Etiocholanedione

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Etiocholanedione
5beta-Androstanedione.svg
Names
IUPAC name
(5R,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
Etiocholane-3,17-dione; 5β-Androstanedione; 5β-Androstane-3,17-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
KEGG
UNII
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).
Infobox references

Etiocholanedione, also known as 5β-androstanedione or as etiocholane-3,17-dione, is a naturally occurring etiocholane (5β-androstane) steroid and an endogenous metabolite of androgens like testosterone, dihydrotestosterone, dehydroepiandrosterone (DHEA), and androstenedione.[1] It is the C5 epimer of androstanedione (5α-androstanedione).[1] Although devoid of androgenic activity like other 5β-reduced steroids, etiocholanedione has some biological activity of its own.[2][3] The compound has been found to possess potent haematopoietic effects in a variety of models.[2] In addition, it has been found to promote weight loss in animals and in a double-blind, placebo-controlled clinical study in humans conducted in 1993.[3][4] These effects are said to be similar to those of DHEA.[5] Unlike DHEA however, etiocholanedione cannot be metabolized further into steroid hormones like androgens and estrogens.[5]

References[edit]

  1. ^ a b "Human Metabolome Database: Showing metabocard for Etiocholanedione (HMDB0003769)". hmdb.ca. Retrieved 2018-07-13.
  2. ^ a b Bradlow HL, Murphy J, Byrne JJ (June 1999). "Immunological properties of dehydroepiandrosterone, its conjugates, and metabolites". Ann. N. Y. Acad. Sci. 876: 91–101. doi:10.1111/j.1749-6632.1999.tb07627.x. PMID 10415598.
  3. ^ a b Douglas McKeag; James L. Moeller (2007). ACSM's Primary Care Sports Medicine. Lippincott Williams & Wilkins. pp. 616–. ISBN 978-0-7817-7028-6.
  4. ^ James M. Rippe (15 March 2013). Lifestyle Medicine, Second Edition. CRC Press. pp. 559–. ISBN 978-1-4398-4544-8.
  5. ^ a b Clore JN (November 1995). "Dehydroepiandrosterone and body fat". Obes. Res. 3 Suppl 4: 613S–616S. doi:10.1002/j.1550-8528.1995.tb00234.x. PMID 8697065.

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