Structure via PubChem · Public domain (PubChem)
allopregnanolone
Sign in to saveAlso known as brexanolone
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.
Key facts
- Drug.image
- Allopregnanolone.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 225
- Drug.alt
- Skeletal formula of allopregnanolone
- Drug.image2
- Allopregnanolone-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 225
- Drug.alt2
- Ball-and-stick model of the allopregnanolone molecule
- Drug.USAN
- brexanolone
- Drug.tradename
- Zulresso
- Drug.MedlinePlus
- a619037
- Drug.DailyMedID
- Brexanolone
- Drug.licence_US
- Zulresso
- Drug.routes_of_administration
- Intravenous
- Drug.class
- Neurosteroids; Antidepressants
- Drug.ATC_prefix
- N06
- Drug.ATC_suffix
- AX29
- Drug.legal_US
- Schedule IV
via Wikipedia infobox
Chemical data
- Formula
- C21H34O2
- Molecular weight
- 318.5 g/mol
- IUPAC name
- 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
- SMILES
- CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)C)C
- InChIKey
- AURFZBICLPNKBZ-SYBPFIFISA-N
- XLogP
- 4.9
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 318.255880328
Show 7 more facts
- chemical formula
- C₂₁H₃₄O₂
- isomeric SMILES
- CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)C)C
- found in taxon
- Homo sapiens
- canonical SMILES
- O=C(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C
- Commons category
- Allopregnanolone
- stereoisomer of
- pregnanolone
- legal status (medicine)
- boxed warning
Sources (8)
via Wikidata · CC0
~16 min read
Encyclopedic overview
23 sectionsContents
- Medical uses
- Clinical efficacy
- Side effects
- Biological function
- Mechanism of action
- Molecular interactions
- Biphasic actions at the GABA<sub>A</sub> receptor
- Antidepressant effects
- Pharmacology
- Pharmacokinetics
- Chemistry
- Biosynthesis
- Derivatives
- History
- Society and culture
- Names
- Legal status
- Available forms
- Research
- See also
- References
- Further reading
- External links
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).
Excerpted from Wikipedia’s “allopregnanolone” article, available under the CC BY-SA 4.0 licence.