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HomeProduct name listDL-THIORPHAN

DL-THIORPHAN

Synonym(s):(±)-N-(3-Mercapto-2-benzylpropionyl)glycine;DL-3-Mercapto-2-benzylpropanoylglycine;DL-Thiorphan - CAS 76721-89-6 - Calbiochem;N-[(RS)-2-Benzyl-3-mercaptopropanoyl]-glycine

DL-THIORPHAN Structural

What is DL-THIORPHAN?

Chemical properties

Off-White Solid

The Uses of DL-THIORPHAN

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.

The Uses of DL-THIORPHAN

An Enkephalinase inhibitor

The Uses of DL-THIORPHAN

The active metabolite

The Uses of DL-THIORPHAN

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.

What are the applications of Application

Thiorphan (DL) is an enkephalinase and metalloproteinase inhibitor

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

Properties of DL-THIORPHAN

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 for DL-THIORPHAN

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P330:Rinse mouth.
P362:Take off contaminated clothing and wash before reuse.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.
P405:Store locked up.
P403+P233:Store in a well-ventilated place. Keep container tightly closed.
P501:Dispose of contents/container to..…

Computed Descriptors for DL-THIORPHAN

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