LIFIRAFENIB MALEATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C25H17F3N4O3.3C4H4O4
Molecular Weight	1305.0619
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.FC(F)(F)C1=CC2=C(C=C1)N=C(N2)[C@@H]3[C@H]4OC5=C(C=C(OC6=C7CCC(=O)NC7=NC=C6)C=C5)[C@@H]34.FC(F)(F)C8=CC9=C(C=C8)N=C(N9)[C@@H]%10[C@H]%11OC%12=C(C=C(OC%13=C%14CCC(=O)NC%14=NC=C%13)C=C%12)[C@@H]%10%11

InChI

InChIKey=CETNPISTLYWCDC-SWWFIDOGSA-N

InChI=1S/2C25H17F3N4O3.3C4H4O4/c2*26-25(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;3*5-3(6)1-2-4(7)8/h2*1-2,4-5,7-10,20-22H,3,6H2,(H,30,31)(H,29,32,33);3*1-2H,(H,5,6)(H,7,8)/b;;3*2-1-/t2*20-,21-,22-;;;/m00.../s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30599278 | https://www.beigene.com/science-and-product-portfolio/pipeline/lifirafenib

Lifirafenib (BGB-283 or BEIGENE-283), a dual inhibitor targeting BRAF kinase and EGFR, was studied for the treatment of different cancer types harboring mutations in BRAF, KRAS, and NRAS. Lifirafenib participates in Phase II clinical trial in combination with PD-0325901 to treat the patients with solid tumor.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serine/threonine-protein kinase B-raf 21 Target ID: CHEMBL5145 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26208524	Inhibitor 8504	32.0 nM [IC50]
Serine/threonine-protein kinase A-Raf 3 Target ID: CHEMBL1169596 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26208524	Inhibitor 8504	5.6 nM [IC50]
Epidermal growth factor receptor 49 Target ID: CHEMBL2363049 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26208524	Inhibitor 8504	29.0 nM [IC50]

PubMed

Title	Date	PubMed
A high-performance liquid chromatography-tandem mass spectrometry method for the determination of lifrafenib, a novel RAF kinase and EGFR inhibitor, in human plasma and urine and its application in clinical pharmacokinetic study.	2019-03-20	30599278
Targeting oncogenic Raf protein-serine/threonine kinases in human cancers.	2018-09	30118796
BGB-283, a Novel RAF Kinase and EGFR Inhibitor, Displays Potent Antitumor Activity in BRAF-Mutated Colorectal Cancers.	2015-10	26208524

Sample Use Guides

In Vivo Use Guide

BGB-283 (lifirafenib) 5 or mg once a day

Route of Administration: Oral

Name

Type

Language

LIFIRAFENIB MALEATE

Official Name

English

LIFIRAFENIB SESQUIMALEATE

Preferred 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-, (2Z)-2-BUTENEDIOATE (2:3)

Systematic Name

English

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

Systematic Name

English

BGB-283 SESQUI-MALEATE

Code

English

LIFIRAFENIB MALEATE [USAN]

Common Name

English

Code System Code Type Description

NCI_THESAURUS

C174591