Androsterone

Not to be confused with Androstenone, Androstenedione, or Androstadienol.

Androsterone
Skeletal formula of androsterone
Ball-and-stick model of the androsterone molecule
Clinical data
Other names3α-hydroxy-5α-androstan-17-one, 5α-androstan-3α-ol-17-one
ATC code
  • none
Identifiers
  • (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
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.159 Edit 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-HLUDHZFRSA-N checkY
  (verify)

Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone.[1] It is a weak androgen with a potency that is approximately 1/7 that of testosterone.[2] Androsterone is a metabolite of testosterone and dihydrotestosterone (DHT). In addition, it can be converted back into DHT via 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstanedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.[3][4]

Androsterone is also known to be an inhibitory androstane neurosteroid,[5][6] acting as a positive allosteric modulator of the GABAA receptor,[7] and possesses anticonvulsant effects.[8] The unnatural enantiomer of androsterone is more potent as a positive allosteric modulator of GABAA receptors and as an anticonvulsant than the natural form.[9] Androsterone's 3β-isomer is epiandrosterone, and its 5β-epimer is etiocholanolone. The 3β,5β-isomer is epietiocholanolone.

  1. ^ Motofei IG (November 2011). "A dual physiological character for cerebral mechanisms of sexuality and cognition: common somatic peripheral afferents". BJU International. 108 (10): 1634–1639. doi:10.1111/j.1464-410X.2011.10116.x. PMID 21489118. S2CID 25941894.
  2. ^ Scott T (1996). Concise Encyclopedia Biology. Walter de Gruyter. p. 49. ISBN 978-3-11-010661-9. Archived from the original on March 8, 2024. Retrieved May 25, 2012.
  3. ^ Stanczyk FZ, Bretsky (March 13, 2003). "Biosynthesis, Transport, and Metabolism of Steroid HormonesHenderson BE, Ponder BA, Ross RK". Hormones, Genes, and Cancer. Oxford University Press. p. 23. ISBN 978-0-19-513576-3. Retrieved May 25, 2012.
  4. ^ 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–E375. doi:10.1210/jc.2011-1997. PMID 22170725.
  5. ^ Reddy DS, Rogawski MA (2012). "Neurosteroids — Endogenous Regulators of Seizure Susceptibility and Role in the Treatment of Epilepsy". In Noebels JL, Avoli M, Rogawski MA, et al. (eds.). Jasper's Basic Mechanisms of the Epilepsies [Internet]. 4th edition. Bethesda (MD): National Center for Biotechnology Information (US). National Center for Biotechnology Information (US). PMID 22787590. Archived from the original on September 25, 2019. Retrieved August 29, 2017.
  6. ^ Reddy DS (2010). "Neurosteroids". Sex Differences in the Human Brain, their Underpinnings and Implications. Progress in Brain Research. Vol. 186. pp. 113–137. doi:10.1016/B978-0-444-53630-3.00008-7. ISBN 9780444536303. PMC 3139029. PMID 21094889.
  7. ^ 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". Molecular Pharmacology. 71 (6): 1582–1590. doi:10.1124/mol.106.033407. PMC 3788649. PMID 17341652. S2CID 44286086.
  8. ^ Kaminski RM, Marini H, Kim WJ, Rogawski MA (June 2005). "Anticonvulsant activity of androsterone and etiocholanolone". Epilepsia. 46 (6): 819–827. doi:10.1111/j.1528-1167.2005.00705.x. PMC 1181535. PMID 15946323.
  9. ^ Zolkowska D, Dhir A, Krishnan K, Covey DF, Rogawski MA (September 2014). "Anticonvulsant potencies of the enantiomers of the neurosteroids androsterone and etiocholanolone exceed those of the natural forms". Psychopharmacology. 231 (17): 3325–3332. doi:10.1007/s00213-014-3546-x. PMC 4134984. PMID 24705905.