A nonpeptide oxytocin receptor antagonist
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L-371,257

Item No. 42436

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[1-[4-[(1-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]-4-piperidinyl]-1,4-dihydro-2H-3,1-benzoxazin-2-one
CAS Number
162042-44-6
Molecular Formula
C28H33N3O6
Formula Weight
507.6
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly Soluble: 0.1-1 mg/mL
SMILES
O=C1OCC2=C(N1C3CCN(CC3)C(C4=C(OC)C=C(C=C4)OC5CCN(CC5)C(C)=O)=O)C=CC=C2
InChi Code
InChI=1S/C28H33N3O6/c1-19(32)29-15-11-22(12-16-29)37-23-7-8-24(26(17-23)35-2)27(33)30-13-9-21(10-14-30)31-25-6-4-3-5-20(25)18-36-28(31)34/h3-8,17,21-22H,9-16,18H2,1-2H3
InChi Key
WDERJSQJYIJOPD-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $28

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    5 mg

    $104

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    10 mg

    $180

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    25 mg

    $413

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    Product Description

    L-371,257 is a nonpeptide oxytocin receptor antagonist (Ki = 19 and 4.6 nM for the rat uterine and human uterine receptors, respectively).1 It is selective for oxytocin receptors over human arginine vasopressin (AVP) receptors V1A and -V2 (Kis = 3,200 and >10,000 nM for the human platelet and kidney receptors, respectively) and rat AVP receptor V2 (Ki = >10,000 nM for the rat kidney receptor) but also inhibits rat AVP receptor V1A (Ki = 3.7 nM for the rat liver receptor). L-371,257 inhibits spontaneous contractions in isolated human myometrial strips (IC50 = 71 pM).2 It inhibits oxytocin-induced uterine contractions in rats (ED50 = 0.55 mg/kg).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Williams, P.D., Clineschmidt, B.V., Erb, J.M., et al. 1-(1-[4-[(N-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]piperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): A new, orally bioavailable, non-peptide oxytocin antagonist. J. Med. Chem. 38(23), 4634-4636 (1998).

    2. Wilson, R.J., Allen, M.J., Nandi, M., et al. Spontaneous contractions of myometrium from humans, non-human primate and rodents are sensitive to selective oxytocin receptor antagonism in vitro. BJOG 108(9), 960-966 (2001).