Compound: Allopregnanolone
SMILES: O=C([C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@H](C[C@H](O)CC4)CC3)C)CC2)CC1)C)C
InChIKey: AURFZBICLPNKBZ-SYBPFIFISA-N
Synonyms: Allopregnanolone, 516-54-1, Brexanolone, Allotetrahydroprogesterone, 3alpha-hydroxy-5alpha-pregnan-20-one, 3alpha,5alpha-THP, brexanolona, 3alpha-OH DHP, brexanolonum, 3alpha-Hydroxy-5alpha-dihydroprogesterone, (3alpha,5alpha)-3-hydroxypregnan-20-one, S39XZ5QV8Y, 1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone, CHEBI:50169, Pregnan-20-one, 3-hydroxy-, (3-alpha,5-alpha)-, 1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)ethanone, 3 alpha Hydroxy 5 alpha pregnan 20 one, 3 alpha-Hydroxy-5 alpha-pregnan-20-one, 3beta-Hydroxy-5alpha-tetrahydroprogesterone, alpha-Hydroxy-5 alpha-pregnan-20-one, 3, alpha-pregnan-20-one, 3 alpha-Hydroxy-5, Pregnan-20-one, 3-hydroxy-, (3beta,5alpha)-, RefChem:56411, Pregnanolone, (3alpha,5alpha)-, 208-224-2, 869-372-7, Allopregnan-3alpha-ol-20-one, SAGE-547, Zulresso, SGE-102, (3alpha)-Allopregnanolone, Brexanolone [USAN], 3a-Hydroxy-5a-pregnan-20-one, (3a)-Allopregnanolone, 3alpha,5alpha-tetrahydroprogesterone, 3a,5a-THP, CHEMBL207538, 1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one, 1-[(1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-7-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one, 3?-hydroxy-5?-pregnan-20-one, Allopregnan-3.alpha.-ol-20-one, tetrahydroprogesterone, 3-alpha,5-alpha-Pregnanolone, 3-alpha,5-alpha-Tetrahydroprogesterone, Allopregnan-3?-ol-20-one, Allopregnanolone(Brexanolone), 3a,5a-THPROG, UNII-S39XZ5QV8Y, Allopregnan-3a-ol-20-one, BRN 3211363, Allopregnalone, 3-alpha-Hydroxy-5-alpha-pregnan-20-one, Pregnan-20-one, 3-hydroxy-, (3a,5a)-, Allopregnanolone?, 3alpha-hydroxy-5alpha-pregnane-20-one, 5alpha-pregnane-3alpha-ol-20-one, Zulresso (TN), ALLO; Brexanolone; 3a,5a-tetrahydro Progesterone; 3a,5a-THP; (3a,5a)-3-hydroxy-pregnan-20-one, Y4B, 3a,5a-Pregnanolone, 5-alpha-Pregnan-20-one, 3-alpha-hydroxy-, BREXANOLONE [INN], 3-a-tetrahydroprogesterone, Brexanolone (USAN/INN), Pregnan-20-one, 3-hydroxy-, (3.alpha.,5.alpha.)-, Biomol-NT_000266, 3a,5a-Tetrahydroprogesterone, BIDD:PXR0069, 5a-Pregnan-3a-ol-20-one, BREXANOLONE [WHO-DD], SAGE547, 3-alpha-tetrahydroprogesterone, 3?-OH-DHP, 4-08-00-00664 (Beilstein Handbook Reference), 5a-Pregnane-3a-ol-20-one, orb422311, SCHEMBL588060, 5alpha-Pregnan-3a-ol-20-one, BPBio1_000728, GTPL4108, 3a-Hydroxy-5a-pregnane-20-one, Allopregnan-3I+/--ol-20-one, BREXANOLONE [ORANGE BOOK], 3a-Hydroxy-5a-dihydroprogesterone, 5|A-Pregnan-3|A-Ol-20-One, AURFZBICLPNKBZ-SYBPFIFISA-N, DEA NO. 2400, 5alpha pregnan 3alpha ol 20 one, DTXSID901016239, GLXC-07897, HMS3886D05, 1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-Hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, EX-A1195, (3a,5a)-3-Hydroxypregnan-20-one, BDBM50191342, HB0932, LMST02030156, MFCD00003677, MSK8589-100A, s5805, (+)-3a-Hydroxy-5a-pregnan-20-one, AKOS024285177, Pregnane-3alpha-ol-20-one, 5alpha-, CS-6401, DB11859, 3|A,5|A-THP;SAGE-547;Brexanolone, NCGC00163287-02, 5alpha-Pregnan-3alpha-ol-20-one, solid, AC-30353, AS-76408, DA-60419, FA158661, ST082264, HY-101107, NS00069758, Allopregnanolone; Allopregnan-3|A-Ol-20-One, ALLOPREGNAN-3.ALPHA.-OL-20-ONE [MI], D11149, EN300-19731899, BRD-K18172896-001-01-7, BRD-K18172896-001-02-5, Q28487680, (+)-3.ALPHA.-HYDROXY-5.ALPHA.-PREGNAN-20-ONE, 8E5D696A-EEBC-495D-A8C9-98FC9A593150, (3alpha)-Allopregnanolone Solution in Acetonitrile, 100ug/mL, 3beta-hydroxy-5beta,10alpha,14beta,17alpha-pregnan-20-one, 3beta-hydroxy-5beta,10alpha,14beta,17alpha-pregnan-20-one; Brexanolone, (1S,2S,7S,11S,14S,15S,5R,10R)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7. 0.0<2,7>.0<11,15>]heptadecane
Theoretical properties:
molecular_formula: C21H34O2
molecular_weight: 318.5 g/mol
exact_mass: 318.255880323 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 23
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 177 °C
Descriptions:
pubchem: Brexanolone is a 3-hydroxy-5alpha-pregnan-20-one in which the hydroxy group at position 3 has alpha-configuration. It is a metabolite of the sex hormone progesterone and used for the treatment of postpartum depression in women. It has a role as an antidepressant, a sedative, an intravenous anaesthetic, a GABA modulator and a human metabolite.
chebi: 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.
chembl: BREXANOLONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Allopregnanolone is a naturally occurring neurosteroid which is made in the body from the hormone progesterone. As a medication, allopregnanolone was referred to as brexanolone, sold under the brand name Zulresso, and was used to treat postpartum depression. It was given by injection into a vein.
Side effects of brexanolone may include sedation, sleepiness, dry mouth, hot flashes, and loss of consciousness. It was a neurosteroid and acts as a positive allosteric modulator of the GABAA receptor, the major biological target of the inhibitory neurotransmitter γ-aminobutyric acid (GABA).
Brexanolone was approved for medical use in the United States in 2019 and withdrawn from approval in 2025. The U.S. Food and Drug Administration (FDA) considers it to be a first-in-class medication. The long administration time, as well as the cost for a one-time treatment, have raised concerns about accessibility for many women.