Misplaced Pages

Androstanedione

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
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-cyclopentaphenanthrene-3,17-dione
Other names Dihydroandrostenedione; 5α-Androstanedione; 5α-Androstane-3,17-dione
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: RAJWOBJTTGJROA-WZNAKSSCSA-N
SMILES
  • C12CCC(=O)C1CC32CC4(3CCC4=O)C
Properties
Chemical formula C19H28O2
Molar mass 288.431 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. It is the C5 epimer of etiocholanedione (5β-androstanedione). Androstanedione is formed from androstenedione by 5α-reductase and from DHT by 17β-hydroxysteroid dehydrogenase. It has some androgenic activity.

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.

References

  1. ^ "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.

External links

Endogenous steroids
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
Others
Androgen receptor modulators
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids


Stub icon

This article about a steroid is a stub. You can help Misplaced Pages by expanding it.

Stub icon

This biochemistry article is a stub. You can help Misplaced Pages by expanding it.

Categories: