vemurafenib (CED0002246)

Record Information
Version1.0
Creation Date2016-06-03 13:33:51 UTC
Update Date2026-08-21 23:35:24 UTC
Accession NumberCHEM045661
Identification
Common Namevemurafenib
ClassSmall Molecule
Description
Vemurafenib is an organic compound with the formula C23H18ClF2N3O3S and an average molecular weight of 489.92 g/mol. vemurafenib belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. This compound acts as an inhibitor of the serine/threonine-protein kinase B-raf (BRAF). It is found in or released from three recorded sources, including electrical and electronic equipment such as electric hearing aids, as well as pharmaceuticals and veterinary products, specifically antineoplastic agents and gynecologicals. The recorded route of exposure for this substance is oral.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
VemurafenibumChEBI
ZelborafChEBI
Chemical FormulaC23H18ClF2N3O3S
Average Molecular Mass489.922 g/mol
Monoisotopic Mass489.073 g/mol
CAS Registry Number1029872-54-5
IUPAC NameN-{3-[5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluorophenyl}propane-1-sulfonamide
Traditional Namevemurafenib
SMILESCCCS(=O)(=O)NC1=C(F)C(C(=O)C2=CNC3=NC=C(C=C23)C2=CC=C(Cl)C=C2)=C(F)C=C1
InChI IdentifierInChI=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 KeyGPXBXXGIAQBQNI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-phenylketones
Alternative Parents
Substituents
  • Aryl-phenylketone
  • 3-phenylpyridine
  • Sulfanilide
  • Pyrrolopyridine
  • Benzoyl
  • Halobenzene
  • Fluorobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Pyridine
  • Aryl fluoride
  • Organosulfonic acid amide
  • Organic sulfonic acid amide
  • Substituted pyrrole
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Vinylogous halide
  • Aminosulfonyl compound
  • Pyrrole
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00036 g/LALOGPS
logP4.95ALOGPS
logP4.62ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)7.17ChemAxon
pKa (Strongest Basic)3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.92 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity121.97 m³·mol⁻¹ChemAxon
Polarizability48.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-054o-9212300000-fbdbb92088febd3eda6bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0024900000-4911e6c7ad52fd2c2896Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-0281900000-e08321c7aa665a4f4c73Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-6494400000-4ea2fc0a4cbd6d24d3ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1190000000-fd8302ac94aec0904dc4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0020900000-de3f93933bd01bde416fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002k-0142900000-fa7a706c558c555f7315Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-4980500000-02de2d40bd79e37e37f1Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2330.0Log mg/kg[1300:4100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
Pathways
1 pathway
Vemurafenib Drug Metabolism Action Pathway
Vemurafenib Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Serine/threonine-protein kinase B-raf structureClick to view 3D structureSerine/threonine-protein kinase B-rafP15056HumansPredicted (SEA)0.0778492
RAF proto-oncogene serine/threonine-protein kinase structureClick to view 3D structureRAF proto-oncogene serine/threonine-protein kinaseP04049HumansPredicted (SEA)0.0778492
Click to view 3D structureDual specificity mitogen-activated protein kinase kinase 4P47809Mus musculusPredicted (SEA)0.0778492
Serine/threonine-protein kinase A-Raf structureClick to view 3D structureSerine/threonine-protein kinase A-RafP10398HumansPredicted (SEA)0.0778492
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)6.30579
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)2.17978
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)1.24559
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)1.63483
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)0.856341
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)14.5578
Click to view 3D structureMitogen-activated protein kinase kinase kinase kinase 5Q9Y4K4HumansPredicted (SEA)4.7488
Mitogen-activated protein kinase kinase kinase 20 structureClick to view 3D structureMitogen-activated protein kinase kinase kinase 20Q9NYL2HumansPredicted (SEA)3.81461
Protein-tyrosine kinase 6 structureClick to view 3D structureProtein-tyrosine kinase 6Q13882HumansPredicted (SEA)6.61718
Macrophage colony-stimulating factor 1 receptor structureClick to view 3D structureMacrophage colony-stimulating factor 1 receptorP07333HumansPredicted (SEA)10.0426
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)37.5233
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)6.53933
Serine/threonine-protein kinase Nek2 structureClick to view 3D structureSerine/threonine-protein kinase Nek2P51955HumansPredicted (SEA)8.25202
Proto-oncogene tyrosine-protein kinase receptor Ret structureClick to view 3D structureProto-oncogene tyrosine-protein kinase receptor RetP07949HumansPredicted (SEA)13.0787
Receptor-interacting serine/threonine-protein kinase 2 structureClick to view 3D structureReceptor-interacting serine/threonine-protein kinase 2O43353HumansPredicted (SEA)4.35956
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)44.1405
Activated CDC42 kinase 1 structureClick to view 3D structureActivated CDC42 kinase 1Q07912HumansPredicted (SEA)6.61718
Dual specificity mitogen-activated protein kinase kinase 5 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 5Q13163HumansPredicted (SEA)3.58106
TGF-beta receptor type-2 structureClick to view 3D structureTGF-beta receptor type-2P37173HumansPredicted (SEA)4.20386
Click to view 3D structureSerine/threonine-protein kinase Nek11Q8NG66HumansPredicted (SEA)0.856341
Tyrosine-protein kinase Tec structureClick to view 3D structureTyrosine-protein kinase TecP42680HumansPredicted (SEA)17.3604
Concentrations
Not Available
External Links
DrugBank IDDB08881
HMDB IDHMDB0259779
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkVemurafenib
Chemspider ID24747352
ChEBI ID63637
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21609436
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21639808
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22028422
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22037033
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22083257
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22180495