P06
Dabrafenib
| Created: | 2013-04-11 |
| Last modified: | 2021-03-13 |
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Chemical Details | |
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| Formal Charge | 0 |
| Atom Count | 55 |
| Chiral Atom Count | 0 |
| Bond Count | 58 |
| Aromatic Bond Count | 23 |
Chemical Component Summary | |
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| Name | Dabrafenib |
| Synonyms | N-{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 |
| Formula | C23 H20 F3 N5 O2 S2 |
| Molecular Weight | 519.562 |
| Type | NON-POLYMER |
Chemical Descriptors | |||
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| Type | Program | Version | Descriptor |
| SMILES | ACDLabs | 12.01 | c4(N)nc(c1c(nc(s1)C(C)(C)C)c2c(c(ccc2)NS(=O)(=O)c3c(cccc3F)F)F)ccn4 |
| SMILES | CACTVS | 3.385 | CC(C)(C)c1sc(c2ccnc(N)n2)c(n1)c3cccc(N[S](=O)(=O)c4c(F)cccc4F)c3F |
| SMILES | OpenEye OEToolkits | 1.7.6 | CC(C)(C)c1nc(c(s1)c2ccnc(n2)N)c3cccc(c3F)NS(=O)(=O)c4c(cccc4F)F |
| Canonical SMILES | CACTVS | 3.385 | CC(C)(C)c1sc(c2ccnc(N)n2)c(n1)c3cccc(N[S](=O)(=O)c4c(F)cccc4F)c3F |
| Canonical SMILES | OpenEye OEToolkits | 1.7.6 | CC(C)(C)c1nc(c(s1)c2ccnc(n2)N)c3cccc(c3F)NS(=O)(=O)c4c(cccc4F)F |
| InChI | InChI | 1.03 | 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) |
| InChIKey | InChI | 1.03 | BFSMGDJOXZAERB-UHFFFAOYSA-N |
Drug Info: DrugBank
| DrugBank ID | DB08912? |
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| Name | Dabrafenib |
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| Description | Dabrafenib 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 |
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| Brand Names |
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| Indication | As 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 |
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| ATC-Code | L01EC02 |
| CAS number | 1195765-45-7 |
Drug Targets
| Name | Target Sequence | Pharmacological Action | Actions |
|---|---|---|---|
| Serine/threonine-protein kinase B-raf | MAALSGGGGGGAEPGQALFNGDMEPEAGAGAGAAASSAADPAIPEEVWNI... | unknown | inhibitor |
| RAF proto-oncogene serine/threonine-protein kinase | MEHIQGAWKTISNGFGFKDAVFDGSSCISPTIVQQFGYQRRASDDGKLTD... | unknown | inhibitor |
| Serine/threonine-protein kinase SIK1 | MVIMSEFSADPAGQGQGQQKPLRVGFYDIERTLGKGNFAVVKLARHRVTK... | unknown | inhibitor |
| Serine/threonine-protein kinase Nek11 | MLKFQEAAKCVSGSTAISTYPKTLIARRYVLQQKLGSGSFGTVYLVSDKK... | unknown | inhibitor |
| LIM domain kinase 1 | MRLTLLCCTWREERMGEEGSELPVCASCGQRIYDGQYLQALNADWHADCF... | unknown | inhibitor |
| 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 Name | Reference |
|---|---|
| Pharos | CHEMBL2028663 |
| PubChem | 44462760 |
| ChEMBL | CHEMBL2028663 |
| ChEBI | CHEBI:75045 |
| CCDC/CSD | ZOYYAQ, ZOYXUJ, ZOYXOD |
