EPELSIBAN

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Search structure


Synonyms	Epelsiban GSK-557296 GSK557296 GSK557296B Gsk557296
Status
Molecule Category	UNKNOWN
UNII	T2EZ19HX73


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	UWHCWRQFNKUYCG-QUZACWSFSA-N
Smiles	CC[C@H](C)[C@@H]1C(=O)N[C@H](C2Cc3ccccc3C2)C(=O)N1[C@@H](C(=O)N1CCOCC1)c1ccc(C)nc1C
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C30H38N4O4
Molecular Weight	518.66
AlogP	2.76
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	6.0
Polar Surface Area	91.84
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	38.0

Bioactivity

Mechanism of Action	Action	Reference
Oxytocin receptor antagonist	ANTAGONIST	PubMed PubMed


Protein: Oxytocin receptor Description: Oxytocin receptor Organism : Homo sapiens P30559 ENSG00000180914

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Vasopressin and oxytocin receptor	-	9	-	0	-

Assay Description	Organism	Bioactivity	Reference
Displacement of [3H]oxytocin from human oxytocin receptor	Homo sapiens	0.1259 nM
Reduction of oxytocin-induced uterine contraction in iv dosed rat uterine contractility model	Rattus norvegicus	192.0 nM
Antagonist activity at human OTR expressed in HEK293 cells assessed as decrease in calcium flux measured after 10 mins in presence of vasopressin by Fluo-4 dye based microplate reader based assay	Homo sapiens	9.2 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL2037511
DrugBank	DB11934
FDA SRS	T2EZ19HX73
PubChem	11634973
SureChEMBL	SCHEMBL1597672

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).