Etiocholanolone: Difference between revisions

{{Short description|Chemical compound}}

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| verifiedrevid = 413760240

| IUPAC_name = (3''R'',5''R'',8''R'',9''S'',10''S'',13''S'',14''S'')-3-Hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one

| image = Etiocholanolone.svg

| alt = Skeletal formula of etiocholanolone

| image2 = Etiocholanolone 3D ball.png

| alt2 = Ball-and-stick model of the etiocholanolone molecule

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 53-42-9

| ATC_prefix = none

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| ATC_supplemental =

| PubChem = 5880

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB02854

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 97CGB1M48I

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 28195

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 85799

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 5669

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| C=19 | H=30 | O=2

| synonyms = Aetiocholanolone<br />5-Isoandrosterone

| smiles = [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

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = QGXBDMJGAMFCBF-BNSUEQOYSA-N

'''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]], [[immunostimulant|immunostimulation]], and [[leukocytosis]], and is used to evaluate [[adrenal cortex]] function, [[bone marrow]] performance, and in [[neoplasm|neoplastic disease]] to stimulate the [[immune system]]. Etiocholanolone is also known to be an [[inhibitory postsynaptic potential|inhibitory]] [[androstane]] [[neurosteroid]],<ref name="pmid21094889">{{cite book | author = Reddy DS | title = Sex Differences in the Human Brain, their Underpinnings and Implications | chapter = Neurosteroids | journal = Prog. Brain Res. | volume = 186 | pages = 113–37 | year = 2010 | pmid = 21094889 | pmc = 3139029 | doi = 10.1016/B978-0-444-53630-3.00008-7 | series = Progress in Brain Research | isbn = 9780444536303 }}</ref> acting as a [[positive allosteric modulator]] of the [[GABAA receptor|GABA_A receptor]],<ref name="pmid17341652">{{cite journal | vauthors = Li P, Bracamontes J, Katona BW, Covey DF, Steinbach JH, Akk G | title = Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor | journal = Molecular Pharmacology | volume = 71 | issue = 6 | pages = 1582–1590 | date = June 2007 | pmid = 17341652 | pmc = 3788649 | doi = 10.1124/mol.106.033407 | s2cid = 44286086 }}</ref> and possesses [[anticonvulsant]] effects.<ref name="pmid15946323">{{cite journal | vauthors = Kaminski RM, Marini H, Kim WJ, Rogawski MA | title = Anticonvulsant activity of androsterone and etiocholanolone | journal = Epilepsia | volume = 46 | issue = 6 | pages = 819–827 | date = June 2005 | pmid = 15946323 | pmc = 1181535 | doi = 10.1111/j.1528-1167.2005.00705.x }}</ref> The unnatural enantiomer of etiocholanolone is more potent as a positive allosteric modulator of GABA_A receptors and as an anticonvulsant than the natural form.<ref>{{cite journal | vauthors = Zolkowska D, Dhir A, Krishnan K, Covey DF, Rogawski MA | title = Anticonvulsant potencies of the enantiomers of the neurosteroids androsterone and etiocholanolone exceed those of the natural forms | journal = Psychopharmacology | volume = 231 | issue = 17 | pages = 3325–3332 | date = September 2014 | pmid = 24705905 | pmc = 4134984 | doi = 10.1007/s00213-014-3546-x }}</ref>

Etiocholanolone has been studied as a [[pyrogenic]] steroid in the so-called steroid fever (or etiocholanolone fever),<ref>{{cite journal | vauthors = Heckel GP |title= Steroid fever |journal=The Lancet |date=April 1963 |volume=281 |issue=7285 |pages=835–836 |doi=10.1016/S0140-6736(63)91549-6}}</ref><ref>{{cite journal | vauthors = Kappas A, Palmer RH | title = Novel biological properties of steroid metabolites; fever-production in man | journal = Journal of the Reticuloendothelial Society | volume = 4 | issue = 4 | pages = 231–236 | date = July 1967 | pmid = 6056839 }}</ref> a condition similar to [[Familial Mediterranean fever|familial mediterranean fever]] (FMF). Etiocholanolone (like [[pregnanolone]]) activates the [[pyrin]] [[inflammasome]].<ref>{{cite journal | vauthors = Magnotti F, Chirita D, Dalmon S, Martin A, Bronnec P, Sousa J, Helynck O, Lee W, Kastner DL, Chae JJ, McDermott MF, Belot A, Popoff M, Sève P, Georgin-Lavialle S, Munier-Lehmann H, Tran TA, De Langhe E, Wouters C, Jamilloux Y, Henry T | display-authors = 6 | title = Steroid hormone catabolites activate the pyrin inflammasome through a non-canonical mechanism | journal = Cell Reports | volume = 41 | issue = 2 | pages = 111472 | date = October 2022 | pmid = 36223753 | doi = 10.1016/j.celrep.2022.111472|biorxiv=10.1101/2021.10.29.466454 | pmc = 9626387 | s2cid = 240345817 | doi-access=free }}</ref> It is not known whether these endogenous [[Steroid|steroids]] play a role in triggering [[Familial Mediterranean fever|FMF]] flares but they may make a link between [[Stress (biology)|stress]], [[menstrual cycle]] and disease flares.<ref>{{cite journal | vauthors = Karadag O, Tufan A, Yazisiz V, Ureten K, Yilmaz S, Cinar M, Akdogan A, Erdem H, Ozturk MA, Pay S, Dinc A | display-authors = 6 | title = The factors considered as trigger for the attacks in patients with familial Mediterranean fever | journal = Rheumatology International | volume = 33 | issue = 4 | pages = 893–897 | date = April 2013 | pmid = 22814791 | doi = 10.1007/s00296-012-2453-x | s2cid = 25599588 }}</ref><ref>{{cite journal | vauthors = Akar S, Soyturk M, Onen F, Tunca M | title = The relations between attacks and menstrual periods and pregnancies of familial Mediterranean fever patients | journal = Rheumatology International | volume = 26 | issue = 7 | pages = 676–679 | date = May 2006 | pmid = 16184383 | doi = 10.1007/s00296-005-0041-z | s2cid = 1617088 }}</ref>

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

==Chemistry==

{{See also|List of neurosteroids}}

== See also ==

* [[Androsterone]]

* [[Epiandrosterone]]

* [[Epietiocholanolone]]

* [[Etiocholanolone glucuronide]]

== References ==

{{Reflist}}

{{Steroid hormones}}

{{GABAAR PAMs}}

[[Category:Etiocholanes]]

[[Category:Neurosteroids]]

[[Category:GABAA receptor positive allosteric modulators]]

[[Category:Human metabolites]]

[[Category:World Anti-Doping Agency prohibited substances]]

{{steroid-stub}}