Etiocholanolone

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Etiocholanolone
Skeletal formula of etiocholanolone
Ball-and-stick model of the etiocholanolone molecule
Systematic (IUPAC) name
(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
Identifiers
CAS Number 53-42-9 YesY
ATC code none
PubChem CID: 5880
DrugBank DB02854 N
UNII 97CGB1M48I N
ChEBI CHEBI:28195 N
ChEMBL [https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL85799

<--Chemical data--> CHEMBL85799

<--Chemical data-->] N
Synonyms Aetiocholanolone
5-Isoandrosterone
Chemical data
Formula C19H30O2
Molecular mass 290.445 g/mol
  • [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
 NYesY (what is this?)  (verify)

Etiocholanolone, 3α-hydroxy-5β-androstan-17-one, is 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]

See also

References

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