Etiocholanolone

Etiocholanolone, also known as 5β-androsterone, as well as 3α-hydroxy-5β-androstan-17-one or etiocholan-3α-ol-17-one, is an etiocholane (5β-androstane) steroid as well as an endogenous 17-ketosteroid that is produced from the metabolism of testosterone. It causes fever, immunostimulation, and leukocytosis, and is used to evaluate adrenal cortex function, bone marrow performance, and in neoplastic disease to stimulate the immune system. Etiocholanolone is also known to be an inhibitory androstane neurosteroid,[1] acting as a positive allosteric modulator of the GABAA receptor,[2] and possesses anticonvulsant effects.[3] The unnatural enantiomer of etiocholanolone is more potent as a positive allosteric modulator of GABAA receptors and as an anticonvulsant than the natural form.[4]

Etiocholanolone
Skeletal formula of etiocholanolone
Ball-and-stick model of the etiocholanolone molecule
Clinical data
Other namesAetiocholanolone
5-Isoandrosterone
ATC code
  • none
Identifiers
  • (3R,5R,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
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H30O2
Molar mass290.447 g·mol−1
3D model (JSmol)
  • [H][C@]12CC[C@@]3([H])[C@]4([H])CCC(=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@H](O)C2
  • 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+/m1/s1 ☒N
  • Key:QGXBDMJGAMFCBF-BNSUEQOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Etiocholanolone has been studied as a pyrogenic steroid in the so-called steroid fever (or etiocholanolone fever),[5][6] a condiditon similar to familial mediterranean fever (FMF). Etiocholanolone (like pregnanolone) activates the pyrin inflammasome.[7] It is not known whether these endogenous steroids play a role in triggering FMF flares but they may make a link between stress, menstrual cycle and disease flares.[8][9]

Etiocholanolone is produced from 5β-dihydrotestosterone, with 3α,5β-androstanediol as an intermediate.

Chemistry
See also: List of neurosteroids

See also

References
  1. Reddy DS (2010). "Neurosteroids". Sex Differences in the Human Brain, their Underpinnings and Implications. pp. 113–37. doi:10.1016/B978-0-444-53630-3.00008-7. ISBN 9780444536303. PMC 3139029. PMID 21094889. {{cite book}}: |journal= ignored (help)
  2. 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.
  3. 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.
  4. 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.
  5. Heckel GP (April 1963). "Steroid fever". The Lancet. 281 (7285): 835–836. doi:10.1016/S0140-6736(63)91549-6.
  6. Kappas A, Palmer RH (July 1967). "Novel biological properties of steroid metabolites; fever-production in man". Journal of the Reticuloendothelial Society. 4 (4): 231–236. PMID 6056839.
  7. Magnotti F, Chirita D, Dalmon S, Martin A, Bronnec P, Sousa J, et al. (October 2022). "Steroid hormone catabolites activate the pyrin inflammasome through a non-canonical mechanism" (PDF). Cell Reports. 41 (2): 111472. doi:10.1101/2021.10.29.466454. PMC 9626387. PMID 36223753. S2CID 240345817.
  8. Karadag O, Tufan A, Yazisiz V, Ureten K, Yilmaz S, Cinar M, et al. (April 2013). "The factors considered as trigger for the attacks in patients with familial Mediterranean fever". Rheumatology International. 33 (4): 893–897. doi:10.1007/s00296-012-2453-x. PMID 22814791. S2CID 25599588.
  9. Akar S, Soyturk M, Onen F, Tunca M (May 2006). "The relations between attacks and menstrual periods and pregnancies of familial Mediterranean fever patients". Rheumatology International. 26 (7): 676–679. doi:10.1007/s00296-005-0041-z. PMID 16184383. S2CID 1617088.
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