Thiorphan (DL) An enkephalinase and metalloproteinase inhibitor

Thiorphan (DL) (CAS 76721-89-6)

Thiorphan (DL) | CAS 76721-89-6 is rated 5.0 out of 5 by 1.
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Synonym: DL-Thiorphan; (±)-N-(3-Mercapto-2-benzylpropionyl)glycine; DL-3-Mercapto-2-benzylpropanoylglycine
Application: An enkephalinase and metalloproteinase inhibitor
CAS Number: 76721-89-6
Purity: >97%
Molecular Weight: 253.3
Molecular Formula: C12H15NO3S
* Refer to Certificate of Analysis for lot specific data (including water content).
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Thiorphan is a enkephalinase (CD10) and metalloproteinase (MMP) inhibitor that displays antinociceptive activity. The compound can inhibit neutral endopeptidase CD10 and has antiapoptotic and proliferative protective effects. Research shows that thiorphan has the ability to block the degradation of the luteinizing hormone releasing hormone (LHRH). At higher concentrations, (14 μM) this compound has been shown to inhibit the activity of angiotensin-converting enzyme (ACE).


References

1. Roques, B.P., et al. 1980. Nature. 288: 286-288. PMID: 7001254
2. Reche, I., et al. 1998. Neuropharmacology. 37: 215-222. PMID: 9680246
3. Yang, X., et al. 1998. Pharm. Res. 15: 1480-1484. PMID: 9755904
4. Eriksson, U., et al. 2005. J. Biotechnol. 119: 76-86. PMID: 16046243
5. Amantini, C., et al. 2008. J. Pharmacol. Exp. Ther. 327: 215-225. PMID: 18621988

Physical State :
Solid
Solubility :
Soluble in ethanol (50 mg/ml), a mixture of methanol , chloroform (1:1) (50 mg/ml), DMSO, and methanol. Insoluble in water.
Storage :
Store at -20° C
Melting Point :
138° C
Boiling Point :
~524.0° C at 760 mmHg (Predicted)
Density :
~1.2 g/cm3 (Predicted)
Refractive Index :
n20D 1.58
IC50 :
NEP : IC50 = 2.1 nM; ACE: IC50 = 14 nM
Ki Data :
Neprilysin: Ki= 4.7 nM (human); Neprilysin: Ki= 40 nM (Rattus norvegicus)
pK Values :
pKa: 3.48
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
MC0596440
PubChem CID :
3132
MDL Number :
MFCD00058435
Beilstein Registry :
4872101
SMILES :
C1=CC=C(C=C1)CC(CS)C(=O)NCC(=O)O

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Certificate of Analysis

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Thiorphan (DL)  Product Citations

See how others have used Thiorphan (DL). Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 28450206  Deng, J. et al. 2017. J Control Release. 255: 202-209.

PMID: # 25925093  2015. J. Neurovirol. 21: 480-90.

PMID: # 24085318  2013. Inflamm. Res. 62: 1053-61.

Citations 1 to 3 of 3 total
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Rated 5 out of 5 by from Eriksson et al Eriksson et al. (PubMed ID 16046243) used thiorphan (DL) to inactivate metalloproteinase activity involved in autocrine regulation of Trichoplusia ni cell proliferation. -SCBT Publication Review
Date published: 2015-03-18
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