Nafamostat
PubChem CID
4413
Structure
Molecular Formula
Synonyms
- Nafamostat
- 81525-10-2
- Nafamostat [INN]
- Nafamstat
- (6-carbamimidoylnaphthalen-2-yl) 4-(diaminomethylideneamino)benzoate
Molecular Weight
347.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-03-25
- Modify:2025-02-01
Description
Nafamostat is a member of benzoic acids and a member of guanidines.
Nafamostat is a synthetic serine protease inhibitor that is commonly formulated with hydrochloric acid due to its basic properties. It has been used in trials studying the prevention of Liver Transplantation and Postreperfusion Syndrome. The use of nafamostat in Asian countries is approved as an anticoagulant therapy for patients undergoing continuous renal replacement therapy due to acute kidney injury.
Nafamostat is a broad-spectrum, synthetic serine protease inhibitor, with anticoagulant, anti-inflammatory, mucus clearing, and potential antiviral activities. Upon administration, nafamostat inhibits the activities of a variety of proteases, including thrombin, plasmin, kallikrein, trypsin, and Cl esterase in the complement system, and factors VIIa, Xa, and XIIa in the coagulation system. Although the mechanism of action of nafamostat is not fully understood, trypsinogen activation in the pancreas is known to be a trigger reaction in the development of pancreatitis. Nafamostat blocks the activation of trypsinogen to trypsin and the inflammatory cascade that follows. Nafamostat may also decrease epithelial sodium channel (ENaC) activity and increase mucus clearance in the airways. ENaC activity is increased in cystic fibrosis. In addition, nafamostat may inhibit the activity of transmembrane protease, serine 2 (TMPRSS2), a host cell serine protease that mediates viral cell entry for influenza virus and coronavirus, thereby inhibiting viral infection and replication.
Chemical Structure Depiction
(6-carbamimidoylnaphthalen-2-yl) 4-(diaminomethylideneamino)benzoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C19H17N5O2/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/h1-10H,(H3,20,21)(H4,22,23,24)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
MQQNFDZXWVTQEH-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C1=CC(=CC=C1C(=O)OC2=CC3=C(C=C2)C=C(C=C3)C(=N)N)N=C(N)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C19H17N5O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 6'-amidino-2-naphthyl 4-guanidinobenzoate
- 6'-amidino-2-naphthyl 4-guanidinobenzoate, dimethanesulfonate
- Benzoic acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl ester
- Benzoic acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl ester, dihydrochloride
- Benzoic acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl ester, dimethanesulfonate
- CKD-314
- CKD314
- FUT 175
- FUT-175
- nafamostat
- nafamostat dihydrochloride
- nafamostat mesilate
- nafamostat mesylate
- nafamstat mesilate
- Ronastat
- Nafamostat
- 81525-10-2
- Nafamostat [INN]
- Nafamstat
- (6-carbamimidoylnaphthalen-2-yl) 4-(diaminomethylideneamino)benzoate
- CHEMBL273264
- Y25LQ0H97D
- p-Guanidinobenzoic acid ester with 6-hydroxy-2-naphthamidine
- 6-carbamimidoylnaphthalen-2-yl 4-guanidinobenzoate
- Nafamostat (INN)
- Benzoic acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl ester
- Benzoic acid, 4-[(aminoiminomethyl)amino]-,6-(aminoiminomethyl)-2-naphthalenyl ester
- Nafamostatum [Latin]
- (6-carbamimidoylnaphthalen-2-yl) 4-carbamimidamidobenzoate
- Nafamostatum
- CKD-314
- NCGC00160398-01
- 6-Amidino2-naphthyl 4-guanidinobenzoate
- UNII-Y25LQ0H97D
- Nafabelltan
- NAFAMOSTAT [MI]
- 6-(Aminoiminomethyl)-2-naphthalenyl 4-((aminoiminomethyl)amino)benzoate
- NAFAMOSTAT [WHO-DD]
- BSPBio_001194
- SCHEMBL135503
- CKD314
- GTPL4262
- DTXSID0048420
- CHEBI:135466
- HMS3742K19
- ALBB-027243
- BCP13085
- HY-B0190
- BDBM50063698
- AKOS017259237
- DB12598
- 6-amidino-2-naphthyl p-guanidinobenzoate
- NCGC00160398-02
- NCGC00160398-03
- NCGC00160398-04
- NCGC00160398-13
- BS-17665
- FUT-175; FUT 175; FUT175
- NS00069533
- D08240
- G78310
- MLS-0435512.0001
- AB01566816_01
- BRD-K06674495-334-03-2
- BRD-K06674495-334-04-0
- Q15409374
- 4-Guanidino-benzoic acid 6-carbamimidoyl-naphthalen-2-yl ester
- 6-carbamimidoylnaphthalen-2-yl 4-[(diaminomethylidene)amino]benzoate
- 4-Guanidino-benzoic acid 6-carbamimidoyl-naphthalen-2-yl ester(FUT-175)
- 7RF
- benzoic acid, 4-[(aminoiminomethyl)amino]-, 6-(aminoiminomethyl)-2-naphthalenyl ester, methanesulfonate (1:2)
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
347.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
347.13822480 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
347.13822480 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
141 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
26
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
552
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Pharmaceutical
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Used as an anticoagulant in patients with disseminative blood vessel coagulation, hemorrhagic lesions, and hemorrhagic tendencies. It prevents blood clot formation during extracorporeal circulation in patients undergoing continuous renal replacement therapy and extra corporeal membrane oxygenation.
