For research use only. Not for therapeutic Use.
L-371,257 is a potent, high affinity human oxytocin (OT) receptor antagonist (Ki = 4.6 nM) that displays > 800-fold selectivity over human arginine vasopressin receptors V1a and V2. L-371,257 antagonizes oxytocin-induced contractions in isolated rat uterine tissue (pA2 = 8.44) and in anesthetised rats following intravenous and intraduodenal administration.
| Catalog Number | M036158 |
| CAS Number | 162042-44-6 |
| Synonyms | 1-(1-(4-((1-acetylpiperidin-4-yl)oxy)-2-methoxybenzoyl)piperidin-4-yl)-1H-benzo[d][1,3]oxazin-2(4H)-one |
| Molecular Formula | C28H33N3O6 |
| Purity | ≥95% |
| Target | Oxytocin Receptor |
| Solubility | Soluble in DMSO > 10 mM |
| Storage | Store at RT |
| IUPAC Name | 1-[1-[4-(1-acetylpiperidin-4-yl)oxy-2-methoxybenzoyl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one |
| InChI | 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 |
| InChIKey | WDERJSQJYIJOPD-UHFFFAOYSA-N |
| SMILES | CC(=O)N1CCC(CC1)OC2=CC(=C(C=C2)C(=O)N3CCC(CC3)N4C5=CC=CC=C5COC4=O)OC |
| Reference | </br>1: Williams PD, Bock MG, Evans BE, Freidinger RM, Gallicchio SN, Guidotti MT, Jacobson MA, Kuo MS, Levy MR, Lis EV, Michelson SR, Pawluczyk JM, Perlow DS, Pettibone DJ, Quigley AG, Reiss DR, Salvatore C, Stauffer KJ, Woyden CJ. Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency. Bioorg Med Chem Lett. 1999 May 3;9(9):1311-6. PubMed PMID: 10340620.</br>2: Kuo MS, Bock MG, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, Perlow DS, Pettibone DJ, Quigley AG, Reiss DR, Williams PD, Woyden CJ. Nonpeptide oxytocin antagonists: potent, orally bioavailable analogs of L-371,257 containing a 1-R-(pyridyl)ethyl ether terminus. Bioorg Med Chem Lett. 1998 Nov 3;8(21):3081-6. PubMed PMID: 9873680.</br>3: Williams PD, Clineschmidt BV, Erb JM, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, Pettibone DJ, Reiss DR, Veber DF, 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. 1995 Nov 10;38(23):4634-6. PubMed PMID: 7473590.</br></br> |
