Estimation of impurity profiles of drugs and related materials. Part 16: Identification of the side-products of the ethinylation step in the synthesis of contraceptive gestogens

P. Horváth, G. Balogh, J. Brlik, A. Csehi, F. Dravecz, Zs Halmos, A. Laukó, M. Rényei, K. Varga, S. Görög

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A new apolar impurity (3,17α-diethinyl-13-ethyl-3,5-gonadiene-17-ol, IIb) was detected and identified in norgestrel with the aid of thin-layer and high-performance chromatography and spectroscopic techniques. IIb is the product of the acid-catalysed dehydration of an overethinylated side product (Ib) of the ethinylation step in the synthesis of norgestrel. IIb can be determined by thin-layer densitometry and high-performance liquid chromatography. Another impurity (17α-ethinyl-13-ethyl-4-gonene-17-ol, IV), originating from a side product of the Birch reduction step in the synthesis of norgestrel was also detected and identified. The spot of IV overlaps with that of IIb in the TLC system of USP XXIII but can be separated and quantificated by more selective TLC systems and by gas chromatograpy.

Original languageEnglish
Pages (from-to)1343-1349
Number of pages7
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume15
Issue number9-10
DOIs
Publication statusPublished - Jun 1997

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Drug Contamination
Norgestrel
Contraceptive Agents
Impurities
Pharmaceutical Preparations
Betula
Densitometry
High performance liquid chromatography
Chromatography
Dehydration
Gases
High Pressure Liquid Chromatography
Acids

Keywords

  • 17α-Ethinyl-13-ethyl-4-gonen-17-ol
  • 3,17α-Diethinyl-13-ethyl-3,5-gonadiene-17-ol
  • Chromatography (TLC, GLC, HPLC)
  • Impurities in norgestrel
  • Impurity profiling
  • Norgestrel
  • Spectroscopy (UV, NMR, MS, GC/MS)

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmaceutical Science

Cite this

Estimation of impurity profiles of drugs and related materials. Part 16 : Identification of the side-products of the ethinylation step in the synthesis of contraceptive gestogens. / Horváth, P.; Balogh, G.; Brlik, J.; Csehi, A.; Dravecz, F.; Halmos, Zs; Laukó, A.; Rényei, M.; Varga, K.; Görög, S.

In: Journal of Pharmaceutical and Biomedical Analysis, Vol. 15, No. 9-10, 06.1997, p. 1343-1349.

Research output: Contribution to journalArticle

Horváth, P. ; Balogh, G. ; Brlik, J. ; Csehi, A. ; Dravecz, F. ; Halmos, Zs ; Laukó, A. ; Rényei, M. ; Varga, K. ; Görög, S. / Estimation of impurity profiles of drugs and related materials. Part 16 : Identification of the side-products of the ethinylation step in the synthesis of contraceptive gestogens. In: Journal of Pharmaceutical and Biomedical Analysis. 1997 ; Vol. 15, No. 9-10. pp. 1343-1349.
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