Details of the Drug

General Information of Drug (ID: DMNLHAC)

Drug Name

Allopregnanolone

Synonyms

516-54-1; Brexanolone; Allotetrahydroprogesterone; Allopregnan-3alpha-ol-20-one; 3alpha-hydroxy-5alpha-pregnan-20-one; SAGE-547; UNII-S39XZ5QV8Y; 3-alpha,5-alpha-Pregnanolone; 3alpha-OH DHP; 3alpha,5alpha-THP; 5alpha-Pregnan-3alpha-ol-20-one; 3a-Hydroxy-5a-pregnan-20-one; 3a,5a-THP; (3alpha)-Allopregnanolone; 3-alpha,5-alpha-Tetrahydroprogesterone; BRN 3211363; S39XZ5QV8Y; 3alpha-Hydroxy-5alpha-dihydroprogesterone; 3-alpha-Hydroxy-5-alpha-pregnan-20-one; CHEMBL207538; CHEBI:50169; SGE-102

Indication

Disease Entry	ICD 11	Status	REF
Depression	6A70-6A7Z	Approved	[1]
Postpartum depression	6E20.0	Approved	[1]
Status epilepticus seizure	8A66.1Y	Phase 3	[2]
Essential tremor or related tremors	8A04.1	Phase 2	[3]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

318.5

Logarithm of the Partition Coefficient (xlogp)

4.9

Rotatable Bond Count (rotbonds)

1

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

2

ADMET Property

Clearance: The total plasma clearance of drug is 1 L/h/kg []
Elimination: Following the administration of radiolabeled brexanolone, it was observed that 47% of the administrated dose was recovered largely as metabolites in the feces and 42% in urine, where less than 1% as recovered as unchanged brexanolone []
Half-life: The concentration or amount of drug in body reduced by one-half in 9 hours []
Metabolism: The drug is metabolized via the keto-reduction (via aldo-keto reductases), glucuronidation (via UDP-glucuronosyltransferases), and sulfation (via sulfotransferases) []
Vd: The volume of distribution (Vd) of drug is 3 L/kg []

Chemical Identifiers

Formula: C21H34O2
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
Canonical 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
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

Cross-matching ID

PubChem CID: 92786
ChEBI ID: CHEBI:50169
CAS Number: 516-54-1
DrugBank ID: DB11859
TTD ID: D00VZZ
INTEDE ID: DR0226
ACDINA ID: D00891

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
GABA(A) receptor alpha-1 (GABRA1)	TT1MPAY	GBRA1_HUMAN	Inhibitor	[4]
GABA(A) receptor beta-2 (GABRB2)	TTZA1NY	GBRB2_HUMAN	Inhibitor	[4]
GABA(A) receptor delta (GABRD)	TTGXH6N	GBRD_HUMAN	Inhibitor	[1]
GABA(A) receptor gamma-2 (GABRG2)	TT06RH5	GBRG2_HUMAN	Inhibitor	[4]
GABA(A) receptor gamma-3 (GABRG3)	TTEX6LM	GBRG3_HUMAN	Modulator	[5]
Gamma-aminobutyric acid receptor (GAR)	TTNJYV2	NOUNIPROTAC	Inhibitor	[6]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Aldo-keto reductase 1B1 (AKR1B1)_{Main DME}	DE7WS3H	ALDR_HUMAN	Substrate	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Allopregnanolone (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Oliceridine	DM6MDCF	Moderate	Additive CNS depression effects by the combination of Allopregnanolone and Oliceridine.	Acute pain [MG31]	[8]
Deutetrabenazine	DMUPFLI	Moderate	Additive CNS depression effects by the combination of Allopregnanolone and Deutetrabenazine.	Dystonic disorder [8A02]	[8]
Ingrezza	DMVPLNC	Moderate	Additive CNS depression effects by the combination of Allopregnanolone and Ingrezza.	Dystonic disorder [8A02]	[8]
Eslicarbazepine	DMZREFQ	Moderate	Additive CNS depression effects by the combination of Allopregnanolone and Eslicarbazepine.	Epilepsy/seizure [8A61-8A6Z]	[8]
Belladonna	DM2RBWK	Moderate	Additive CNS depression effects by the combination of Allopregnanolone and Belladonna.	Infectious gastroenteritis/colitis [1A40]	[8]
Remimazolam	DMLVSYX	Moderate	Additive CNS depression effects by the combination of Allopregnanolone and Remimazolam.	Labour/delivery anaesthesia complication [JB0C]	[8]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Hydrochloric acid	E00015	313	Acidulant
Citric acid monohydrate	E00271	22230	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Sodium citrate dihydrate	E00369	71474	Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Sodium hydroxide	E00234	14798	Alkalizing agent
Water	E00035	962	Solvent
Betadex sulfobutyl ether sodium	E00589	66577045	Solubilizing agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Brexanolone 100 mg/20 ml Injection	100 mg/20 ml	Injection	Intravenous

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References

1	Antibodies and venom peptides: new modalities for ion channels. Nat Rev Drug Discov. 2019 May;18(5):339-357.
2	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4	Neurosteroid analogues. 10. The effect of methyl group substitution at the C-6 and C-7 positions on the GABA modulatory and anesthetic actions of (... J Med Chem. 2005 Apr 21;48(8):3051-9.
5	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
6	Neurosteroid analogues. 11. Alternative ring system scaffolds: gamma-aminobutyric acid receptor modulation and anesthetic actions of benz[f]indenes. J Med Chem. 2006 Jul 27;49(15):4595-605.
7	FDA Label of Brexanolone. The 2020 official website of the U.S. Food and Drug Administration.
8	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.