Sorafenib

Sorafenib
Clinical data
Trade names	Nexavar, others
Other names	Sorafenib tosylate
AHFS/Drugs.com	Monograph
MedlinePlus	a607051
License data	EU EMA: by INN; US DailyMed: Sorafenib; US FDA: Sorafenib;
Pregnancy; category	AU: D;
Routes of; administration	By mouth
ATC code	L01EX02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	38–49%
Protein binding	99.5%
Metabolism	Liver oxidation and glucuronidation (CYP3A4 & UGT1A9-mediated)
Elimination half-life	25–48 hours
Excretion	Feces (77%) and urine (19%)
Identifiers
	IUPAC name 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]; phenoxy]-N-methyl-pyridine-2-carboxamide;
CAS Number	284461-73-0;
PubChem CID	216239;
IUPHAR/BPS	5711;
DrugBank	DB00398;
ChemSpider	187440;
UNII	9ZOQ3TZI87;
KEGG	D08524; D06272;
ChEBI	CHEBI:50924;
ChEMBL	ChEMBL1336;
PDB ligand	BAX (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID7041128 ;
ECHA InfoCard	100.110.083
Chemical and physical data
Formula	C21H16ClF3N4O3
Molar mass	464.83 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNC(=O)c1cc(ccn1)Oc2ccc(cc2)NC(=O)Nc3ccc(c(c3)C(F)(F)F)Cl;
	InChI 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); Key:MLDQJTXFUGDVEO-UHFFFAOYSA-N;
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Sorafenib, sold under the brand name Nexavar, is a kinase inhibitor drug approved for the treatment of primary kidney cancer (advanced renal cell carcinoma), advanced primary liver cancer (hepatocellular carcinoma), FLT3-ITD positive AML and radioactive iodine resistant advanced thyroid carcinoma.