Estimation of impurity profiles of drugs and related materials. 12. Isolation and identification of an isomeric impurity in danazol

G. Balogh, E. Csizer, G. Ferenczy, Z. Halmos, B. Herenyi, P. Horváth, A. Lauko, S. Gorog

Research output: Contribution to journalArticle

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 LV 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 UV 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
Volume12
Issue number2
Publication statusPublished - 1995

Fingerprint

Drug Contamination
Danazol
Isoxazoles
High performance liquid chromatography
High Pressure Liquid Chromatography
Impurities
Thin Layer Chromatography
Thin layer chromatography
Pharmaceutical Preparations
Densitometry
Reverse-Phase Chromatography
Gas Chromatography
Mass Spectrometry
Magnetic Resonance Spectroscopy
Gas chromatography
Nuclear magnetic resonance spectroscopy
Mass spectrometry
isodanazol

Keywords

  • danazol
  • HPLC
  • HPLC-UV
  • identification
  • impurity profiling
  • isodanazol
  • isolation
  • NMR spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)
  • Pharmaceutical Science
  • Pharmacology

Cite this

Estimation of impurity profiles of drugs and related materials. 12. Isolation and identification of an isomeric impurity in danazol. / Balogh, G.; Csizer, E.; Ferenczy, G.; Halmos, Z.; Herenyi, B.; Horváth, P.; Lauko, A.; Gorog, S.

In: Pharmaceutical Research, Vol. 12, No. 2, 1995, p. 295-298.

Research output: Contribution to journalArticle

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AU - Lauko, A.

AU - Gorog, S.

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