RETOSIBAN

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Search structure


Synonyms	GSK-221149 GSK-221149A GSK221149 GSK221149A Retosiban
Status
Molecule Category	UNKNOWN
UNII	GIE06H28OX
EPA CompTox	DTXSID00231559


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

Structure


InChI Key	PLVGDGRBPMVYPB-FDUHJNRSSA-N
Smiles	CC[C@H](C)[C@@H]1C(=O)N[C@H](C2Cc3ccccc3C2)C(=O)N1[C@@H](C(=O)N1CCOCC1)c1coc(C)n1
InChI	InChI=1S/C27H34N4O5/c1-4-16(2)23-25(32)29-22(20-13-18-7-5-6-8-19(18)14-20)26(33)31(23)24(21-15-36-17(3)28-21)27(34)30-9-11-35-12-10-30/h5-8,15-16,20,22-24H,4,9-14H2,1-3H3,(H,29,32)/t16-,22+,23+,24+/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C27H34N4O5
Molecular Weight	494.59
AlogP	2.04
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	6.0
Polar Surface Area	104.98
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	36.0

Bioactivity

Mechanism of Action	Action	Reference
Oxytocin receptor antagonist	ANTAGONIST	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	-	-	-	1-4	-

Assay Description	Organism	Bioactivity	Reference
Binding affinity to human oxytocin receptor	Homo sapiens	1.0 nM		Binding affinity to human oxytocin receptor	Homo sapiens	0.65 nM
Binding affinity to recombinant oxytocin receptor	None	4.1 nM
Binding affinity to human vasopressin V2 receptor	Homo sapiens	950.0 nM
Decrease in oxytocin-induced uterine contractions in iv dosed non-pregnant Sprague-Dawley rat	Rattus norvegicus	180.0 nM
Displacement of [3H]-oxytocin from oxytocin receptor in human uterus tissue	Homo sapiens	0.63 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL429736
DrugBank	DB11818
FDA SRS	GIE06H28OX
Guide to Pharmacology	8403
PDB	NU2
PubChem	11340891
SureChEMBL	SCHEMBL230301
ZINC	ZINC000006718496

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).