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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

Signal Word

Warning

Hazard Statements

H361fd

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
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
Complement Components Showed a Time-Dependent Local Expression Pattern in Constant and Acute White Light-Induced Photoreceptor Damage.
Nicole Schäfer et al.
Frontiers in molecular neuroscience, 10, 197-197 (2017-07-06)
Yu-Ping Lin et al.
Molecular cell, 70(2), 228-241 (2018-04-21)
The house dust mite is the principal source of perennial aeroallergens in man. How these allergens activate innate and adaptive immunity is unclear, and therefore, there are no therapies targeting mite allergens. Here, we show that house dust mite extract
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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