)(H,29,32,33)/t20-,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H17F3N4O3
Molecular Weight	478.4227
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:57:20 UTC 2023` Edited by `admin` on `Sat Dec 16 11:57:20 UTC 2023`
Record UNII	8762XZS5ZF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LIFIRAFENIB

Official Name

English

5-(((1R,1AS,6BR)-1-(6-(TRIFLUOROMETHYL)-1H-BENZIMIDAZOL-2-YL)-1A,6B-DIHYDRO-1H-CYCLOPROPA(B)BENZOFURAN-5-YL)OXY)-3,4-DIHYDRO-1H-1,8-NAPHTHYRIDIN-2-ONE

Systematic Name

English

BGB-283

Code

English

LIFIRAFENIB [USAN]

Common Name

English

BEIGENE-283

Common Name

English

lifirafenib [INN]

Common Name

English

1,8-NAPHTHYRIDIN-2(1H)-ONE, 5-(((1R,1AS,6BR)-1A,6B-DIHYDRO-1-(6-(TRIFLUOROMETHYL)-1H-BENZIMIDAZOL-2-YL)-1H-CYCLOPROPA(B)BENZOFURAN-5-YL)OXY)-3,4-DIHYDRO-

Systematic Name

English

Lifirafenib [WHO-DD]

Common Name

English

Code System Code Type Description

NCI_THESAURUS

C124995

Created by admin on Sat Dec 16 11:57:20 UTC 2023 , Edited by admin on Sat Dec 16 11:57:20 UTC 2023

PRIMARY

PUBCHEM

89670174

Created by admin on Sat Dec 16 11:57:20 UTC 2023 , Edited by admin on Sat Dec 16 11:57:20 UTC 2023

PRIMARY

DRUG BANK

DB14773

Created by admin on Sat Dec 16 11:57:20 UTC 2023 , Edited by admin on Sat Dec 16 11:57:20 UTC 2023

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FDA UNII

8762XZS5ZF

Created by admin on Sat Dec 16 11:57:20 UTC 2023 , Edited by admin on Sat Dec 16 11:57:20 UTC 2023

PRIMARY

INN

10554

Created by admin on Sat Dec 16 11:57:20 UTC 2023 , Edited by admin on Sat Dec 16 11:57:20 UTC 2023

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USAN

FG-149

Created by admin on Sat Dec 16 11:57:20 UTC 2023 , Edited by admin on Sat Dec 16 11:57:20 UTC 2023

PRIMARY

CAS

1446090-79-4

Created by admin on Sat Dec 16 11:57:20 UTC 2023 , Edited by admin on Sat Dec 16 11:57:20 UTC 2023

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SMS_ID

300000034330

Created by admin on Sat Dec 16 11:57:20 UTC 2023 , Edited by admin on Sat Dec 16 11:57:20 UTC 2023

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MANUFACTURER PRODUCT INFORMATION

BEIGENE-283

Created by admin on Sat Dec 16 11:57:20 UTC 2023 , Edited by admin on Sat Dec 16 11:57:20 UTC 2023

PRIMARY

MedKoo CAT NO.: 206465, CAS NO.: 1446090-77-2Description: BGB-283 is a Novel potent and selective RAF Kinase and EGFR inhibitor. BGB-283-displays Potent Antitumor Activity in B-RAF Mutated Colorectal Cancers. In vitro, BGB-283 potently inhibits B-RAFV600E-activated ERK phosphorylation and cell proliferation. It demonstrates selective cytotoxicity and preferentially inhibits proliferation of cancer cells harbouring B-RAFV600E and EGFR mutation/amplification. In B-RAFV600E CRC cell lines, BGB-283 effectively inhibits the reactivation of EGFR and EGFR-mediated cell proliferation. In vivo, BGB-283 treatment leads to dose-dependent tumor growth inhibition accompanied by partial and complete tumor regressions in both cell-line derived and primary human colorectal tumor xenografts bearing B-RAFV600E mutation. BGB-283 as a potent antitumor drug candidate with clinical potential for treating CRC harbouring B-RAFV600E mutation. (last updated: 5/17/2016).

ChEMBL

CHEMBL3545246

Created by admin on Sat Dec 16 11:57:20 UTC 2023 , Edited by admin on Sat Dec 16 11:57:20 UTC 2023

PRIMARY

Related Record Type Details


					S54X4ZF5K5

SERINE/THREONINE-PROTEIN KINASE B-RAF

TARGET -> INHIBITOR

Amount:


					9VU33DC00T

LIFIRAFENIB MALEATE

SALT/SOLVATE -> PARENT

Related Record Type Details


					8762XZS5ZF

ACTIVE MOIETY

Comments:

Here, we report characterization of a dual RAF kinase/EGFR inhibitor, BGB-283, which is currently under clinical investigation. In vitro, BGB-283 potently inhibits BRAF(V600E)-activated ERK phosphorylation and cell proliferation. It demonstrates selective cytotoxicity and preferentially inhibits proliferation of cancer cells harboring BRAF(V600E) and EGFR mutation/amplification. In BRAF(V600E) colorectal cancer cell lines, BGB-283 effectively inhibits the reactivation of EGFR and EGFR-mediated cell proliferation. In vivo, BGB-283 treatment leads to dose-dependent tumor growth inhibition accompanied by partial and complete tumor regressions in both cell line-derived and primary human colorectal tumor xenografts bearing BRAF(V600E) mutation. These findings support BGB-283 as a potent antitumor drug candidate with clinical potential for treating colorectal cancer harboring BRAF(V600E) mutation.