P06

Dabrafenib

Created: 2013-04-11
Last modified:  2021-03-13

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Chemical Details

Formal Charge0
Atom Count55
Chiral Atom Count0
Bond Count58
Aromatic Bond Count23
2D diagram of P06
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Chemical Component Summary

NameDabrafenib
SynonymsN-{3-[5-(2-aminopyrimidin-4-yl)-2-tert-butyl-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide
Systematic Name (OpenEye OEToolkits)N-[3-[5-(2-azanylpyrimidin-4-yl)-2-tert-butyl-1,3-thiazol-4-yl]-2-fluoranyl-phenyl]-2,6-bis(fluoranyl)benzenesulfonamide
FormulaC23 H20 F3 N5 O2 S2
Molecular Weight519.562
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01c4(N)nc(c1c(nc(s1)C(C)(C)C)c2c(c(ccc2)NS(=O)(=O)c3c(cccc3F)F)F)ccn4
SMILESCACTVS3.385CC(C)(C)c1sc(c2ccnc(N)n2)c(n1)c3cccc(N[S](=O)(=O)c4c(F)cccc4F)c3F
SMILESOpenEye OEToolkits1.7.6CC(C)(C)c1nc(c(s1)c2ccnc(n2)N)c3cccc(c3F)NS(=O)(=O)c4c(cccc4F)F
Canonical SMILESCACTVS3.385 CC(C)(C)c1sc(c2ccnc(N)n2)c(n1)c3cccc(N[S](=O)(=O)c4c(F)cccc4F)c3F
Canonical SMILESOpenEye OEToolkits1.7.6 CC(C)(C)c1nc(c(s1)c2ccnc(n2)N)c3cccc(c3F)NS(=O)(=O)c4c(cccc4F)F
InChIInChI1.03 InChI=1S/C23H20F3N5O2S2/c1-23(2,3)21-30-18(19(34-21)16-10-11-28-22(27)29-16)12-6-4-9-15(17(12)26)31-35(32,33)20-13(24)7-5-8-14(20)25/h4-11,31H,1-3H3,(H2,27,28,29)
InChIKeyInChI1.03 BFSMGDJOXZAERB-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB08912 
NameDabrafenib
Groups
  • approved
  • investigational
DescriptionDabrafenib mesylate (Tafinlar) is a reversible ATP-competitive kinase inhibitor and targets the MAPK pathway. It was approved on May 29, 2013, for the treatment of melanoma with V600E or V6000K mutation.[L41955] It was also used for metastatic non-small cell lung cancer with the same mutation.[L41955] In May 2018, Tafinlar (dabrafenib), in combination with Mekinist ([DB08911]), was approved to treat anaplastic thyroid cancer caused by an abnormal BRAF V600E gene.[L41955]
Synonyms
  • Dabrafenib
  • Dabrafenib mesylate
Brand NamesTafinlar
IndicationAs monotherapy, dabrafenib is indicated to treat unresectable or metastatic melanoma with BRAF V600E mutation as detected by an FDA-approved test.[L41955] In combination with [trametinib], dabrafenib is indicated to treat for: - the treatment of unresectable or metastatic melanoma with BRAF V600E or V600K mutations as detected by an FDA-approved test.[L41955] - the adjuvant treatment of melanoma with BRAF V600E or V600K mutations and involvement of lymph node(s), following complete resection.[L41955] - the treatment of metastatic non-small cell lung cancer (NSCLC) with BRAF V600E mutation.[L41955] - the treatment of locally advanced or metastatic anaplastic thyroid cancer (ATC) with BRAF V600E mutation and with no satisfactory locoregional treatment options.[L41955] - treatment of adult and pediatric patients six years and older with unresectable or metastatic solid tumours with BRAF V600E mutation who have progressed following prior treatment and have no satisfactory alternative treatment options. This indication is approved under accelerated approval based on the overall response rate and duration of response. Continued approval for this indication may be contingent upon verification and description of clinical benefit in a confirmatory trial(s).[L45548] - the treatment of pediatric patients one year of age and older with low-grade glioma (LGG) with a BRAF V600E mutation who require systemic therapy.[L45548] Dabrafenib has limitations of use: it is neither indicated for treating patients with colorectal cancer because of known intrinsic resistance to BRAF inhibition nor wild-type BRAF solid tumours.[L45548]
Categories
  • Amines
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • B-Raf serine-threonine kinase (BRAF) inhibitors
  • BCRP/ABCG2 Inhibitors
ATC-CodeL01EC02
CAS number1195765-45-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Serine/threonine-protein kinase B-rafMAALSGGGGGGAEPGQALFNGDMEPEAGAGAGAAASSAADPAIPEEVWNI...unknowninhibitor
RAF proto-oncogene serine/threonine-protein kinaseMEHIQGAWKTISNGFGFKDAVFDGSSCISPTIVQQFGYQRRASDDGKLTD...unknowninhibitor
Serine/threonine-protein kinase SIK1MVIMSEFSADPAGQGQGQQKPLRVGFYDIERTLGKGNFAVVKLARHRVTK...unknowninhibitor
Serine/threonine-protein kinase Nek11MLKFQEAAKCVSGSTAISTYPKTLIARRYVLQQKLGSGSFGTVYLVSDKK...unknowninhibitor
LIM domain kinase 1MRLTLLCCTWREERMGEEGSELPVCASCGQRIYDGQYLQALNADWHADCF...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 CHEMBL2028663
PubChem 44462760
ChEMBL CHEMBL2028663
ChEBI CHEBI:75045
CCDC/CSD ZOYYAQ, ZOYXUJ, ZOYXOD