Preparation of 3-ketodesogestrel metabolites by microbial transformation and chemical synthesis

Steroids

Volumn 62, Issue 5, 1997, Pages 437-443

  Groh, Helmut ^a   Schön, Renate ^b   Ritzau, Michael ^b   Kasch, Helmut ^b   Undisz, Katrin ^b   Hobe, Gerhard ^b  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b HANS KNÖLL INSTITUTE   (Germany)

Author keywords

3 Ketodesogestrel; Chemical synthesis; Metabolite; Microbial transformation; NMR

Indexed keywords

DESOGESTREL; ETONOGESTREL; GESTAGEN; LEVONORGESTREL; SODIUM BOROHYDRIDE;

ARTICLE; BACTERIUM TRANSFORMATION; CLOSTRIDIUM; DRUG STRUCTURE; DRUG SYNTHESIS; MYCOBACTERIUM SMEGMATIS; NONHUMAN; RHODOCOCCUS;

CLOSTRIDIUM; DESOGESTREL; MYCOBACTERIUM; PROGESTERONE CONGENERS; RHODOCOCCUS;

BACTERIA (MICROORGANISMS); CLOSTRIDIUM; CLOSTRIDIUM PARAPUTRIFICUM; MYCOBACTERIUM SMEGMATIS; RHODOCOCCUS; RHODOCOCCUS RHODOCHROUS;

EID: 0030985876     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(97)00014-7     Document Type: Article

References (22)

1. Gerhards E, Hecker W, Hitze H, Nieuweboer B, Bellmann B (1971), Zum Stoffwechsel von Norethisteron (17α-Äthinyl-4-östren-17β-ol-3-on) und DL-sowie D-Norgestrel (18-Methyl-17α-äthinyl-4-östren-17β-ol-3-on) beim Menschen. Acta Endocr Copenh 68:219-248.
2. Viinikka L (1979). Metabolism of a new synthetic progestagen, Org 2969, by human liver in vitro. J Steroid Biochem 10:353-357.
3. Madden S, Back DJ, Orme M L'E (1990). Metabolism of the contraceptive steroid desogestrel by human liver in vitro. J Steroid Biochem 35:281-288.
4. Wild MJ, Rudland PS, Back DJ (1993). Metabolism of the oral contraceptive steroids ethynylestradiol, norgestimate and 3-ketodesogestrel by a human cancer cell line (HEC-1A) and endometrial tissue in vitro. J Steroid Biochem 45:407-420.
5. Kaufmann G, Schumann G, Hörhold C (1986). Influence of 1-double bond and 11β-hydroxy group on stereospecific microbial reductions of 4-en-3-oxo-steroids. J Steroid Biochem 25:561-566.
6. Schubert K, Schumann G, Kaufmann G (1983). Influence of a 9-double bond on stereospecific microbial 4,5-reductions. J Steroid Biochem 18:75-80.
7. Schubert K, Schlegel J, Hörhold C, Frischleder H (1970). Metaboliten von 4-Chlor-17α-methyl-17β-hydroxy-1,4-androstadien-3-on durch mikrobielle Hydrierung. J Steroid Biochem 1:229-236.
8. Hobe G, Schön R, Hörhold C, Hübner M, Schade W, Schubert K (1982). Microbial transformation of 17α-cyanomethyl-17-hydroxy-4,9-estradien-3-one (STS 557) and 17α-cyanomethyl-19-nortestosterone by Mycobacterium smegmatis. Steroids 39:399-410.
9. Schubert K, Schlegel J, Böhme KH, Hörhold C (1967). Mikrobielle Hydrierungs-und Dehydrierungs-Reaktionen bei Δ4-3-Ketosteroiden mit einer 6-Hydroxy-gruppe. Biochim Biophys Acta 144:132-138.
10. Höbe G, Dänhardt S, Busch W (1979). Umwandlung von 19-Norgestagenen in Östrogene durch Mikroorganismen des Rinderpansens. Arch exper Vet med 33:495-498.
11. Groh H, Komel R, Deppmeyer V, Schade W, Hörhold C (1980). Steroid transforming enzymes from microorganisms: The reverse reaction of the steroid 1-dehydrogenase from Nocardia. J Steroid Biochem 13:1413-1415.
12. Corey EJ, Suggs JW (1975). Pyridinium chlorochromate, an efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Lett 31:2647-2650.
13. Wiebe JP, Deline C, Buckingham KD (1985). Synthesis of the allylic gonadal steroids, 3α-hydroxy-4-pregnen-20-one and 3α-hydroxy-4-androsten-17-one, and of 3α-hydroxy-5α-pregnan-20-one. Steroids 45:39-51.
14. Junghans K (1976). Selektive elektrochemische Reduktionen von Δ8-Estratetraen-Derivaten in flüssigem Ammoniak: Stereoselektivität der Birch-Reduktion in Gegenwart von Anilin. Chem Ber 109:395-402.
15. Hübner M, Füssel I, Ponsold K (1984). Synthese potentieller Metaboliten der STS 557 (Dienogest). Teil I: Metaboliten mit einem hydrierten A/B-Ringsystem. Pharmazie 39:462-463.
16. Rao PN, Cessa JW, Kim HK (1994). Preparative chemical methods for aromatization of 19-nor-Δ4-3-oxo steroids. Steroids 59:621-627.
17. Velluz L, Legrand M (1961). Zirkulardichroismus und Raumstruktur. Neue Ergebnisse im Steroidgebiet. Angew Chem 73:601-611.
18. Bridgeman JE, Cherry PC, Clegg AS, Evans JM, Jones ERH, Kasal A, Kumar V, Meakins GD, Morisawa Y, Richards EE, Woodgate PD (1970). Microbiological hydroxylation of steroids. Part I. Proton magnetic resonance spectra of ketones, alcohols, and acetates in the androstane, pregnane, and estrane series. J Chem Soc (C): 250-257.
19. Hörhold C, Atrat P, Deppmeyer V, Garbert A, Flemming CH, Schubert K (1976). Reinigung einer 3-Oxo-steroid:[2,6-Dichlorphenolindophenol]-Al-oxidoreductase aus Nocardia opaca mit Hilfe der Affinitätschromatographie. Zeitschr Allg Mikrobiol 16: 559-561.
20. Höbe G, Schön R, Wehrberger K, Ritter P, Schade W, Hillesheim HG (1989). Studies on the biotransformation of the progestagen Dienogest in the rabbit. Exper Clin Endocrinol 94:203-210.
21. Raynaud JP, Cousty C, Salmon J (1974). Metabolic studies of R 2453, a highly potent progestin. J Steroid Biochem 5:324.
22. Kaufmann G, Schumann G, Wollweber L, Hüller L, Atrat, P (1990). Steroid-dehydrogenases in nocardioform bacteria studied by electrophoresis and immuno blotting techniques. J Basic Microbiol 30:415-423.