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

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...

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Bibliographic Details
Published in:Journal of pharmaceutical and biomedical analysis 1997-06, Vol.15 (9), p.1343-1349
Main Authors: Horváth, P., Balogh, G., Brlik, J., Csehi, A., Dravecz, F., Halmos, Zs, Laukó, A., Rényei, M., Varga, K., Görög, S.
Format: Article
Language:English
Subjects:
17α-Ethinyl-13-ethyl-4-gonen-17-ol
3,17α-Diethinyl-13-ethyl-3,5-gonadiene-17-ol
Analysis
Biological and medical sciences
Chromatography (TLC, GLC, HPLC)
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Contraceptives, Oral, Synthetic - chemical synthesis
Contraceptives, Oral, Synthetic - isolation & purification
General pharmacology
Impurities in norgestrel
Impurity profiling
Medical sciences
Norgestrel
Norgestrel - analogs & derivatives
Norgestrel - chemical synthesis
Norgestrel - isolation & purification
Pharmacology. Drug treatments
Progesterone Congeners - chemical synthesis
Progesterone Congeners - isolation & purification
Spectroscopy (UV, NMR, MS, GC/MS)
Spectrum Analysis
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Summary: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.
ISSN:0731-7085
1873-264X
DOI:10.1016/S0731-7085(96)02008-0