Etiocholanolone Other names Aetiocholanolone 5-Isoandrosterone ATC code
(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 Formula C 19 H 30 O 2 Molar mass 290.447 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
N Y (what is this?)
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 is produced from 5β-dihydrotestosterone , with 3α,5β-androstanediol as an intermediate .
Chemistry [ ]
See also [ ]
Androsterone
Epiandrosterone
Epietiocholanolone
Etiocholanolone glucuronide
References [ ]
^ Reddy DS (2010). Neurosteroids: endogenous role in the human brain and therapeutic potentials . Prog. Brain Res . Progress in Brain Research. Vol. 186. pp. 113–37. doi :10.1016/B978-0-444-53630-3.00008-7 . ISBN 9780444536303 . PMC 3139029 . PMID 21094889 .
^ 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 . PMC 3788649 . PMID 17341652 . S2CID 44286086 .
^ 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 .
^ 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): 3325–32. doi :10.1007/s00213-014-3546-x . PMC 4134984 . PMID 24705905 .
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