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T6031

Sigma-Aldrich

DL-Thiorphan

≥98% (TLC)

Synonym(s):

(±)-N-(3-Mercapto-2-benzylpropionyl)glycine, DL-3-Mercapto-2-benzylpropanoylglycine

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About This Item

Empirical Formula (Hill Notation):
C12H15NO3S
CAS Number:
76721-89-6
Molecular Weight:
253.32
Beilstein/REAXYS Number:
4872101
MDL number:
MFCD00058435
UNSPSC Code:
12352200
PubChem Substance ID:
24278747
NACRES:
NA.77

Quality Level

200

assay

≥98% (TLC)

form

powder

mp

138 °C

solubility

ethanol: soluble 49.00-51.00 mg/mL, clear, colorless

SMILES string

OC(=O)CNC(=O)C(CS)Cc1ccccc1

InChI

1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)

InChI key

LJJKNPQAGWVLDQ-UHFFFAOYSA-N

Gene Information

human ... ACE(1636) , ECE1(1889)
rat ... Ace(24310) , Mme(24590)

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General description

Thiorphan, also called DL-mercapto-2-benzylpropanoyl-glycine is a specific and potent inhibitor of enkephalinase in nanomolar concentrations. It is an inhibitor of neutral endopeptidase. It interacts with cluster of differentiation 10 (CD10) in bone marrow cells and may modulate hematopoiesis. Thiorphan is a safe drugprescribed for diarrhea. It prevents cortical damage in newborn mice and is a potent agent for treating cerebral palsy.(CP)

Application

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.

Biochem/physiol Actions

Enkephalinase inhibitor.

Features and Benefits

This compound is featured on the Neuropeptidases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

DL-Thiorphan is soluble in ethanol at 49.00 - 51.00 mg/ml and yields a clear, colorless solution.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The enkephalinase inhibitor thiorphan shows antinociceptive activity in mice
Roques BP, et al.
Nature, 288(5788), 286-288 (1980)
Thiorphan, a neutral endopeptidase inhibitor used for diarrhoea, is neuroprotective in newborn mice
Medja F, et al.
Brain, 129(12), 3209-3223 (2006)
Global brain delivery of neprilysin gene by intravascular administration of AAV vector in mice
Iwate N, et al.
Scientific Reports (2013)
Thiorphan, an inhibitor of neutral endopeptidase/enkephalinase (CD10/CALLA) enhances cell proliferation in bone marrow cultures of patients with acute leukemia in remission
Stanovic S, et al.
Haematologia, 30(1), 1-10 (2000)
Alexander W Sauter et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 60(3), 393-399 (2018-07-14)
Patients with metastatic medullary thyroid cancer (MTC) have limited systemic treatment options. The use of radiolabeled gastrin analogs targeting the cholecystokinin-2 receptor (CCK2R) is an attractive approach. However, their therapeutic efficacy is presumably decreased by their enzymatic degradation in vivo.
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