CHEBI:50169 - brexanolone

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ChEBI Name brexanolone
ChEBI ID CHEBI:50169
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:34347, CHEBI:32924
Supplier Information ChemicalBook:CB5418550, eMolecules:531093, ZINC000004081043
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Formula C21H34O2
Net Charge 0
Average Mass 318.49346
Monoisotopic Mass 318.25588
InChI InChI=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
InChIKey AURFZBICLPNKBZ-SYBPFIFISA-N
SMILES [H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@]([H])(C(C)=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@H](O)C2
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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.
Application(s): antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
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.
intravenous anaesthetic

sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
brexanolona WHO MedNet
brexanolone WHO MedNet
brexanolone WHO MedNet
brexanolonum WHO MedNet
Synonyms Sources
(3α,5α)-3-hydroxypregnan-20-one NIST Chemistry WebBook
3α,5α-tetrahydroprogesterone ChemIDplus
3α,5α-THP ChemIDplus
3α-hydroxy-5α-dihydroprogesterone ChemIDplus
3α-hydroxy-5α-pregnan-20-one UniProt
3α-OH DHP KEGG COMPOUND
5α-pregnan-3α-ol-20-one HMDB
allopregnan-3α-ol-20-one ChemIDplus
allopregnanolone KEGG COMPOUND
allotetrahydroprogesterone ChemIDplus
SAGE-547 ChemIDplus
SGE-102 ChemIDplus
Brand Name Source
Zulresso ChEBI
Manual Xrefs Databases
Allopregnanolone Wikipedia
C13712 KEGG COMPOUND
D11149 KEGG DRUG
DB11859 DrugBank
FDB022630 FooDB
HMDB0001449 HMDB
LMST02030130 LIPID MAPS
LSM-19998 LINCS
View more database links
Registry Numbers Types Sources
3211363 Beilstein Registry Number ChemIDplus
516-54-1 CAS Registry Number NIST Chemistry WebBook
516-54-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10625505 PubMed citation Europe PMC
11739473 PubMed citation Europe PMC
19290593 PubMed citation Europe PMC
28370307 PubMed citation Europe PMC
28619476 PubMed citation Europe PMC
28666923 PubMed citation Europe PMC
28779545 PubMed citation Europe PMC
29453777 PubMed citation Europe PMC
29636114 PubMed citation Europe PMC
30177236 PubMed citation Europe PMC
30362283 PubMed citation Europe PMC
30481569 PubMed citation Europe PMC
30701996 PubMed citation Europe PMC
9501247 PubMed citation Europe PMC
Last Modified
31 March 2019
General Comment
2019-03-31 The name 'allopregnanolone' is commonly used in the literature when this compound is discussed as an endogenous neurosteroid. The name 'brexanolone' is used in the literature when the compound is discussed in the context of its use as a medication. Zulresso is the brand name of the medication.