HOMEPRODUCTSCOMPANYCONTACTFAQResearchDictionaryPharmaSign Up FREE or Login

Sorafenib and its tosylate salt: a multikinase inhibitor for treating cancer.

Abstract
Sorafenib, a drug that targets malignant cancer cells and cuts off the blood supply feeding the tumour, has been crystallized as the free base, 4-(4-{3-[4-chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)-N-methylpyridine-2-carboxamide, C(21)H(16)ClF(3)N(4)O(3), (I), and as a tosylate salt, 4-(4-{3-[4-chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)-2-(N-methylcarbamoyl)pyridinium 4-methylbenzenesulfonate, C(21)H(17)ClF(3)N(4)O(3)(+)·C(7)H(7)O(3)S(-), (II). In both structures, the sorafenib molecule is in an extended conformation. The pyridine-2-carboxamide group exhibits a syn conformation of the N atoms in (I), whereas an almost anti orientation is present in (II). In both crystal structures, the two terminal groups, viz. pyridine-2-carboxamide and the trifluorophenyl ring, are oriented differently to the conformations found in enzyme-bound sorafenib. The sorafenib molecules in (I) are linked into zigzag chains by N-H···O hydrogen bonds, whereas in (II) the presence of the additional tosylate anion results in the formation of chains of fused hydrogen-bonded rings. This study reveals the variations in the solid-state conformation of the sorafenib molecule in different crystalline environments.
AuthorsK Ravikumar, B Sridhar, A K S Bhujanga Rao, M Pulla Reddy
JournalActa crystallographica. Section C, Crystal structure communications (Acta Crystallogr C) Vol. 67 Issue Pt 1 Pg. o29-32 (Jan 2011) ISSN: 1600-5759 [Electronic] United States
PMID21206080 (Publication Type: Journal Article)
Chemical References
  • Antineoplastic Agents
  • Benzenesulfonates
  • Enzyme Inhibitors
  • Phenylurea Compounds
  • Protein Kinase Inhibitors
  • Pyridines
  • Tosyl Compounds
  • Niacinamide
  • Sorafenib
Topics
  • Antineoplastic Agents (chemistry, therapeutic use)
  • Benzenesulfonates (chemistry, pharmacology, therapeutic use)
  • Crystallography, X-Ray
  • Enzyme Inhibitors (chemistry, pharmacology, therapeutic use)
  • Humans
  • Hydrogen Bonding
  • Molecular Conformation
  • Molecular Structure
  • Neoplasms (drug therapy)
  • Niacinamide (analogs & derivatives)
  • Phenylurea Compounds
  • Protein Kinase Inhibitors (chemistry, therapeutic use)
  • Pyridines (chemistry, pharmacology, therapeutic use)
  • Sorafenib
  • Tosyl Compounds (chemistry, pharmacology)

Join CureHunter, for free Research Interface BASIC access!

Take advantage of free CureHunter research engine access to explore the best drug and treatment options for any disease. Find out why thousands of doctors, pharma researchers and patient activists around the world use CureHunter every day.
Realize the full power of the drug-disease research graph!


Choose Username:
Email:
Password:
Verify Password:
Enter Code Shown: