Androstanedione

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
CAS Number	846-46-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15994;
ChEMBL	ChEMBL1230438;
ChemSpider	193520;
DrugBank	DB01561;
PubChem CID	222865;
UNII	2KR72RNR8Z;
CompTox Dashboard (EPA)	DTXSID60880244 ;
	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/s1 Key: RAJWOBJTTGJROA-WZNAKSSCSA-N;
	SMILES C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]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 [77 °F], 100 kPa). Infobox references

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

^ ^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

Androstanedione (HMDB0000899) - Human Metabolome Database

[HMDB-1] "Human Metabolome Database: Showing metabocard for Androstanedione (HMDB0000899)".

[Becker2001-2] Kenneth L. Becker (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 994–. ISBN 978-0-7817-1750-2.

[OrwollBilezikian2009-3] 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.

[Kochakian2012-4] Charles D. Kochakian (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 171–. ISBN 978-3-642-66353-6.

[pmid16772150-5] 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.

[1]

[2]

[3]

[4]

[5]