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
- CAS NO.:76721-89-6
- Empirical Formula: C12H15NO3S
- Molecular Weight: 253.32
- MDL number: MFCD00058435
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-05-04 17:34:42
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) |
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
Abamectin manufacturer
Varanous Labs Pvt Ltd
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