Estimation of Impurity Profiles of Drugs and Related Materials. 12. Isolation and Identification of an Isomeric Impurity in Danazol

Gábor Balogh, Éva Csizér, György G. Ferenczy, Zsuzsanna Halmos, Bulcsu Herényi, Péter Horváth, Anna Laukó, Sándor Görög

Research output: Article

16 Citations (Scopus)

Abstract

We report on a new isomeric impurity of danazol. This impurity designated as isodanazol was detected by reversed-phase high-performance liquid chromatography (HPLC) and thin-layer chromatography (TLC). Its structure was determined after separation by preparative HPLC. Mass spectrometry revealed the isomeric nature of the impurity while the UV spectrum indicated profound difference in the isoxazole moieties. The structure of the isomeric isoxazole ring in isodanazol was determined by NMR spectroscopy using COSY, HETCOR and NOE measurements. The difference between the U V spectra of danazol and isodanazol is explained on the basis of the difference between the aromaticities of their isoxazole rings supported by quantum chemical calculations. The quantitative determination of the impurity down to the 0.05% level can be performed by HPLC, gas chromatography and TLC densitometry.

Original languageEnglish
Pages (from-to)295-298
Number of pages4
JournalPharmaceutical Research: An Official Journal of the American Association of Pharmaceutical Scientists
Volume12
Issue number2
DOIs
Publication statusPublished - febr. 1995

ASJC Scopus subject areas

  • Biotechnology
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry
  • Pharmacology (medical)

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