Androstene-17-thioketals. 1st communication: glucocorticoid receptor binding, antiproliferative and antiinflammatory activities of some novel 20-thiasteroids (androstene-17-thioketals). Arzneimittel-Forschung. [Arzneimittelforschung] Journal article | | Title | Androstene-17-thioketals. 1st communication: glucocorticoid receptor binding, antiproliferative and antiinflammatory activities of some novel 20-thiasteroids (androstene-17-thioketals). | | Author(s) | Wojnar RJ, Varma RK, Free CA, Millonig RC, Karanewsky D, Lutsky BN | | Source | Arzneimittelforschung 1986 Dec; 36(12):1782-7. | | MeSH | Adrenalectomy
Androstenes
Animals
Anti-Inflammatory Agents
Cell Division
Croton Oil
DNA
Dose-Response Relationship, Drug
Edema
In Vitro
Liver
Mice
Rats
Receptors, Glucocorticoid
T-Lymphocytes
| | Abstract | The unique replacements of the alpha-hydroxyl and beta-ketol groups of corticoids at C17 with selected, simple alkylthio or (2-fluoroalkyl)thio groups resulted in the structurally novel steroids, C17-alkylthioketals of 9 alpha-fluoro-11 beta-hydroxy-androsta-1,4-diene-3,17-dione. The described androstene-17-thioketals (20-thiasteroids) had high affinities for the glucocorticoid receptor protein of rat liver cytosol. Most were more potent than triamcinolone acetonide, a clinically moderately potent corticoid, in antiproliferative and antiinflammatory activities in mice. Specifically, (11 beta, 17 alpha)-17-(ethylthio)-9 alpha-fluoro-11 beta-hydroxy-17-(methylthio) androsta-1,4-dien-3-one (tipredane, SQ 27,239) and (11 beta, 17 alpha)-17-(ethylthio)-9 alpha-fluoro-17-[2-(fluoroethyl)thio] - 11 beta - hydroxy-androsta-1,4-dien-3-one (SQ 28,300), topically applied, were as potent as halcinonide, a clinically highly potent corticoid, in inhibition of croton oil-induced edema in the mouse. It is suggested that both thiasteroids could be moderately to highly potent topical antiinflammatory agents in man. | | Language | eng | | Pub Type(s) | Journal Article
| | PubMed ID | 3494458 |
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