vemurafenib   Click here for help

GtoPdb Ligand ID: 5893

Synonyms: PLX4032 | RG7204 | Zelboraf®
Approved drug PDB Ligand Immunopharmacology Ligand
vemurafenib is an approved drug (FDA (2011), EMA (2012))
Compound class: Synthetic organic
Comment: Vemurafenib is a Type-2 kinase inhibitor and was first approved by the FDA in 2011.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 100.3
Molecular weight 489.07
XLogP 6.39
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCCS(=O)(=O)Nc1ccc(c(c1F)C(=O)c1c[nH]c2c1cc(cn2)c1ccc(cc1)Cl)F
Isomeric SMILES CCCS(=O)(=O)Nc1ccc(c(c1F)C(=O)c1c[nH]c2c1cc(cn2)c1ccc(cc1)Cl)F
InChI InChI=1S/C23H18ClF2N3O3S/c1-2-9-33(31,32)29-19-8-7-18(25)20(21(19)26)22(30)17-12-28-23-16(17)10-14(11-27-23)13-3-5-15(24)6-4-13/h3-8,10-12,29H,2,9H2,1H3,(H,27,28)
InChI Key GPXBXXGIAQBQNI-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2011), EMA (2012))
Prodrug compound 2 [PMID: 26061392]
IUPAC Name Click here for help
N-(3-{[5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]carbonyl}-2,4-difluorophenyl)propane-1-sulfonamide
International Nonproprietary Names Click here for help
INN number INN
9286 vemurafenib
Synonyms Click here for help
PLX4032 | RG7204 | Zelboraf®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-6802253
Reactome Reaction Reactome logo R-HSA-6802938
Other databases
CAS Registry No. 918504-65-1 (source: SciFinder)
ChEBI CHEBI:63637
ChEMBL Ligand CHEMBL1229517
DrugBank Ligand DB08881
DrugCentral Ligand 4185
GtoPdb PubChem SID 178102516
PubChem CID 42611257
RCSB PDB Ligand 32, 032
Search Google for chemical match using the InChIKey GPXBXXGIAQBQNI-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GPXBXXGIAQBQNI
Search PubMed clinical trials vemurafenib
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Search PubMed titles/abstracts vemurafenib
SynPHARM 79553 (in complex with B-Raf proto-oncogene, serine/threonine kinase)
UniChem Compound Search for chemical match using the InChIKey GPXBXXGIAQBQNI-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GPXBXXGIAQBQNI-UHFFFAOYSA-N
Wikipedia Vemurafenib