Basic information
- CAS
1195768-06-9- Standard SMILES
CC(C)(C)c1nc(-c2cccc(NS(=O)(=O)c3c(F)cccc3F)c2F)c(-c2ccnc(N)n2)s1.CS(=O)(=O)O- InChIKey
YKGMKSIHIVVYKY-UHFFFAOYSA-N- Molecular formula
- C24H24F3N5O5S3
- Average molar mass
- 615.7 g/mol
- Monoisotopic mass
- 615.08916653
Overview
Dabrafenib mesylate is a methanesulfonate (mesylate) salt prepared from equimolar amounts of dabrafenib and methanesulfonic acid. Used for treatment of metastatic melanoma. It has a role as an antineoplastic agent and a B-Raf inhibitor. It contains a dabrafenib.
Names & identifiers
- Preferred name
- Dabrafenib Mesylate
- IUPAC
- N-[3-[5-(2-aminopyrimidin-4-yl)-2-tert-butyl-1,3-thiazol-4-yl]-2-fluorophenyl]-2,6-difluorobenzenesulfonamide;methanesulfonic acid
- English name
- Dabrafenib Mesylate
- Molecular formula
- C24H24F3N5O5S3
- Molecular weight
- 615.66
Names & synonyms
Dabrafenib mesylate1195768-06-9TaflinarUNII-B6DC89I63EGSK 2118436BGSK-2118436BDabrafenib methanesulfonateGSK2118436BB6DC89I63Edabrafenib monomesylateGSK-2118436B MESYLATEGSK2118436 Methane sulfonate salt
Show more names
N-[3-[5-(2-Amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-4-thiazolyl]-2-fluorophenyl]-2,6-difluoro-benzenesulfonamide methanesulfonateDapafini mesylateabrafenibmesylateDabrfenib MesylateGSK2118436 MesylateGSK 2118436 MesylateGSK-2118436 MesylateDabrafenib Mesylate (API)
GSK2118436B, methane sulfonate saltGSK-2118436 METHANESULFONATE SALTGSK-2118436B METHANESULFONATE SALTCHEBI:75048DTXSID70152500Benzenesulfonamide, N-[3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-4-thiazolyl]-2-fluorophenyl]-2,6-difluoro-, methanesulfonate (1:1)BENZENESULFONAMIDE, N-(3-(5-(2-AMINO-4-PYRIMIDINYL)-2-(1,1-DIMETHYLETHYL)-4-THIAZOLYL)-2-FLUOROPHENYL)-2,6-DIFLUORO-, METHANESULFONATE (1:1)N-(3-(5-(2-aminopyrimidin-4-yl)-2-tert-butyl-1,3-thiazol-4-yl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide methanesulfonate
Properties
Computed structural properties
- Topological polar surface area
- 210 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 6
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 910
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 234 oC · >234oC (dec.)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly, Heated), Methanol (Slightly)
- form
- White solid.
- color
- White to Off-White
- Stability
- Hygroscopic
- InChIKey
- YKGMKSIHIVVYKY-UHFFFAOYSA-N
- SMILES
- S(O)(=O)(=O)C.FC1C(=CC=CC=1C1N=C(C(C)(C)C)SC=1C1C=CN=C(N)N=1)NS(C1C(=CC=CC=1F)F)(=O)=O
- NCI Dictionary of Cancer Terms
- dabrafenib mesylate
- FDA UNII
- 6 DC89I63E · B6DC89I63E
- NCI Drug Dictionary
- dabrafenib mesylate
- Symbol(GHS)
Safety & regulation
GHS classification
GHS Classification
Danger
H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P260, P264, P264+P265, P273, P280, P302+P352, P305+P354+P338, P317, P318, P319, P321, P332+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (66.7%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Dabrafenib mesylate
Ambiguous-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- hs_code
- 2935909099
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H319-H335-H302+H312+H332-H315
- Precautionary statements
- P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionDabrafenib Mesylate(1195768-06-9) is a salt form of Dabrafenib. Dabrafenib is an inhibitor of certain mutated forms of BRAF kinase, several of which may be associated with stimulating tumour growth (e.g. the BRAF V600E mutation), and Dabrafenib is also an inhibitor of BRAF V600-mutation positive cancer cell growth, both in vitro and in vivo.
DescriptionDabrafenib mesylate, sold by GlaxoSmithKline under the trade name Tafinlar, was approved by the U.S. FDA in May 2013 for the treatment of metastatic BRAF-mutant melanoma. Dabrafenib reversibly inhibits the BRAF(V600E) mutant kinase as a selective ATP-competitive inhibitor which results in tumor regression.
UsesDabrafenib is an inhibitor of mutated BRAF kinase and has clinical activity with a manageable safety profile in clinical trials of phase 1 and 2 in patients with BRAF(V600)-mutated metastatic melanoma.
Upstream & downstream products
Upstream raw materials
Related reactions
5 records
Compound notes
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