76721-89-6

Basic information

• Product Name: DL-THIORPHAN
• Synonyms: N-[(RS)-2-BENZYL-3-MERCAPTOPROPANOYL]-GLYCINE;(+/-)-N-(3-MERCAPTO-2-BENZYLPROPIONYL)GLYCINE;N-ALPHA-(DL-3-MERCAPTO-2-BENZYLPROPANOYL)-GLYCINE;THIORPHAN;THIORPHAN (DL);((RS)-2-BENZYL-3-MERCAPTOPROPIONYL)-GLYCINE;((RS)-2-BENZYL-3-MERCAPTOPROPIONYL)-GLY-OH;2-Mercaptomethyl-3-phenyl-propionylamino-acetic Acid, D,L-3-Mercapto-2-benzylpropanoylglycine,
• CAS NO: 76721-89-6
• Molecular Formula: C₁₂H₁₅NO₃S
• Molecular Weight: 253.32
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Inhibitors;Sulfur & Selenium Compounds;Aromatics
• Mol File: 76721-89-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 138-140 °C
• Boiling Point: 524 °C at 760 mmHg
• Flash Point: 270.7 °C
• Appearance: off-white solid
• Density: 1.246 g/cm³
• Vapor Pressure: 3.94E-08mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: -15°C
• Solubility: ethanol: 50 mg/mL, clear, colorless
• PKA: 3.48±0.10(Predicted)
• BRN: 4872101
• CAS DataBase Reference: DL-THIORPHAN(CAS DataBase Reference)
• NIST Chemistry Reference: DL-THIORPHAN(76721-89-6)
• EPA Substance Registry System: DL-THIORPHAN(76721-89-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: MC0596440
• F: 10
• Hazardous Substances Data: 76721-89-6(Hazardous Substances Data)

Usage

Description

DL-THIORPHAN is a synthetic enkephalinase inhibitor that acts as a potent inhibitor of neprilysin, a membrane metallo-endopeptidase responsible for cleaving peptide hormones such as enkephalins, glucagon, and bradykinin. It is produced in vivo through the metabolism of the prodrug acetorphan and has a Ki value ranging from 4-140 nM. DL-THIORPHAN is less effective against neprilysin-2, angiotensin-converting enzyme, and endothelin-converting enzyme-1. Neprilysin is overexpressed in many forms of cancer and may play a role in protecting against Alzheimer's disease.

Uses

Used in Pharmaceutical Industry:
DL-THIORPHAN is used as an enkephalinase inhibitor for its ability to block the degradation of peptide hormones, which can have potential therapeutic applications in various conditions.
Used in Cancer Research:
DL-THIORPHAN is used as a research tool to evaluate the activity of NEP-dependent neutral endopeptidase, which is overexpressed in many forms of cancer. Understanding the role of neprilysin in cancer may lead to the development of targeted therapies.
Used in Alzheimer's Disease Research:
DL-THIORPHAN is used as a research tool for determining NEP enzymatic activity using fluorimetric assays, which can help in understanding the role of neprilysin in protecting against Alzheimer's disease and potentially developing treatments for this condition.

Biochem/physiol Actions

Primary TargetNEP activity

InChI:InChI=1/C12H15NO3S/c13-10(12(15)16)11(14)9(7-17)6-8-4-2-1-3-5-8/h1-5,9-10,17H,6-7,13H2,(H,15,16)

Upstream product

• 81110-05-6 N-[S-Acetyl-2'-benzyl-3'-mercaptopropionyl]glycine methyl ester 

Relevant articles and documents

AMINOACID DERIVATIVES AND THEIR THERAPEUTIC APPLICATIONS

This invention relates to aminoacid derivatives, and compositions containing the same and having enkephalinase-inhibiting, antalgic, antidiarrhea and hypotensive activities, of the formula STR1 whose variables are as set forth herein, for example STR2