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Epiandrosterone

Chemical compound

Chemical compound

Epiandrosterone, or isoandrosterone, also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a steroid hormone with weak androgenic activity. It is a metabolite of testosterone and dihydrotestosterone (DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone (most likely mixed isomers), which was sufficient to find that the chemical formula was very similar to estrone.

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

Epiandrosterone is naturally produced by the enzyme 5α-reductase from the adrenal hormone DHEA. Epiandrosterone can also be produced from the natural steroids androstanediol via 17β-hydroxysteroid dehydrogenase or from androstanedione via 3β-hydroxysteroid dehydrogenase.

Applications

Epiandrosterone is used as a precursor to Desoxymethyltestosterone, Mestanolone, Vecuronium bromide & Pancuronium bromide, Zanoterone, & Estrone.

References

References

  1. (19 April 2016). "Handbook of Aqueous Solubility Data". CRC Press.
  2. (2006). "Natural Products". Krishna Prakashan Media.
  3. (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.
  4. (February 2000). "Influence of oral dehydroepiandrosterone (DHEA) on urinary steroid metabolites in males and females". Steroids.
  5. (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.
  6. (2001). "Steroid profiling in doping analysis". University Utrecht.
  7. (March 2004). "Pharmacokinetics of dehydroepiandrosterone and its metabolites after long-term daily oral administration to healthy young men". Fertility and Sterility.
  8. (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.
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5α-reduced-steroid-metabolites androgens androstanes
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