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CHEBI:50169 - brexanolone

ChEBI IDCHEBI:50169
ChEBI Namebrexanolone
Stars
DefinitionA 3-hydroxy-5α-pregnan-20-one in which the hydroxy group at position 3 has α-configuration. It is a metabolite of the sex hormone progesterone and used for the treatment of postpartum depression in women.
Secondary ChEBI IDsCHEBI:32924, CHEBI:34347
Last Modified31 March 2019
SubmitterKirill Degtyarenko, Marcus Ennis
DownloadsMolfile
FormulaC21H34O2
Net Charge0
Average Mass318.501
Monoisotopic Mass318.25588
SMILES[H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])C(C)=O)[C@@]1(C)CC[C@@H](O)C2
InChIInChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1
InChIKeyAURFZBICLPNKBZ-SYBPFIFISA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Roles Classification
Biological Roles:
GABA modulator  A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Applications:
GABA modulator  A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
sedative  A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
ChEBI Ontology
Outgoing Relation(s)
brexanolone (CHEBI:50169) has role antidepressant (CHEBI:35469)
brexanolone (CHEBI:50169) has role GABA modulator (CHEBI:50268)
brexanolone (CHEBI:50169) has role human metabolite (CHEBI:77746)
brexanolone (CHEBI:50169) has role intravenous anaesthetic (CHEBI:38877)
brexanolone (CHEBI:50169) has role sedative (CHEBI:35717)
brexanolone (CHEBI:50169) is a 3-hydroxy-5α-pregnan-20-one (CHEBI:50170)
IUPAC Name 
3α-hydroxy-5α-pregnan-20-one
INNs  Source
brexanoloneWHO MedNet
brexanolonaWHO MedNet
brexanolonumWHO MedNet
brexanoloneWHO MedNet
Synonyms  Source
(3α,5α)-3-hydroxypregnan-20-oneNIST Chemistry WebBook
allopregnan-3α-ol-20-oneChemIDplus
3α-OH DHPKEGG COMPOUND
5α-pregnan-3α-ol-20-oneHMDB
3α,5α-THPChemIDplus
3α,5α-tetrahydroprogesteroneChemIDplus
Brand Name  Source
ZulressoChEBI
UniProt Name  Source
3α-hydroxy-5α-pregnan-20-oneUniProt
Manual XrefsDatabases
C13712KEGG COMPOUND
AllopregnanoloneWikipedia
HMDB0001449HMDB
LSM-19998LINCS
FDB022630FooDB
DB11859DrugBank
D11149KEGG DRUG
LMST02030130LIPID MAPS
Registry NumbersSources
Beilstein:3211363Beilstein
CAS:516-54-1ChemIDplus
CAS:516-54-1NIST Chemistry WebBook
CAS:516-54-1KEGG COMPOUND
Citations