Thiorphan
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Thiorphan
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CAS No:
76721-89-6
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Formula:
C12H15NO3S
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Chemical Name:
Thiorphan
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Synonyms:
Glycine,N-[2-(mercaptomethyl)-1-oxo-3-phenylpropyl]-;Glycine,N-[2-(mercaptomethyl)-1-oxo-3-phenylpropyl]-,(±)-;N-[2-(Mercaptomethyl)-1-oxo-3-phenylpropyl]glycine;Thiorphan;(±)-Thiorphan;DL-Thiorphan;2-[(2-Benzyl-3-sulfanylpropanoyl)amino]acetic acid;107672-11-7;225661-76-7
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CAS No:
Description
Off-White Solid
Thiorphan is a N-acyl-amino acid.|A potent inhibitor of membrane metalloendopeptidase (ENKEPHALINASE). Thiorphan potentiates morphine-induced ANALGESIA and attenuates naloxone-precipitated withdrawal symptoms.
Characteristics
67.4
1.37
off-white solid
1.2±0.1 g/cm3
138-140 °C
524.0±50.0 °C at 760 mmHg
270.7±30.1 °C
1.577
ethanol: 50 mg/mL, clear, colorless
-15°C
Drug Information
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)
(3-Mercapto-2-benzylpropionyl)glycine
Thiorphan Use and Manufacturing
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.
Computed Properties
Molecular Weight:253.32
XLogP3:1.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:253.07726451
Monoisotopic Mass:253.07726451
Topological Polar Surface Area:67.4
Heavy Atom Count:17
Complexity:265
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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