Androstanedione

Not to be confused with androstanediol, androstenedione, androstenediol, or androstadienol.
Androstanedione
Names
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
Other names
Dihydroandrostenedione; 5α-Androstanedione; 5α-Androstane-3,17-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
UNII
  • InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1
    Key: RAJWOBJTTGJROA-WZNAKSSCSA-N
  • C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C
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).

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]

  1. ^ a b "Human Metabolome Database: Showing metabocard for Androstanedione (HMDB0000899)".
  2. ^ Kenneth L. Becker (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 994–. ISBN 978-0-7817-1750-2.
  3. ^ 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.
  4. ^ Charles D. Kochakian (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 171–. ISBN 978-3-642-66353-6.
  5. ^ 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.