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Details

Stereochemistry ACHIRAL
Molecular Formula C21H16ClF3N4O3
Molecular Weight 464.825
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SORAFENIB

SMILES

CNC(=O)C1=NC=CC(OC2=CC=C(NC(=O)NC3=CC(=C(Cl)C=C3)C(F)(F)F)C=C2)=C1

InChI

InChIKey=MLDQJTXFUGDVEO-UHFFFAOYSA-N
InChI=1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)

HIDE SMILES / InChI

Description

Sorafenib (BAY 43-9006), marketed as Nexavar by Bayer, is a drug approved for the treatment of advanced renal cell carcinoma (primary kidney cancer, hepatocellular carcinoma and for the treatment of patients with locally recurrent or metastatic, progressive, differentiated thyroid carcinoma (DTC) that is refractory to radioactive iodine treatment. It has also received "Fast Track" designation by the FDA for the treatment of advanced hepatocellular carcinoma (primary liver cancer), and has since performed well in Phase III trials. Sorafenib was shown to interact with multiple intracellular (CRAF, BRAF and mutant BRAF) and cell surface kinases (KIT, FLT- 3, VEGFR- 2, VEGFR- 3, and PDGFR- ß). Several of these kinases are thought to be involved in angiogenesis. Thus, sorafenib may inhibit tumor growth by a dual mechanism, acting either directly on the tumor (through inhibition of Raf and Kit signaling) and/or on tumor angiogenesis (through inhibition of VEGFR and PDGFR signaling). Sorafenib inhibited tumor growth of the murine renal cell carcinoma, RENCA, and several other human tumor xenografts in athymic mice. A reduction in tumor angiogenesis was seen in some tumor xenograft models.

CNS Activity

Approval Year

TargetsConditions
PubMed

PubMed

TitleDatePubMed
Gateways to clinical trials.
2005 Mar
Patents

Sample Use Guides

In Vivo Use Guide
The recommended daily dose of NEXAVAR (tosylate salt of sorafenib) is 400 mg (2 x 200 mg tablets) taken twice daily, without food (at least 1 hour before or 2 hours after eating). Treatment should continue until the patient is no longer clinically benefiting from therapy or until unacceptable toxicity occurs. 432 433 434 435 436 437 438 439 Management of suspected adverse drug reactions may require temporary interruption and/or dose reduction of NEXAVAR therapy. When dose reduction is necessary, the NEXAVAR dose may be reduced to 400 mg once daily. If additional dose reduction is required, NEXAVAR may be reduced to a single 400 mg dose every other day
Route of Administration: Oral
In Vitro Use Guide
Patient-derived glioblastoma cells with low concentrations of sorafenib caused a dramatic dose dependent inhibition of proliferation (IC(50), 1.5 microM) and induction of apoptosis and autophagy. Sorafenib inhibited phosphorylation of signal transducer and activator of transcription 3 (Stat3) and expression of cyclins, D and E. In contrast, AKT was not modulated by sorafenib
Name Type Language
SORAFENIB
EMA EPAR   INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
SORAFENIB [USAN]
Common Name English
SORAFENIB [MART.]
Common Name English
SORAFENIB [EMA EPAR]
Common Name English
SORAFENIB [WHO-DD]
Common Name English
2-PYRIDINECARBOXAMIDE, 4-(4-((((4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL)AMINO)CARBONYL)AMINO)PHENOXY)-N-METHYL-
Systematic Name English
BAY 43-9006
Code English
SORAFENIB [MI]
Common Name English
4-(4-(3-(4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL)UREIDO)PHENOXY)-N(SUP 2)-METHYLPYRIDINE-2-CARBOXAMIDE
Systematic Name English
SORAFENIB [VANDF]
Common Name English
BAY-43-9006
Code English
SORAFENIB [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QL01XE05
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
WHO-ATC L01XE05
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
NDF-RT N0000175076
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
EMA ASSESSMENT REPORTS NEXAVAR (AUTHORIZED: CARCINOMA, HEPATOCELLULAR, CARINOMA, RENAL CELL)
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
LIVERTOX 894
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
NDF-RT N0000175605
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
Code System Code Type Description
LactMed
284461-73-0
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
INN
8234
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
RXCUI
495881
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY RxNorm
NCI_THESAURUS
C61948
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
MESH
C471405
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
PUBCHEM
216239
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY SWITZERF
EPA CompTox
284461-73-0
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
WIKIPEDIA
SORAFENIB
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
ChEMBL
CHEMBL1336
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
HSDB
284461-73-0
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
IUPHAR
5711
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
DRUG BANK
DB00398
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
MERCK INDEX
M10116
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY Merck Index
CAS
284461-73-0
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY
EVMPD
SUB23139
Created by admin on Tue Mar 06 11:17:00 UTC 2018 , Edited by admin on Tue Mar 06 11:17:00 UTC 2018
PRIMARY