Nafamostat is a fast-acting proteolytic inhibitor used during hemodialysis to prevent the proteolysis of fibrinogen into fibrin by competitively inhibiting several serine proteases including thrombin. It improves acute pancreatitis and prevents blood clot formation during extracorporeal circulation and has an anti-inflammatory effect in vitro. A study suggets that nafamostat has a neuroprotective role during ischemia-induced brain injury from antithrombin activity.
Anticoagulants
Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)
Serine Proteinase Inhibitors
Exogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES. (See all compounds classified as Serine Proteinase Inhibitors.)
Trypsin Inhibitors
Serine proteinase inhibitors which inhibit trypsin. They may be endogenous or exogenous compounds. (See all compounds classified as Trypsin Inhibitors.)
Anti-Inflammatory Agents, Non-Steroidal
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)
Protease Inhibitors
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)
Complement Inactivating Agents
Compounds that negatively regulate the cascade process of COMPLEMENT ACTIVATION. Uncontrolled complement activation and resulting cell lysis is potentially dangerous for the host. (See all compounds classified as Complement Inactivating Agents.)
Route of Elimination
Two metabolites of NM, p-guanidinobenzoic acid (PGBA) and 6-amidino-2-naphthol (AN), are renally excreted. Nafamostat accumulates in the kidneys.
Nafamostat is mainly hydrolyzed by hepatic carboxyesterase and long-chain acyl-CoA hydrolase in human liver cytosol. Main metabolites are p-guanidinobenzoic acid (PGBA) and 6-amidino-2-naphthol (AN) as inactive protease inhibitors.
Approximately 8 minutes
Nafamostat mesilate inhibits various enzyme systems, such as coagulation and fibrinolytic systems (thrombin, Xa, and XIIa), the kallikrein–kinin system, the complement system, pancreatic proteases and activation of protease-activated receptors (PARs). Nafamostat inhibits lipopolysaccharide-induced nitric oxide production, apoptosis, and interleukin (IL)-6 and IL-8 levels in cultured human trophoblasts. It is shown to act as an antioxidant in TNF-α-induced ROS production.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=MQQNFDZXWVTQEH-UHFFFAOYSA-N
Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
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- Drug Gene Interaction database (DGIdb)LICENSEThe data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.http://www.dgidb.org/downloadsNAFAMOSTAThttps://www.dgidb.org/drugs/ncit:C96292
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- Therapeutic Target Database (TTD)
- EU Clinical Trials Register
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- Japan Chemical Substance Dictionary (Nikkaji)
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- Metabolomics Workbench
- NIPH Clinical Trials Search of Japan
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- RCSB Protein Data Bank (RCSB PDB)LICENSEData files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.https://www.rcsb.org/pages/policies
- Springer Nature
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- Wikidatanafamostathttps://www.wikidata.org/wiki/Q15409374
- WikipediaNafamostathttps://en.wikipedia.org/wiki/Nafamostat
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlAnticoagulantshttps://www.ncbi.nlm.nih.gov/mesh/68000925Serine Proteinase Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68015842Trypsin Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68014361Anti-Inflammatory Agents, Non-Steroidalhttps://www.ncbi.nlm.nih.gov/mesh/68000894Protease Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68011480Complement Inactivating Agentshttps://www.ncbi.nlm.nih.gov/mesh/68051056
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 403518489https://pubchem.ncbi.nlm.nih.gov/substance/403518489
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