Theme with variations. Identification of impurities in steroid 3-ketones

S. Görög, M. Babják, G. Balogh, J. Brlik, F. Dravecz, M. Gazdag, P. Horváth, A. Laukó, K. Varga

Research output: Contribution to journalArticle

Abstract

The 3-keto group occurs in a great variety of steroid hormone drugs: in all corticosteroids and in the majority of androgenic and gestogenic hormones as well as in their synthetic analogs. The formation of the 3-keto group and its environment in the synthetic derivatives takes place by means of complex synthetic or fermentation reaction steps. As a result of these and because of the reactivity of the keto group and its environment a large number of impurities related to the 3-keto group are formed in the course of the reaction steps and the degradation studies. In this paper the experiences from the authors' laboratory with the 3-ketone-related impurities in 19-nor-4-ene-3-ketosteroids (norgestrel, norethisterone, nandrolone, their esters, etc. and synthetic intermediates) as well as corticosteroids (prednisolone, mazipredone, etc.) are presented. The impurities include saturated 3-ketones (5α and β), 1-ene-3-ketones, 5(10)-ene-3-ketones, 3-deoxo and 3-ethinyl-3,5-diene derivatives, Δ6, Δ8(14), Δ6,18(14), 6-hydroxy (α and β), 10β-hydroxy and 6-keto derivatives in 4-ene-3-ketosteroids and Δ8, Δ9(11), 11α-hydroxy, 11-keto and 4-ene-3-keto derivatives in 1,4-diene-3-ketosteroids. The chromatographic, spectroscopic and hyphenated techniques used in this study include TLC, GC, HPLC with diode array UV detector, GC-MS, LC-MS and NMR methods.

Original languageEnglish
Number of pages1
JournalJournal de Pharmacie de Belgique
Volume53
Issue number3
Publication statusPublished - Dec 1 1998

ASJC Scopus subject areas

  • Medicine(all)

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    Görög, S., Babják, M., Balogh, G., Brlik, J., Dravecz, F., Gazdag, M., Horváth, P., Laukó, A., & Varga, K. (1998). Theme with variations. Identification of impurities in steroid 3-ketones. Journal de Pharmacie de Belgique, 53(3).