Etiocholanolone – Wikipedia

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Chemical compound

Etiocolanolone
Skeletal formula of etiocholanolone
Ball-and-stick model of the etiocholanolone molecule
Clinical data
Other names Aetiocholanolone
5-Isoandrosterone
ATC code
Identifiers

  • (3 R , 5 R ,8 R , 9 S ,ten 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

CAS Number
Pubchem CID
DrugBank
ChemSpider
SOME
Chebi
Clock
Chemical and physical data
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) 3-4-14-15-6-6-17 (21) 19 (15,2) 10-8-8- 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

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Etiocolanolone , 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, [first] acting as a positive allosteric modulator of the GABA A receptor, [2] and possesses anticonvulsant effects. [3] 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. [4]

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 [ edit ]

See also [ edit ]

References [ edit ]

  1. ^

    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 .

  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” . Mol. Pharmacol . 71 (6): 1582–90. 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” . Epilepsy . forty six (6): 819–27. 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): 3325–32. doi: 10.1007/s00213-014-3546-x . PMC  4134984 . PMID  24705905 .
  5. ^ Heckel, Georgeep. (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): 231–6. PMID  6056839 .
  7. ^ Magnotti, Flora; Chirita, Daria; Dalmon, Sarah; Martin, Amandine; BRONNEC, Pauline; Sousa, Jeremy; Helynck, Olivier; Lee, Wonyong; Kastner, Daniel; Chae, Jae Jin; McDermott, Michael F.; Belot, Alexandre; Popoff, Michel; Sève, Pascal; Georgin-Lavialle, Sophie; Munier-Lehmann, Hélène; Tran, you anh; Langhe, Ellen de; Wouters, Carine; Jamilloux, Yvan; Henry, Thomas (29 October 2021). “Steroid hormone catabolites Activate the pyrin inflammasome through a non-cannonical mechanism”. DOI: 10.101/2021.10.29.466454 . S2CID  240345817 . {{cite journal}} : Cite journal requires |journal= (help)
  8. ^ Karadag, Omer; Tufan, Abdurrahman; Without writing, parents; Urenen, Kemal; Yilmaz, Sedat; Cinar, Muhammet; Akdogan, Ali; Erdem, Hakan; Ozturk, Mehmet Akif; Pay, Salih; Dinc, Ayhan (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, Servet; Soyturk, Mujde; Onen, Fatos; Tunca, Mehmet (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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