| Identification | Back Directory | [Name]
Sorafenib-d3 | [CAS]
1130115-44-4 | [Synonyms]
[2H3]-Sorafenib
Donafenib Tosylate
SORAFENIB D3 (BAY 43-9006 D3)
4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-(trideuteriomethyl)pyridine-2-carboxamide | [Molecular Formula]
C21H16ClF3N4O3 | [MDL Number]
MFCD08460931 | [MOL File]
1130115-44-4.mol | [Molecular Weight]
464.825 |
| Chemical Properties | Back Directory | [Melting point ]
202-204?C | [storage temp. ]
-20°C Freezer | [solubility ]
DMSO: soluble; Methanol: soluble | [form ]
A solid | [color ]
White to off-white | [InChI]
InChI=1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31) | [InChIKey]
MLDQJTXFUGDVEO-UHFFFAOYSA-N | [SMILES]
c1(Cl)ccc(NC(Nc2ccc(Oc3ccnc(C(=O)NC)c3)cc2)=O)cc1C(F)(F)F |
| Hazard Information | Back Directory | [Mechanism of action]
Donafenib blocks the proliferation of tumor cells by inhibiting Raf kinase and VEGFR tyrosine kinase. The deuterated methyl group in donafenib improves the metabolic stability of the drug, resulting in a prolonged half-life, reduced systemic clearance, and increased systemic exposure. Donafenib has shown significantly improved overall survival compared to sorafenib in the treatment of patients with unresectable HCC, while having a favorable safety and tolerability profile. | [Chemical Properties]
Off-White to Light Pink Solid | [Uses]
Labelled Sorafenib, a potent RAF kinase inhibitor. Antineoplastic. | [Synthesis]
The synthetic route began with the amidation of methyl formate 31.2 using chloromethane-d3-amine (31.1) as a deuterium source to afford CD3-amide 31.3 in high yield (98%). Aminophenol 31.4 was reacted with 31.2 in dimethyl sulfoxide via a SNAr displacement reaction to afford diaryl ether 31.5. Finally, aniline was reacted with isocyanate 31.6 to synthesize donafenib (31) from 31.3 in 79% yield.
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