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Details

Stereochemistry ACHIRAL
Molecular Formula C19H17N5O2
Molecular Weight 347.3706
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAFAMOSTAT

SMILES

NC(=N)NC1=CC=C(C=C1)C(=O)OC2=CC3=C(C=C2)C=C(C=C3)C(N)=N

InChI

InChIKey=MQQNFDZXWVTQEH-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Nafamostat mesilate (NM), a synthetic serine protease inhibitor, has anticoagulant and anti-inflammatory properties. Nafamostat is approved and marketed in Japan. It relieves symptoms such as pain due to inflammation of the spleen. It improves visceral disorders and bleeding tendency caused by blood clotting tendency in the vessels. It prevents coagulation in the blood circuit during hemodialysis. It is usually used to improve acute symptoms of pancreatitis (acute pancreatitis, acute exacerbation phase of chronic pancreatitis, post-operative acute pancreatitis, acute pancreatitis after pancreatography, traumatic pancreatitis) and to prevent disseminated intravascular coagulation (DIC) and clotting of perfusing blood in extracorporeal blood circuit. Nafamostat mesilate significantly inhibits the release of platelet beta-thromboglobulin (beta TG) at 60 and 120 min. Nafamostat mesilate (NM) prevents any significant release of neutrophil elastase; at 120 min, plasma elastase-alpha 1-antitrypsin complex is 0.16 mg/mL in the NM group and 1.24 mg/mL in the control group. Nafamostat mesilate completely inhibits formation of complexes of C1 inhibitor with kallikrein and FXIIa.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NAFAMOSTAT

Approved Use

This medicine relieves symptoms such as pain due to inflammation of the spleen. It improves visceral disorders and bleeding tendency caused by blood clotting tendency in the vessels. It prevents coagulation in the blood circuit during hemodialysis. It is usually used to improve acute symptoms of pancreatitis (acute pancreatitis, acute exacerbation phase of chronic pancreatitis, post-operative acute pancreatitis, acute pancreatitis after pancreatography, traumatic pancreatitis) and to prevent disseminated intravascular coagulation (DIC) and clotting of perfusing blood in extracorporeal blood circuit.
Preventing
NAFAMOSTAT

Approved Use

This medicine relieves symptoms such as pain due to inflammation of the spleen. It improves visceral disorders and bleeding tendency caused by blood clotting tendency in the vessels. It prevents coagulation in the blood circuit during hemodialysis. It is usually used to improve acute symptoms of pancreatitis (acute pancreatitis, acute exacerbation phase of chronic pancreatitis, post-operative acute pancreatitis, acute pancreatitis after pancreatography, traumatic pancreatitis) and to prevent disseminated intravascular coagulation (DIC) and clotting of perfusing blood in extracorporeal blood circuit.
PubMed

