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76721-89-6

76721-89-6 Structure

76721-89-6 Structure
IdentificationBack Directory
[Name]

DL-THIORPHAN
[CAS]

76721-89-6
[Synonyms]

C01619
THIORPHAN
DL-THIORPHAN
Thiorphan-d5
THIORPHAN (DL)
Bisoprolol FuMarate IMpurity-Q
(DL-3-MERCAPTO-2-BENZYLPROPANOYL)-GLY
DL-3-MERCAPTO-2-BENZYLPROPANOYL-GLYCINE
(DL-3-MERCAPTO-2-BENZYLPROPANOYL)-GLY-OH
((RS)-2-BENZYL-3-MERCAPTOPROPIONYL)-GLY-OH
((RS)-2-BENZYL-3-MERCAPTOPROPIONYL)-GLYCINE
N-[(RS)-2-BENZYL-3-MERCAPTOPROPANOYL]-GLYCINE
(+/-)-N-(3-MERCAPTO-2-BENZYLPROPIONYL)GLYCINE
2-(2-benzyl-3-MercaptopropanaMido)acetic acid
N-ALPHA-(DL-3-MERCAPTO-2-BENZYLPROPANOYL)-GLYCINE
rac-N-[(2R*)-3-Mercapto-2-benzylpropionyl]glycine
2-MercaptoMethyl-3-phenylpropionylaMinoacetic Acid
N-[2-(MercaptoMethyl)-1-oxo-3-phenylpropyl]glycine
2-[[2-(Benzyl)-3-sulfanylpropanoyl]aMino]acetic acid
(DL-3-Mercapto-2-benzylpropionyl)-Gly-OH, (DL-3-Mercapto-2-benzylpropanoyl)-Gly-OH
(±)-N-(3-Mercapto-2-benzylpropionyl)glycine, DL-3-Mercapto-2-benzylpropanoylglycine
2-Mercaptomethyl-3-phenyl-propionylamino-acetic Acid, D,L-3-Mercapto-2-benzylpropanoylglycine,
[Molecular Formula]

C12H15NO3S
[MDL Number]

MFCD00058435
[MOL File]

76721-89-6.mol
[Molecular Weight]

253.32
Chemical PropertiesBack Directory
[Appearance]

Off-White Solid
[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
Hazard InformationBack Directory
[Chemical Properties]

Off-White Solid
[Uses]

An Enkephalinase inhibitor
[Uses]

The active metabolite
[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.
[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
Safety DataBack Directory
[Safety Statements ]

22-24/25
[WGK Germany ]

3
[F ]

10
[HS Code ]

29309090
Spectrum DetailBack Directory
[Spectrum Detail]

DL-THIORPHAN(76721-89-6)1HNMR
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