Volume 8 Issue 2
Apr.  2018
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Qun Xu, Ashraf Khan, Di Gao, Kristie M. Adams, Fatkhulla Tadjimukhamedov, Shane Tan, John T. Simpson. Structural confirmation of sulconazole sulfoxide as the primary degradation product of sulconazole nitrate[J]. Journal of Pharmaceutical Analysis, 2018, 8(2): 96-102.
Citation: Qun Xu, Ashraf Khan, Di Gao, Kristie M. Adams, Fatkhulla Tadjimukhamedov, Shane Tan, John T. Simpson. Structural confirmation of sulconazole sulfoxide as the primary degradation product of sulconazole nitrate[J]. Journal of Pharmaceutical Analysis, 2018, 8(2): 96-102.

Structural confirmation of sulconazole sulfoxide as the primary degradation product of sulconazole nitrate

  • Publish Date: Apr. 10, 2018
  • Sulconazole has been reported to degrade into sulconazole sulfoxide via sulfur oxidation; however, structural characterization data was lacking and the potential formation of an N-oxide or sulfone could not be excluded. To clarify the degradation pathways and incorporate the impurity profile of sulconazole into the United States Pharmacopeia–National Formulary (USP–NF) monographs, a multifaceted approach was utilized to confirm the identity of the degradant. The approach combines stress testing of sulco-nazole nitrate, chemical synthesis of the degradant via a hydrogen peroxide-mediated oxidation reaction, semi-preparative HPLC purification, and structural elucidation by LC―MS/MS and NMR spectroscopy. Structural determination was primarily based on the comparison of spectroscopic data of sulconazole and the oxidative degradant. The mass spectrometric data have revealed a McLafferty-type rearrange-ment as the characteristic fragmentation pathway for alkyl sulfoxides with aβ-hydrogen atom, and was used to distinguish the sulfoxide from N-oxide or sulfone derivatives. Moreover, the generated sulco-nazole sulfoxide was utilized as reference material for compendial procedure development and valida-tion, which provides support for USP monograph modernization.
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