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N0289

Sigma-Aldrich

Nafamostat mesylate

≥98% (HPLC), powder, serine protease inhibitor

Synonym(s):

4-[(Aminoiminomethyl)amino]benzoic acid 6-(aminoiminomethyl)-2-naphthalenyl ester dimethanesulfonate, FUT-175

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About This Item

Empirical Formula (Hill Notation):
C19H17N5O2 · 2CH4O3S
CAS Number:
82956-11-4
Molecular Weight:
539.58
MDL number:
MFCD00941430
UNSPSC Code:
51111800
PubChem Substance ID:
329818423
NACRES:
NA.77

product name

Nafamostat mesylate, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear
H2O: >10 mg/mL

storage temp.

room temp

SMILES string

CS(O)(=O)=O.CS(O)(=O)=O.NC(=N)Nc1ccc(cc1)C(=O)Oc2ccc3cc(ccc3c2)C(N)=N

InChI

1S/C19H17N5O2.2CH4O3S/c20-17(21)14-2-1-13-10-16(8-5-12(13)9-14)26-18(25)11-3-6-15(7-4-11)24-19(22)23;2*1-5(2,3)4/h1-10H,(H3,20,21)(H4,22,23,24);2*1H3,(H,2,3,4)

InChI key

SRXKIZXIRHMPFW-UHFFFAOYSA-N

Application

Nafamostat mesylate has been used:
  • as a serine protease inhibitor to study its effects on proteolytic degradation of therapeutic proteins recombinantly expressed in Chinese hamster ovary (CHO)-K1-derived cells
  • to stop complement activation to validate the assay for murine C3 fragments
  • as a serine protease inhibitor to study its effects on house dust mite extract evoked Ca2+ entry

Biochem/physiol Actions

Nafamostat mesylate is a broad spectrum serine protease inhibitor, kallikrein inhibitor, and inhibits blood coagulation. It is also a possible complement inhibitor.
Nafamostat mesylate is used in the treatment of disseminated intravascular coagulation (DIC), pancreatitis, and systemic inflammatory response syndrome. It can block the proliferation, adhesion, and invasion of cancer cells and repress tumor progression in animal models. Nafamostat mesylate is involved in the development of immune activity. In combination with favipiravir, nafamostat mesylate may block virus entry and replication, and inhibit the pathogenic host response. This combination treatment might be effective for critically ill Covid-19 patients.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361fd

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

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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Claire Rolland-Fourcade et al.
Gut, 66(10), 1767-1778 (2017-01-18)
Proteases are key mediators of pain and altered enteric neuronal signalling, although the types and sources of these important intestinal mediators are unknown. We hypothesised that intestinal epithelium is a major source of trypsin-like activity in patients with IBS and
Nafamostat Mesylate Blocks Activation of SARS-CoV-2: New Treatment Option for COVID-19.
Markus Hoffmann et al.
Antimicrobial agents and chemotherapy, 64(6) (2020-04-22)
Jean-Baptiste Coty et al.
Electrophoresis, 37(17-18), 2401-2409 (2016-07-09)
Crossed immunoelectrophoresis (C-IE) is used to detect and quantify specific proteins. An application allowed the evaluation of complement system activation by nanomaterials. The work aimed to improve the C-IE toward a higher throughput and less tedious method. A new concept
Xi Chen et al.
Frontiers in oncology, 9, 852-852 (2019-09-26)
Nafamostat mesylate (NM), a synthetic serine protease inhibitor first placed on the market by Japan Tobacco in 1986, has been approved to treat inflammatory-related diseases, such as pancreatitis. Recently, an increasing number of studies have highlighted the promising effects of
Catherine Martel et al.
PloS one, 6(4), e18812-e18812 (2011-04-29)
The activation of complement during platelet activation is incompletely understood. We sought to explore the formation of C5b-9 and anaphylatoxins binding to collagen-activated platelets. C5b-9, anaphylatoxins C3a, C4a and C5a, and anaphylatoxin receptors C3aR1 and C5aR were measured by flow
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