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) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
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
CHEBI:1712
CAS Number
128-20-1
DrugBank ID
DB12308
TTD ID
D0B8YZ

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
3-oxo-5-alpha-steroid 4-dehydrogenase 1 (SRD5A1) OTQRET2B S5A1_HUMAN Biotransformations [5]
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Biotransformations [6]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Biotransformations [6]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Biotransformations [5]
Aldo-keto reductase family 1 member C4 (AKR1C4) OTW2MMOF AK1C4_HUMAN Regulation of Drug Effects [7]
Interleukin-1 beta (IL1B) OT0DWXXB IL1B_HUMAN Protein Interaction/Cellular Processes [8]
Steroid 17-alpha-hydroxylase/17,20 lyase (CYP17A1) OTZKVLVJ CP17A_HUMAN Biotransformations [9]
Molecular Interaction Atlas (MIA) 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 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.
6 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.
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.
8 Central opioid inhibition of neuroendocrine stress responses in pregnancy in the rat is induced by the neurosteroid allopregnanolone. J Neurosci. 2009 May 20;29(20):6449-60. doi: 10.1523/JNEUROSCI.0708-09.2009.
9 5alpha-reduced C21 steroids are substrates for human cytochrome P450c17. Arch Biochem Biophys. 2003 Oct 15;418(2):151-60. doi: 10.1016/j.abb.2003.07.003.