L-371,257 | CAS#162042-44-6 | Oxytocin Receptor Antagonist

MedKoo Cat#: 532059 | Name: L-371,257

Description:

WARNING: This product is for research use only, not for human or veterinary 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.

Chemical Structure

L-371,257

CAS#162042-44-6

Theoretical Analysis

MedKoo Cat#: 532059

Name: L-371,257

CAS#: 162042-44-6

Chemical Formula: C28H33N3O6

Exact Mass: 507.2369

Molecular Weight: 507.59

Elemental Analysis: C, 66.26; H, 6.55; N, 8.28; O, 18.91

Price and Availability

Size	Price	Availability
50mg	USD 950.00	2 Weeks
100mg	USD 1,650.00	2 Weeks
200mg	USD 2,950.00	2 Weeks

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Related CAS #

No Data

Synonym

L-371,257; L 371,257; L371,257; L-371257; L 371257; L371257;

IUPAC/Chemical Name

1-[1-[4-(1-acetylpiperidin-4-yl)oxy-2-methoxybenzoyl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one

InChi Key

WDERJSQJYIJOPD-UHFFFAOYSA-N

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

SMILES Code

O=C1N(C2CCN(C(C3=CC=C(OC4CCN(C(C)=O)CC4)C=C3OC)=O)CC2)C5=CC=CC=C5CO1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

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).

In vitro activity:

Slower growth rates and lower levels of phosphorylated ERK1/2 were observed in OXTR-knockdown cells and in U-87MG cells treated with an OXTR antagonist (L-371,257). Reference: Endocr Regul. 2020 Jul 1;54(3):172-182. https://pubmed.ncbi.nlm.nih.gov/32857718/

In vivo activity:

By immunostaining tissues from OXTR-YFP knock-in mice, this study found that OXTR is expressed in a subset of Glial-like (Type I) taste cells, and also in cells on the periphery of taste buds. Using Ca2+ imaging, this study observed that physiologically appropriate concentrations of OXT (oxytocin) evoked [Ca2+]i mobilization in a subset of taste cells (EC50 approximately 33 nM). OXT-evoked responses were significantly inhibited by the OXTR antagonist, L-371,257. Reference: PLoS One. 2010 Aug 5;5(8):e11980. https://pubmed.ncbi.nlm.nih.gov/20700536/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	5.4	10.71

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 507.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Alanazi MM, Havranek T, Bakos J, Cubeddu LX, Castejon AM. Cell proliferation and anti-oxidant effects of oxytocin and oxytocin receptors: role of extracellular signal-regulating kinase in astrocyte-like cells. Endocr Regul. 2020 Jul 1;54(3):172-182. doi: 10.2478/enr-2020-0020. PMID: 32857718. 2. Sun LH, Tzeng WY, Liao YH, Deng WT, Cherng CG, Yu L. Relevance of number and physiological status of conspecifics in preventing stress-induced decreases in newly proliferated cells and neuroblasts. Psychopharmacology (Berl). 2019 Nov;236(11):3329-3339. doi: 10.1007/s00213-019-05290-4. Epub 2019 Jun 14. PMID: 31201477. 3. Sinclair MS, Perea-Martinez I, Dvoryanchikov G, Yoshida M, Nishimori K, Roper SD, Chaudhari N. Oxytocin signaling in mouse taste buds. PLoS One. 2010 Aug 5;5(8):e11980. doi: 10.1371/journal.pone.0011980. PMID: 20700536; PMCID: PMC2916830. 4. Ring RH, Malberg JE, Potestio L, Ping J, Boikess S, Luo B, Schechter LE, Rizzo S, Rahman Z, Rosenzweig-Lipson S. Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications. Psychopharmacology (Berl). 2006 Apr;185(2):218-25. doi: 10.1007/s00213-005-0293-z. Epub 2006 Jan 18. PMID: 16418825.

In vitro protocol:

In vivo protocol:

1. Sinclair MS, Perea-Martinez I, Dvoryanchikov G, Yoshida M, Nishimori K, Roper SD, Chaudhari N. Oxytocin signaling in mouse taste buds. PLoS One. 2010 Aug 5;5(8):e11980. doi: 10.1371/journal.pone.0011980. PMID: 20700536; PMCID: PMC2916830. 2. Ring RH, Malberg JE, Potestio L, Ping J, Boikess S, Luo B, Schechter LE, Rizzo S, Rahman Z, Rosenzweig-Lipson S. Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications. Psychopharmacology (Berl). 2006 Apr;185(2):218-25. doi: 10.1007/s00213-005-0293-z. Epub 2006 Jan 18. PMID: 16418825.

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. 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. 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.