L-368899 HCl
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MedKoo CAT#: 532058

CAS#: 160312-62-9 (HCl)

Description: L-368899 is a non-peptide and orally active oxytocin receptor antagonist that displays > 40-fold selectivity over vasopressin V1a and V2 receptors. L-368,899 HCl antagonizes oxytocin-induced uterine contractions in vitro and in vivo.

Chemical Structure

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L-368899 HCl
CAS# 160312-62-9 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 532058
Name: L-368899 HCl
CAS#: 160312-62-9 (HCl)
Chemical Formula: C26H43ClN4O5S2
Exact Mass: 590.24
Molecular Weight: 591.223
Elemental Analysis: C, 52.82; H, 7.33; Cl, 6.00; N, 9.48; O, 13.53; S, 10.85

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 Weeks
10mg USD 650 2 Weeks
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Related CAS #: 148927-60-0 (free base)   160312-62-9 (HCl)    

Synonym: L-368,899 HCl; L-368,899; L-368,899; L-368,899; L-368899; L-368899; L-368899.

IUPAC/Chemical Name: 1-((7,7-Dimethyl-2(S)-(2(S)-amino-4-(methylsulfonyl)butyramido)bicyclo[2,2,1]heptan-1(S)-yl)methylsulfonyl)-4-(2-methylphenyl)piperazine hydrochloride

InChi Key: GIUFQWFJHXXXEQ-SYENMOKSSA-N

InChi Code: InChI=1S/C26H42N4O5S2.ClH/c1-19-7-5-6-8-22(19)29-12-14-30(15-13-29)37(34,35)18-26-11-9-20(25(26,2)3)17-23(26)28-24(31)21(27)10-16-36(4,32)33;/h5-8,20-21,23H,9-18,27H2,1-4H3,(H,28,31);1H/t20?,21-,23-,26+;/m0./s1

SMILES Code: CC1=CC=CC=C1N2CCN(S(=O)(C[C@@]3(C4(C)C)[C@@H](NC([C@@H](N)CCS(=O)(C)=O)=O)CC4CC3)=O)CC2.[H]Cl

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:
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Biological target: -368,899 hydrochloride is a potent, selective, orally bioavailable, non-peptide Oxytocin Receptor antagonist, with IC50s of 8.9 nM and 26 nM for rat uterus and human uterus oxytocin receptor, respectively.
In vitro activity: Compound 7 (L-368,899) exhibited the best overall profile of OT receptor affinity (IC50 = 8.9 nM, rat uterus; 26 nM, human uterus), potency for inhibition of OT-stimulated contractions of the isolated rat uterus (pA2 = 8.9) and in situ rat uterus (AD50 = 0.35 mg/kg after intravenous (i.v.) administration and 7.0 mg/kg after intraduodenal administration), aqueous solubility (3.7 mg/mL at pH 5.0), and oral bioavailability in several species (35% (rat), 25% (dog), and 21% (chimpanzee) as estimated from radioreceptor determination of drug levels in plasma after oral and i.v. dosing). Reference: J Med Chem. 1994 Mar 4;37(5):565-71. https://pubmed.ncbi.nlm.nih.gov/8126695/
In vivo activity: Compound 7 (L-368,899) exhibited the best overall profile of OT receptor affinity (IC50 = 8.9 nM, rat uterus; 26 nM, human uterus), potency for inhibition of OT-stimulated contractions of the isolated rat uterus (pA2 = 8.9) and in situ rat uterus (AD50 = 0.35 mg/kg after intravenous (i.v.) administration and 7.0 mg/kg after intraduodenal administration), aqueous solubility (3.7 mg/mL at pH 5.0), and oral bioavailability in several species (35% (rat), 25% (dog), and 21% (chimpanzee) as estimated from radioreceptor determination of drug levels in plasma after oral and i.v. dosing). Reference: J Med Chem. 1994 Mar 4;37(5):565-71. https://pubmed.ncbi.nlm.nih.gov/8126695/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 94.6 159.94
Water 54.6 92.28

Preparing Stock Solutions

The following data is based on the product molecular weight 591.22 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.

