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
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.