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Biomedical subjects

M Hübner

Publications and source records attributed to M Hübner.

49 records · Page 3Linked to original sources
PubMed1983

The synthetic approach to STS 557 - structure activity relationships in 17 alpha-CH2X-substituted 19-nortestosterone derivatives.

The synthesis of 17 alpha-CH2X-substituted 19-nortestosterone derivatives (X = halogen, CN, N3, OH, NH2 etc.) is described. Starting with 1,4-dihydroestradiol 3-methyl ether the 17 alpha-CH2X-17 beta-hydroxy-moiety was introduced via a 17 beta-spiroepoxide which could be cleaved with various nucleophilic agents giving the desired derivatives. In the McPhail assay with immature rabbits some of these substances showed good progestagenic activity on oral administration. The influence of structural modifications on the activity is discussed. The best effect is observed if an additional double bond is introduced in position 9(10). While the 19-nortestosterone derivative with X = CN has only an activity of about 20% of that of norethisterone acetate, the introduction of a second double bond leads to a compound (STS 557) which has an oral potency more than ten times as high as levonorgestrel.

Animals↗
PubMed1982

Microbial transformation of 17 alpha-cyanomethyl-17-hydroxy-4,9-estradien-3-one (STS 557) and 17 alpha-cyanomethyl-19-nortestosterone by Mycobacterium smegmatis.

Microbial transformation of the new progestagen STS 557 (17 alpha-cyanomethyl-17-hydroxy-4,9-estradien-3-one) by Mycobacterium smegmatis yielded predominantly ring A-aromatized compounds: 17 alpha-cyanomethyl-1,3,5(10),9(11)-estratetraene-3, 17-diol, 17 alpha-cyanomethyl-1,3,5(10)-estratriene-3,17-diol and the corresponding 3-methyl ethers. The analogous compound without the 9(10) double bond, 17 alpha-cyanomethyl-19-nortestosterone, was transformed mainly to 5 alpha-hydrogenated metabolites: 17 alpha-cyanomethyl-17-hydroxy-5 alpha-estran-3-one, 17 alpha-cyanomethyl-17-hydroxy-5 alpha-1-estren-3-one, 17 alpha-cyanomethyl-5 alpha-estrane-3 alpha, 17-diol, and 17 alpha-cyanomethyl-5 alpha-estrane-3 beta, 17-diol. From these results, it is concluded that 4,9-dien-3-oxo compounds are not substrates for enzymatic 5 alpha-hydrogenation.

Biotransformation↗
PubMed1981

[Cholesterol- and weight reduction with a formula diet containing protein and legumes].

For weight reduction nine healthy subjects received a formula diet rich in protein and dietary fibers. The weight loss was 335 g/day. Cholesterol concentrations dropped about 30% in the course of 14 days. With a daily dose of 75 g protein-mixture the nitrogen-balance was slightly positive. Due to the high fiber content of the formula diet the stool weight was 78 +/- 45 g/day. No changes in blood chemistry and mineral content of urine were observed.

Body Weight↗
PubMed1980

[A new class of highly active progestagens: 17 alpha-CH2X-substituted gona-4,9(10)-dienes. 58. Steroids].

The synthesis of new gona-4,9(10)-dienes with a 17 alpha-CH2X-substituent (X = CN, N3, Cl or Br) is described. The progestagenic activity of these substances was studied in the McPhail assay using immature rabbits. The compound XVI (X = CN, STS 557) is the most potent one, showing an activity about ten times higher than D-norgestrel. Differences in the activity caused by different routes of application are discussed.

Animals↗
PubMed1979

[Partial effects of estrogens and 19-nortestoron derivatives].

In the present review the extragenital effects of steroidal estrogens and 19-norandrogen derivatives on mammalian organs and tissues are described. In detail experimental and clinical findings concerning the influence of these compounds on carbohydrate-, lipid- and protein metabolism, on the cardio-vascular system, the blood coagulation, the bone-tissue, the connective-tissue, the central nervous system and the immune system are summarised. These effects are mainly discussed as possible side effects and also as base for new therapeutic concepts.

Blood Coagulation↗