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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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 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
Search PubMed titles vemurafenib
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

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MedChemExpress
Vemurafenib (links to external site)
Cat. No. HY-12057