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Epiandrosterone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Epiandrosterone
Skeletal formula of epiandrosterone
Ball-and-stick model of the epiandrosterone molecule
Clinical data
ATC code
  • none
Identifiers
  • (3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.006.877Edit this at Wikidata
Chemical and physical data
FormulaC19H30O2
Molar mass290.447 g·mol−1
3D model (JSmol)
  • O=C2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4C[C@@H](O)CC[C@]34C)C
  • InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18-,19-/m0/s1 checkY
  • Key:QGXBDMJGAMFCBF-LUJOEAJASA-N checkY
  (verify)

Epiandrosterone, orisoandrosterone,[1][2] also known as3β-androsterone,3β-hydroxy-5α-androstan-17-one, or5α-androstan-3β-ol-17-one, is asteroid hormone with weakandrogenic activity. It is ametabolite oftestosterone anddihydrotestosterone (DHT). It was first isolated in 1931, byAdolf Friedrich Johann Butenandt andKurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystallineandrosterone (most likely mixed isomers), which was sufficient to find that the chemical formula was very similar toestrone.

Epiandrosterone has been shown to naturally occur in most mammals including pigs.[3]

Epiandrosterone is naturally produced by the enzyme 5α-reductase from the adrenal hormoneDHEA.[4][5][6][7][verification needed] Epiandrosterone can also be produced from the natural steroidsandrostanediol via17β-hydroxysteroid dehydrogenase or fromandrostanedione via3β-hydroxysteroid dehydrogenase.[8]

See also

[edit]

References

[edit]
  1. ^Yalkowsky SH, He Y, Jain P (19 April 2016).Handbook of Aqueous Solubility Data (Second ed.). CRC Press. pp. 1209–.ISBN 978-1-4398-0246-5.
  2. ^Agarwal OP (2006).Natural Products. Krishna Prakashan Media. pp. 298–.ISBN 978-81-87224-85-3.
  3. ^Raeside JI, Renaud RL, Marshall DE (March 1992). "Identification of 5 alpha-androstane-3 beta,17 beta-diol and 3 beta-hydroxy-5 alpha-androstan-17-one sulfates as quantitatively significant secretory products of porcine Leydig cells and their presence in testicular venous blood".The Journal of Steroid Biochemistry and Molecular Biology.42 (1):113–20.doi:10.1016/0960-0760(92)90017-d.PMID 1558816.S2CID 53274020.
  4. ^Callies F, Arlt W, Siekmann L, Hübler D, Bidlingmaier F, Allolio B (February 2000). "Influence of oral dehydroepiandrosterone (DHEA) on urinary steroid metabolites in males and females".Steroids.65 (2):98–102.doi:10.1016/s0039-128x(99)00090-2.PMID 10639021.S2CID 2630118.
  5. ^Labrie F, Cusan L, Gomez JL, Martel C, Bérubé R, Bélanger P, et al. (May 2008). "Changes in serum DHEA and eleven of its metabolites during 12-month percutaneous administration of DHEA".The Journal of Steroid Biochemistry and Molecular Biology.110 (1–2):1–9.doi:10.1016/j.jsbmb.2008.02.003.PMID 18359622.S2CID 24975983.
  6. ^van de Kerkhof DH (2001).Steroid profiling in doping analysis (Ph.D. thesis). University Utrecht.hdl:1874/328.
  7. ^Acacio BD, Stanczyk FZ, Mullin P, Saadat P, Jafarian N, Sokol RZ (March 2004)."Pharmacokinetics of dehydroepiandrosterone and its metabolites after long-term daily oral administration to healthy young men".Fertility and Sterility.81 (3):595–604.doi:10.1016/j.fertnstert.2003.07.035.PMID 15037408.
  8. ^Huang XF, Luu-The V (August 2001). "Gene structure, chromosomal localization and analysis of 3-ketosteroid reductase activity of the human 3(alpha-->beta)-hydroxysteroid epimerase".Biochimica et Biophysica Acta.1520 (2):124–30.doi:10.1016/s0167-4781(01)00247-0.PMID 11513953.

Further reading

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