Details of the Drug

General Information of Drug (ID: DM38CIV)

Drug Name

ELTANOLONE

Synonyms

Pregnanolone; 3alpha-Hydroxy-5beta-pregnan-20-one; 128-20-1; Pregnanolone II; Pregnan-3alpha-ol-20-one; Eltanolona; Eltanolonum; 5beta-Pregnan-3alpha-ol-20-one; Eltanolone [INN]; SKF 6455; NSC 82867; UNII-BXO86P3XXW; Eltanolonum [INN-Latin]; Eltanolona [INN-Spanish]; Allopregnan-3 beta-ol-20-one; (3alpha,5beta)-3-hydroxypregnan-20-one; 3alpha-Hydroxy-5beta-tetrahydroprogesterone; 3alpha,5beta-Epimeric pregnanolone; Pregnanolone, (3alpha,5beta)-isomer; BXO86P3XXW

Indication

Disease Entry	ICD 11	Status	REF
Premenstrual syndrome	GA34.40	Discontinued in Phase 3	[1]

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Clearance: The drug present in the plasma can be removed from the body at the rate of 22 mL/min/kg [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 4.7 hours [2]
Unbound Fraction: The unbound fraction of drug in plasma is 0.01% [2]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 2 L/kg [2]

Chemical Identifiers

Formula: C21H34O2
IUPAC Name: 1-[(3R,5R,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-/m1/s1
InChIKey: AURFZBICLPNKBZ-YZRLXODZSA-N

Cross-matching ID

PubChem CID: 31402
ChEBI ID: CHEMBL1712
CAS Number: 128-20-1
UNII: BXO86P3XXW
DrugBank ID: DB12308
TTD ID: D0B8YZ

Drug ADMET Endpoint Profile (DAE)^NEW

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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	[3]
GABA(A) receptor beta-2 (GABRB2)	TTZA1NY	GBRB2_HUMAN	Inhibitor	[3]
GABA(A) receptor gamma-2 (GABRG2)	TT06RH5	GBRG2_HUMAN	Inhibitor	[3]
Gamma-aminobutyric acid receptor (GAR)	TTNJYV2	NOUNIPROTAC	Inhibitor	[4]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aldo-keto reductase family 1 member C1 (AKR1C1)	OTQKR4CM	AK1C1_HUMAN	Biotransformations	[5]
Aldo-keto reductase family 1 member C2 (AKR1C2)	OTQ2XMO3	AK1C2_HUMAN	Biotransformations	[5]
Aldo-keto reductase family 1 member C3 (AKR1C3)	OTU2SXBA	AK1C3_HUMAN	Biotransformations	[6]
Aldo-keto reductase family 1 member C4 (AKR1C4)	OTW2MMOF	AK1C4_HUMAN	Regulation of Drug Effects	[7]

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800005875)
2	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	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.
4	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.
5	Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5.
6	Important roles of the AKR1C2 and SRD5A1 enzymes in progesterone metabolism in endometrial cancer model cell lines. Chem Biol Interact. 2015 Jun 5;234:297-308. doi: 10.1016/j.cbi.2014.11.012. Epub 2014 Nov 23.
7	Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone. Chem Biol Interact. 2003 Feb 1;143-144:503-13.