032

N-(3-{[5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]carbonyl}-2,4-difluorophenyl)propane-1-sulfonamide



Chemical Component Summary

NameN-(3-{[5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]carbonyl}-2,4-difluorophenyl)propane-1-sulfonamide
SynonymsVemurafenib; PLX4032
IdentifiersN-[3-[[5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]carbonyl]-2,4-difluoro-phenyl]propane-1-sulfonamide
FormulaC23 H18 Cl F2 N3 O3 S
Molecular Weight489.922
TypeNON-POLYMER
Isomeric SMILESCCCS(=O)(=O)Nc1ccc(c(c1F)C(=O)c2c[nH]c3c2cc(cn3)c4ccc(cc4)Cl)F
InChIInChI=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)
InChIKeyGPXBXXGIAQBQNI-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count51
Chiral Atom Count0
Bond Count54
Aromatic Bond Count23

Drug Info: DrugBank

DrugBank IDDB08881 
NameVemurafenib
Groups approved
DescriptionVemurafenib is a competitive kinase inhibitor with activity against BRAF kinase with mutations like V600E.[A31269] It exerts its function by binding to the ATP-binding domain of the mutant BRAF.[A31270] Vemurafenib was co-developed by Roche and Plexxikon and it obtained its FDA approval on August 17, 2011, under the company Hoffmann La Roche. After approval, Roche in collaboration with Genentech launched a broad development program. [L1012]
Synonyms
  • Vemurafenib
  • Vémurafénib
  • Vemurafenibum
Brand NamesZelboraf
IndicationVemurafenib is approved since 2011 for the treatment of metastatic melanoma with a mutation on BRAF in the valine located in the exon 15 at codon 600, this mutation is denominated as V600E.[A31270] The V600E mutation, a substitution of glutamic acid for valine, accounts for 54% of the cases of cutaneous melanoma.[A31271] Vemurafenib approval was extended in 2017, for its use as a treatment of adult patients with Erdheim-Chester Disease whose cancer cells present BRAF V600 mutation.[L1013] Erdheim-Chester disease is an extremely rare histiocyte cell disorder that affects large bones, large vessels, central nervous system, as well as, skin and lungs. It is reported an association of Erdheim-Chester disease and V600E mutation.[A31272]
Categories
  • Amides
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • B-Raf serine-threonine kinase (BRAF) inhibitors
  • BCRP/ABCG2 Inhibitors
ATC-Code
  • G01AE10
  • L01EC01
CAS number918504-65-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Serine/threonine-protein kinase B-rafMAALSGGGGGGAEPGQALFNGDMEPEAGAGAGAAASSAADPAIPEEVWNI...unknowninhibitor
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknowninhibitor
Cytochrome P450 2D6MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inducer
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1229517
PubChem 42611257
ChEMBL CHEMBL1229517
ChEBI CHEBI:63637
CCDC/CSD ODEROH06, ODEROH07, ODEROH08, ODEROH01, ODEROH09, ODEROH, ODEROH04, ODEROH02, ODEROH03, ODEROH05, ODEROH10