DL-THIORPHAN Chemical Properties

Melting point:

138-140 °C

Boiling point:

524.0±50.0 °C(Predicted)

Density 

1.246±0.06 g/cm3(Predicted)

RTECS 

MC0596440

storage temp. 

-15°C

solubility 

ethanol: 50 mg/mL, clear, colorless

form 

White solid

pka

3.48±0.10(Predicted)

color 

White to Off-White

BRN 

4872101

CAS DataBase Reference

76721-89-6

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

10

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich

DL-THIORPHAN Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

An Enkephalinase inhibitor

Uses

Thiorphan is a potent inhibitor of neprilysin, a membrane metallo-endopeptidase that cleaves peptide hormones, such as enkephalins, glucagon, and bradykinin (Ki = 4-140 nM). It is much less effective against neprilysin-2 (IC50 = 22.1 μM), angiotensin-converting enzyme, and endothelin-converting enzyme-1. Thiorphan can be produced in vivo via the metabolism of the prodrug acetorphan. Neprilysin is overexpressed in many forms of cancer and may play a role in protecting against Alzheimer’s disease.

Uses

DL-Thiorphan has been used to evaluate the activity of NEP-dependent neutral endopeptidase. DL-Thiorphan has also been used for determining NEP enzymatic activity using fluorimetric assays.

Uses

The active metabolite

Definition

ChEBI: Thiorphan is a N-acyl-amino acid.

General Description

A thiol-containing amido-acid that selectively binds to the active site zinc of neprilysin (also known as neutral endopeptidase and NEP) and inhibits its activity (IC₅₀ = 2.1 nM). Inhibits the β-amyloid (Aβ) degrading activity of neprilysin in vivo, but does not affect the secretion of either Aβ peptide or amyloid precursor protein (APP). Also shown to inhibit other neprilysin-related family members, such as mouse NL1 (IC₅₀ = 47 nM) and the neprilysin homolog from Ascaris suum (IC₅₀ = 22 μM). Inhibits the activity of angiotensin-converting enzyme (ACE) (IC₅₀ = 140 nM), but has no effect on the activity of endothelin-converting enzyme (ECE).

Biochem/physiol Actions

Primary TargetNEP activity

DL-THIORPHAN(76721-89-6)Related Product Information

• Zinc glycinate
• Ferrous Bisglycinate
• Trimethylglycine
• Glycine
• Benzylmalonic acid
• Deacetyl Racecadotril Disulfide
• Benzyl glycinate p-toluenesulfonate
• ACETYL SULFIDE
• Thiorphan Disulfide
• Diethyl benzylmalonate
• Racecadotril Diacid Impurity
• Racecadotril
• N-P-TOSYLGLYCINE BENZYL ESTER
• Thioacetic acid
• Glycine, N-[1-oxo-2-(phenylmethyl)-3-[(1-thioxoethyl)thio]propyl]-, phenylmethyl ester
• 2-Benzylacrylic acid
• Acrylic acid
• Racecadotril Impurity 14