Androsterone

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Androsterone
Androsterone.png
Systematic (IUPAC) name
(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
Clinical data
Legal status
?
Identifiers
CAS number53-41-8 YesY
ATC codeNone
PubChemCID 5879
ChemSpider5668 YesY
UNIIC24W7J5D5R YesY
ChEBICHEBI:16032 YesY
ChEMBLCHEMBL87285 YesY
Chemical data
FormulaC19H30O2 
Mol. mass290.440 g/mol
 YesY (what is this?)  (verify)
 
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Androsterone
Androsterone.png
Systematic (IUPAC) name
(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
Clinical data
Legal status
?
Identifiers
CAS number53-41-8 YesY
ATC codeNone
PubChemCID 5879
ChemSpider5668 YesY
UNIIC24W7J5D5R YesY
ChEBICHEBI:16032 YesY
ChEMBLCHEMBL87285 YesY
Chemical data
FormulaC19H30O2 
Mol. mass290.440 g/mol
 YesY (what is this?)  (verify)
Not to be confused with androstenone.

Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone and weak androgen with a potency that is approximately 1/7 that of testosterone.[1] In addition, it can be converted to dihydrotestosterone (DHT) from 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstenedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.[2][3] Androsterone is also known to be an inhibitory androstane neurosteroid,[4] acting as a positive allosteric modulator of the GABAA receptor,[5] and possesses anticonvulsant effects.[6]

Androsterone's 3β-isomer is epiandrosterone, and its 5β-epimer is etiocholanolone.

History[edit]

It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 liters (3,700 imp gal; 4,500 US gal) of male urine, from which they got 50 milligrams (0.77 gr) of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estrone.

Sources[edit]

Androsterone has been shown to naturally occur in pine pollen and is well known in many animal species.[7]

Effects[edit]

Androsterone is often advertised as influencing human behavior, but there is little data to substantiate its use as a pheromone.[citation needed]

Synthesis[edit]

Androsterone, its 3β-isomer, epiandrosterone, and its 5β-isomer, etiocholanolone, are produced in the body from 5α-reduced metabolites of dehydroepiandrosterone (DHEA), androstenediol, and androstenedione such as, in the case of androsterone, 5α-androstanediol via 17β-hydroxysteroid dehydrogenase and 5α-androstanedione via 3α-hydroxysteroid dehydrogenase.[citation needed]

See also[edit]

References[edit]

  1. ^ Thomas Scott (1996). Concise Encyclopedia Biology. Walter de Gruyter. p. 49. ISBN 978-3-11-010661-9. Retrieved 25 May 2012. 
  2. ^ Brian E. Henderson; Bruce A. J. Ponder; Ronald Keith Ross (13 March 2003). Hormones, Genes, and Cancer. Oxford University Press. p. 23. ISBN 978-0-19-513576-3. Retrieved 25 May 2012. 
  3. ^ Kamrath C, Hochberg Z, Hartmann MF, Remer T, Wudy SA (March 2012). "Increased activation of the alternative "backdoor" pathway in patients with 21-hydroxylase deficiency: evidence from urinary steroid hormone analysis". The Journal of Clinical Endocrinology and Metabolism 97 (3): E367–75. doi:10.1210/jc.2011-1997. PMID 22170725. 
  4. ^ Reddy DS (2010). "Neurosteroids: endogenous role in the human brain and therapeutic potentials". Prog. Brain Res. 186: 113–37. doi:10.1016/B978-0-444-53630-3.00008-7. PMC 3139029. PMID 21094889. 
  5. ^ Li P, Bracamontes J, Katona BW, Covey DF, Steinbach JH, Akk G (June 2007). "Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor". Mol. Pharmacol. 71 (6): 1582–90. doi:10.1124/mol.106.033407. PMID 17341652. 
  6. ^ Kaminski RM, Marini H, Kim WJ, Rogawski MA (June 2005). "Anticonvulsant activity of androsterone and etiocholanolone". Epilepsia 46 (6): 819–27. doi:10.1111/j.1528-1167.2005.00705.x. PMC 1181535. PMID 15946323. 
  7. ^ FOLIA HISTOCHEMICA ET CYTOBIOLOGICA Vol. 43, No. 2, 2005 pp. 71-79 Mammalian sex hormones in plants Anna Janeczko and Andrzej Skoczowski Institute of Plant Physiology, Polish Academy of Sciences, Kraków, Poland

External links[edit]