Details of the Drug

General Information of Drug (ID: DM3ZL2O)

Drug Name
GSK-557296
Synonyms Epelsiban; Epelsiban besylate; Premature ejaculation therapeutic (oral), GlaxoSmithKline
Indication
Disease Entry ICD 11 Status REF
Premature ejaculation HA03.0Z Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 518.6
Logarithm of the Partition Coefficient (xlogp) 3.5
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C30H38N4O4
IUPAC Name
(3R,6R)-6-[(2S)-butan-2-yl]-3-(2,3-dihydro-1H-inden-2-yl)-1-[(1R)-1-(2,6-dimethylpyridin-3-yl)-2-morpholin-4-yl-2-oxoethyl]piperazine-2,5-dione
Canonical SMILES
CC[C@H](C)[C@@H]1C(=O)N[C@@H](C(=O)N1[C@H](C2=C(N=C(C=C2)C)C)C(=O)N3CCOCC3)C4CC5=CC=CC=C5C4
InChI
InChI=1S/C30H38N4O4/c1-5-18(2)26-28(35)32-25(23-16-21-8-6-7-9-22(21)17-23)29(36)34(26)27(24-11-10-19(3)31-20(24)4)30(37)33-12-14-38-15-13-33/h6-11,18,23,25-27H,5,12-17H2,1-4H3,(H,32,35)/t18-,25+,26+,27+/m0/s1
InChIKey
UWHCWRQFNKUYCG-QUZACWSFSA-N
Cross-matching ID
PubChem CID
11634973
CAS Number
872599-83-2
UNII
T2EZ19HX73
DrugBank ID
DB11934
TTD ID
D09WYL

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Oxytocin receptor (OTR) TTSCIUP OXYR_HUMAN Antagonist [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT01021553) A Study To Evaluate the Safety, Tolerability, Pharmacokinetics and Pharmacodynamics of Two Oral Doses of GSK557296 in a Study in Men With Premature Ejaculation. U.S. National Institutes of Health.
2 Inhibition of ejaculation by the non-peptide oxytocin receptor antagonist GSK557296: a multi-level site of action. Br J Pharmacol. 2013 Aug;169(7):1477-85.