L-371,257

Potent and selective oxytocin receptor antagonist CAS# 162042-44-6

L-371,257

Catalog No. BCC7353----Order now to get a substantial discount!

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Chemical structure

L-371,257

3D structure

Chemical Properties of L-371,257

Cas No. 162042-44-6 SDF Download SDF
PubChem ID 6918320 Appearance Powder
Formula C28H33N3O6 M.Wt 507.59
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 10 mM in DMSO with gentle warming
Chemical Name 1-[1-[4-(1-acetylpiperidin-4-yl)oxy-2-methoxybenzoyl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one
SMILES CC(=O)N1CCC(CC1)OC2=CC(=C(C=C2)C(=O)N3CCC(CC3)N4C5=CC=CC=C5COC4=O)OC
Standard InChIKey WDERJSQJYIJOPD-UHFFFAOYSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of L-371,257

DescriptionPotent, high affinity human oxytocin (OT) receptor antagonist (Ki = 4.6 nM) that displays > 800-fold selectivity over human arginine vasopressin receptors V1a and V2. Antagonizes oxytocin-induced contractions in isolated rat uterine tissue (pA2 = 8.44) and in anesthetised rats following intravenous and intraduodenal administration. Decreases length of U-87MG cell projections induced by retinoic acid (Cat.No.0695). Orally active.

L-371,257 Dilution Calculator

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Preparing Stock Solutions of L-371,257

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9701 mL 9.8505 mL 19.7009 mL 39.4019 mL 49.2523 mL
5 mM 0.394 mL 1.9701 mL 3.9402 mL 7.8804 mL 9.8505 mL
10 mM 0.197 mL 0.985 mL 1.9701 mL 3.9402 mL 4.9252 mL
50 mM 0.0394 mL 0.197 mL 0.394 mL 0.788 mL 0.985 mL
100 mM 0.0197 mL 0.0985 mL 0.197 mL 0.394 mL 0.4925 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on L-371,257

Nonpeptide oxytocin antagonists: potent, orally bioavailable analogs of L-371,257 containing a 1-R-(pyridyl)ethyl ether terminus.[Pubmed:9873680]

Bioorg Med Chem Lett. 1998 Nov 3;8(21):3081-6.

Structure-activity studies on the oxytocin antagonist 1 (L-371,257) have identified a new series of high affinity, receptor-selective OT antagonists in which the N-acetyl-4-piperidinyl ether terminus in 1 has been replaced with a 1-(aryl)ethoxy group.

Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency.[Pubmed:10340620]

Bioorg Med Chem Lett. 1999 May 3;9(9):1311-6.

Structure-activity studies on the oxytocin antagonist 1 (L-371,257; Ki = 9.3 nM) have led to the identification of a related series of compounds containing an ortho-trifluoroethoxyphenylacetyl core which are orally bioavailable and have significantly improved potency in vitro and in vivo, e.g., compound 8 (L-374,943; Ki = 1.4 nM).

Pharmacologic characterization of the oxytocin receptor in human uterine smooth muscle cells.[Pubmed:10694212]

Br J Pharmacol. 2000 Jan;129(1):131-9.

[(3)H]-oxytocin was used to characterize the oxytocin receptor found in human uterine smooth muscle cells (USMC). Specific binding of [(3)H]-oxytocin to USMC plasma membranes was dependent upon time, temperature and membrane protein concentration. Scatchard plot analysis of equilibrium binding data revealed the existence of a single class of high-affinity binding sites with an apparent equilibrium dissociation constant (K(d)) of 0.76 nM and a maximum receptor density (B(max)) of 153 fmol mg(-1) protein. The Hill coefficient (n(H)) did not differ significantly from unity, suggesting binding to homogenous, non-interacting receptor populations. Competitive inhibition of [(3)H]-oxytocin binding showed that oxytocin and vasopressin (AVP) receptor agonists and antagonists displaced [(3)H]-oxytocin in a concentration-dependent manner. The order of potencies for peptide agonists and antagonists was: oxytocin>[Asu(1,6)]-oxytocin>AVP= atosiban>d(CH(2))(5)Tyr(Me)AVP>[Thr(4),Gly(7)]-oxytocin>dDAVP, and for nonpeptide antagonists was: L-371257>YM087>SR 49059>OPC-21268>SR 121463A>OPC-31260. Oxytocin significantly induced concentration-dependent increase in intracellular Ca(2+) concentration ([Ca(2+)](i)) and hyperplasia in USMC. The oxytocin receptor antagonists, atosiban and L-371257, potently and concentration-dependently inhibited oxytocin-induced [Ca(2+)](i) increase and hyperplasia. In contrast, the V(1A) receptor selective antagonist, SR 49059, and the V(2) receptor selective antagonist, SR 121463A, did not potently inhibit oxytocin-induced [Ca(2+)](i) increase and hyperplasia. The potency order of antagonists in inhibiting oxytocin-induced [Ca(2+)](i) increase and hyperplasia was similar to that observed in radioligand binding assays. In conclusion, these data provide evidence that the high-affinity [(3)H]-oxytocin binding site found in human USMC is a functional oxytocin receptor coupled to [Ca(2+)](i) increase and cell growth. Thus human USMC may prove to be a valuable tool in further investigation of the physiologic and pathophysiologic roles of oxytocin in the uterus. British Journal of Pharmacology (2000) 129, 131 - 139

Comparison of vasopressin binding sites in human uterine and vascular smooth muscle cells.[Pubmed:10478574]

Eur J Pharmacol. 1999 Jul 28;378(1):137-42.

Several studies indicate that oxytocin and vasopressin receptors in the human uterus are heterogeneous. We have investigated whether oxytocin and vasopressin bind to separate receptors or one class of receptors in human uterine smooth muscle cells. [3H]d(CH2)5Tyr(Me)AVP, the vasopressin V1A receptor selective radioligand, was used for comparison of vasopressin binding sites in human uterine and vascular smooth muscle cell membranes. Both membrane preparations exhibited one class of high-affinity binding sites with Kd values of 6.44 and 0.47 nM, Bmax values of 166 and 34.8 fmol/mg protein for uterine and vascular smooth muscle cells, respectively. In vascular preparations, the selective vasopressin V1A receptor antagonist, SR 49059 ((2S) 1-[(2R 3S)-(5-chloro-3-(2-chlorophenyl)- -(3.4-dimethoxybenzenesulfonyl)-3-hydroxy-2,3-dihydro-1H-indole-2- carbonyl]-pyrrolidine-2-carboxamide), showed high affinity with Ki value of 0.98 nM, confirming that these receptors belong to the vasopressin V1A receptor subtype. On the contrary, in uterine preparations, binding of [3H]d(CH2)5Tyr(Me)AVP was more effectively displaced by oxytocin and the oxytocin receptor selective antagonist, L-371257, (1-[1-[4-[ N-Acetyl-4-piperidinyl)oxy]2-methoxybenzoyl]piperidin-4-yl]- 4H-3,1-benzoxazin-2(1H)-one), than vasopressin and SR 49059, suggesting that binding may be due to cross-reaction with the oxytocin receptors. These results suggest that human uterine smooth muscle cells express only a high density of oxytocin receptors.

Description

L-371,257 is an orally bioavailable, non-blood-brain barrier penetrant, selective and competitive antagonist of oxytocin receptor (pA2=8.4) with high affinity at both the oxytocin receptor (Ki=19 nM) and vasopressin V1a receptor (Ki=3.7 nM).

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