Recalculate based on batch purity %
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. Williams PD, Anderson PS, Ball RG, Bock MG, Carroll L, Chiu SH, Clineschmidt BV, Culberson JC, Erb JM, Evans BE, et al. 1-((7,7-Dimethyl-2(S)-(2(S)-amino-4-(methylsulfonyl)butyramido)bicyclo [2.2.1]-heptan-1(S)-yl)methyl)sulfonyl)-4-(2-methylphenyl)piperaz ine (L-368,899): an orally bioavailable, non-peptide oxytocin antagonist with potential utility for managing preterm labor. J Med Chem. 1994 Mar 4;37(5):565-71. doi: 10.1021/jm00031a004. PMID: 8126695.
In vitro protocol: 1. Williams PD, Anderson PS, Ball RG, Bock MG, Carroll L, Chiu SH, Clineschmidt BV, Culberson JC, Erb JM, Evans BE, et al. 1-((7,7-Dimethyl-2(S)-(2(S)-amino-4-(methylsulfonyl)butyramido)bicyclo [2.2.1]-heptan-1(S)-yl)methyl)sulfonyl)-4-(2-methylphenyl)piperaz ine (L-368,899): an orally bioavailable, non-peptide oxytocin antagonist with potential utility for managing preterm labor. J Med Chem. 1994 Mar 4;37(5):565-71. doi: 10.1021/jm00031a004. PMID: 8126695.
In vivo protocol: 1. Williams PD, Anderson PS, Ball RG, Bock MG, Carroll L, Chiu SH, Clineschmidt BV, Culberson JC, Erb JM, Evans BE, et al. 1-((7,7-Dimethyl-2(S)-(2(S)-amino-4-(methylsulfonyl)butyramido)bicyclo [2.2.1]-heptan-1(S)-yl)methyl)sulfonyl)-4-(2-methylphenyl)piperaz ine (L-368,899): an orally bioavailable, non-peptide oxytocin antagonist with potential utility for managing preterm labor. J Med Chem. 1994 Mar 4;37(5):565-71. doi: 10.1021/jm00031a004. PMID: 8126695.

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1: Smith AL, Freeman SM, Voll RJ, Young LJ, Goodman MM. Carbon-11 N-methyl alkylation of L-368,899 and in vivo PET imaging investigations for neural oxytocin receptors. Bioorg Med Chem Lett. 2013 Feb 1;23(3):902-6. doi: 10.1016/j.bmcl.2012.10.116. PubMed PMID: 23270988; PubMed Central PMCID: PMC3756487.

2: Mann GE, Lamming GE, Scholey D, Hunter M, Pettibone DJ. Attenuation of PGF2alpha release in ewes infused with the oxytocin antagonist L-368,899. Domest Anim Endocrinol. 2003 Oct;25(3):255-62. PubMed PMID: 14550509.

3: Matuszewski BK, Chavez-Eng CM, Constanzer ML. Development of high-performance liquid chromatography-tandem mass spectrometric methods for the determination of a new oxytocin receptor antagonist (L-368,899) extracted from human plasma and urine: a case of lack of specificity due to the presence of metabolites. J Chromatogr B Biomed Sci Appl. 1998 Sep 25;716(1-2):195-208. PubMed PMID: 9824233.

4: Thompson KL, Vincent SH, Miller RR, Colletti AE, Alvaro RF, Wallace MA, Feeney WP, Chiu SH. Pharmacokinetics and disposition of the oxytocin receptor antagonist L-368,899 in rats and dogs. Drug Metab Dispos. 1997 Oct;25(10):1113-8. PubMed PMID: 9321512.

5: Williams PD, Anderson PS, Ball RG, Bock MG, Carroll L, Chiu SH, Clineschmidt BV, Culberson JC, Erb JM, Evans BE, et al. 1-((7,7-Dimethyl-2(S)-(2(S)-amino-4-(methylsulfonyl)butyramido)bicyclo [2.2.1]-heptan-1(S)-yl)methyl)sulfonyl)-4-(2-methylphenyl)piperaz ine (L-368,899): an orally bioavailable, non-peptide oxytocin antagonist with potential utility for managing preterm labor. J Med Chem. 1994 Mar 4;37(5):565-71. PubMed PMID: 8126695.