retosiban

Also known as GSK-221,149-A

Retosiban also known as GSK-221,149-A is an oral drug which acts as an oxytocin receptor antagonist. It is being developed by GlaxoSmithKline for the treatment of preterm labour. Retosiban has high affinity for the oxytocin receptor (Ki = 0.65 nM) and has greater than 1400-fold selectivity over the related vasopressin receptors

Chemical data

Formula: C16H18N2O
Molecular weight: 254.33 g/mol
IUPAC name: 2-[(1R)-5,8-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-yl]-1H-pyridin-4-one
SMILES: CC1=C2CCN[C@H](C2=C(C=C1)C)C3=CC(=O)C=CN3
InChIKey: RDMQELOVSPETKY-INIZCTEOSA-N
XLogP: 2
Polar surface area: 41.1 Å²
H-bond donors: 2
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 3
Molecule type: Small molecule
Indications: premature birth

via ChEMBL · EBI

Wikidata facts

Subclass of: chemical compound
Mass: 494.25292018799996

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Commons category: Retosiban
isomeric SMILES: CC[C@H](C)[C@@H]1C(=O)N[C@@H](C(=O)N1[C@H](c2coc(n2)C)C(=O)N3CCOCC3)C4Cc5ccccc5C4
chemical formula: C₂₇H₃₄N₄O₅
canonical SMILES: CCC(C)C1C(=O)NC(C2Cc3ccccc3C2)C(=O)N1C(C(=O)N1CCOCC1)c1coc(C)n1

Sources (3)

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Encyclopedic overview

7 sections

Contents

Mechanism of action
Pharmacology
Pharmacokinetics
Physical and chemical properties
Synthesis
See also
References

==Mechanism of action== Retosiban is a competitive oxytocin receptor antagonist which blocks the oxytocin-mediated contraction of the uterine smooth muscle in the female uterus that occurs during the initiation of preterm labour. This has been used to prevent preterm labour and premature birth.

Excerpted from Wikipedia’s “retosiban” article, available under the CC BY-SA 4.0 licence.

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