Androstanedione
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| IUPAC name
(5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
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| Other names
Dihydroandrostenedione; 5α-Androstanedione; 5α-Androstane-3,17-dione
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C19H28O2 | |
| Molar mass | 288.431 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Androstanedione, also known as 5α-androstanedione or as 5α-androstane-3,17-dione, is a naturally occurring androstane (5α-androstane) steroid and an endogenous metabolite of androgens like testosterone, dihydrotestosterone (DHT), dehydroepiandrosterone (DHEA), and androstenedione.[1] It is the C5 epimer of etiocholanedione (5β-androstanedione).[1] Androstanedione is formed from androstenedione by 5α-reductase and from DHT by 17β-hydroxysteroid dehydrogenase.[2][3] It has some androgenic activity.[4]
In female genital skin, the conversion of androstenedione into DHT through 5α-androstanedione appears to be more important than the direct conversion of testosterone into DHT.[5]
References
[edit]- ^ a b "Human Metabolome Database: Showing metabocard for Androstanedione (HMDB0000899)".
- ^ Kenneth L. Becker (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 994–. ISBN 978-0-7817-1750-2.
- ^ Eric S. Orwoll; John P. Bilezikian; Dirk Vanderschueren (30 November 2009). Osteoporosis in Men: The Effects of Gender on Skeletal Health. Academic Press. pp. 296–. ISBN 978-0-08-092346-8.
- ^ Charles D. Kochakian (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 171–. ISBN 978-3-642-66353-6.
- ^ Stanczyk FZ (June 2006). "Diagnosis of hyperandrogenism: biochemical criteria". Best Pract Res Clin Endocrinol Metab. 20 (2): 177–91. doi:10.1016/j.beem.2006.03.007. PMID 16772150.
External links
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