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Current Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

Determination of Circular Dichroism and Ultraviolet Spectral Parameters of Norgestimate- and Other Delta4-3-Ketosteroid Oxime Isomers Via Normal Phase HPLC Method

Author(s): A. Szentesi, A. Gergely, P. Horvath, S. Maho, P. Matyus and Gy. Szasz

Volume 8, Issue 11, 2001

Page: [1341 - 1347] Pages: 7

DOI: 10.2174/0929867013372238

Price: $65

Abstract

The oxime formation reaction of therapeutical progestogen (levonorgestrel, levonorgestrel acetate, norethisterone), androgen (methyltestosterone, testosterone phenylpropionate) and anabolic (nortestosterone phenylpropionate) Delta 4-3-ketosteroids has been investigated. The ketosteroid-hydroxylamine reaction was monitored by reversed phase HPLC system. It was established, that under the experimental conditions applied the oxime formation was complete within 2 h. The reaction leads to the formation of Z and E oxime isomers. The isomers of norgestimate (levonorgestrel 17-acetate oxime) and other Delta 4-3-ketosteroid oximes have been separated by a new normal phase HPLC method. The identification (elution order assignation) and determination of the formation ratio of the isomers have been performed by 1H NMR spectroscopy on the basis of the chemical shift differences of 4-H signals. The on-line CD and UV spectra of the pure oxime isomers were recorded and then molar ellipticities and absorbances of the isomers were calculated in the wavelength range of 200-300 nm via parameter estimation method.

Keywords: circular dichroism, norgestimate, ketosteroid oxime, levonorgestrel, levonorgestrel acetate norethisterone, methylestosterone, testosterone phenylpropionate, ketsteroids


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