PubMed

TitleDatePubMed
Successful treatment of levodopa-induced neuroleptic malignant syndrome (NMS) and disseminated intravascular coagulation (DIC) in a patient with Parkinson's disease.
1992 Nov
Nafamostat mesilate, a kallikrein inhibitor, prevents pain on injection with propofol.
1998 Dec
A potential mechanism of propofol-induced pain on injection based on studies using nafamostat mesilate.
1999 Sep
Benefit of continuous regional arterial infusion of protease inhibitor and antibiotic in the management of acute necrotizing pancreatitis.
2001
[Anti-bleeding effect of nafamostat mesilate for the surgery of thoracic ascending aorta].
2001 Aug
Regional effects of nafamostat, a novel potent protease and complement inhibitor, on severe necrotizing pancreatitis.
2001 Aug
Attenuation of hepatic ischemia and reperfusion injury by serine protease inhibitor, FUT-175, in dogs.
2001 Feb-Mar
The efficacy of nafamostat mesilate on the performance of a hybrid-artificial liver using a polyurethane foam/porcine hepatocyte spheroid culture system in human plasma.
2001 Jan
Broad-spectrum and selective serine protease inhibitors prevent expression of platelet-derived growth factor-BB and cerebral vasospasm after subarachnoid hemorrhage: vasospasm caused by cisternal injection of recombinant platelet-derived growth factor-BB.
2001 Jul
Can nafamostat mesilate be used for temporary management of hemodialysis in a patient with heparin-induced thrombocytopenia (HIT)?
2001 Oct
Inhibition of natural killer cytotoxicity in vitro by clinical grade serine protease inhibitors.
2002
Nafamostat mesilate is an extremely potent inhibitor of human tryptase.
2003 Aug
Successful adult ABO-incompatible liver transplantation: therapeutic strategy for thrombotic microangiopathy is the key to success.
2003 May 15
Pharmacokinetics of nafamostat mesilate during continuous hemodiafiltration with a polyacrylonitrile membrane.
2003 Oct
Nafamostat mesilate suppresses NF-kappaB activation and NO overproduction in LPS-treated macrophages.
2003 Sep
[Fulminant myocarditis treated with percutaneous cardiopulmonary support and long-term complications: three case reports].
2004 Apr
A serine protease inhibitor, nafamostat mesilate, suppresses aldosterone secretions in vivo.
2004 Dec
Pancreatic enzymes in the gut contributing to lung injury after trauma/hemorrhagic shock.
2004 Feb
Transporter-mediated renal handling of nafamostat mesilate.
2004 Feb
Intraoperative management of a congenital antithrombin deficient patient on chronic hemodialysis.
2004 Jul
[Heparin-induced thrombocytopenia in patients on hemodialysis].
2004 Jun
[Treatment of uremic patients with high bleeding risk].
2004 Jun
[Blood purification for patients with chronic renal failure accompanied by severe liver disease].
2004 Jun
[Anticoagulant].
2004 May
Efficacy of continuous regional arterial infusion of a protease inhibitor and antibiotic for severe acute pancreatitis in patients admitted to an intensive care unit.
2004 May
[Treatment of acute pancreatitis with protease inhibitor, H2 receptor antagonist and somatostatin analogue].
2004 Nov
Continuous hemodiafiltration in pediatric critical care patients.
2004 Oct
[Role of pancreatic enzymes in gut injury secondary to trauma/hemorrhagic shock in rats].
2004 Oct
Nafamostat preserves neutrophil deformability and reduces microaggregate formation during simulated extracorporeal circulation.
2005 Apr
Correlation between serum nafamostat mesilate and activated coagulation time during continuous hemodiafiltration.
2005 Apr
Effect of intraportal infusion to improve small for size graft injury in living donor adult liver transplantation.
2005 Aug
[A patient with Vibrio vulnificus meningoencephalitis].
2005 Jan
Open heart surgery in a patient with paroxysmal nocturnal hemoglobinuria.
2005 Jun
Involvement of human blood arylesterases and liver microsomal carboxylesterases in nafamostat hydrolysis.
2006 Apr
Nafamostat attenuated the impairment of fibrinolysis in animal sepsis model by suppressing the increase of plasminogen activator inhibitor type 1.
2006 Apr
Anti-tryptase treatment using nafamostat mesilate has a therapeutic effect on experimental colitis.
2006 Aug
The role of a protease inhibitor against hepatectomy.
2006 Jan-Feb
Topical application of epidermal growth factor accelerates wound healing by myofibroblast proliferation and collagen synthesis in rat.
2006 Jun
Human complement-activating immunoglobulin (Ig)G3 antibodies are essential for porcine endothelial cell activation.
2006 May
Complement activation is involved in biological responses to leukocyte adsorptive apheresis.
2006 May
Properties of poly(lactic-co-glycolic acid) nanospheres containing protease inhibitors: camostat mesilate and nafamostat mesilate.
2006 May 11
Nafamostat mesilate inhibits high-mobility group box 1 by lipopolysaccharide stimulation in murine macrophage RAW 264.7.
2007 Apr
Pancreatic enzymes generate cytotoxic mediators in the intestine.
2007 Mar
Low-volume continuous hemodiafiltration with nafamostat mesilate increases trypsin clearance without decreasing plasma trypsin concentration in severe acute pancreatitis.
2007 Mar-Apr
Mechanisms of synthetic serine protease inhibitor (FUT-175)-mediated cell death.
2007 May 15
Patents

Sample Use Guides

Acute Kidney Injury: Initial dose of nafamostat mesilate is 20mg/hr. Dosage is adjusted from 10mg to 30mg/hr according to patients' status. For priming, two vial of nafamostat mesilate was dissolved in 2mL of 5% glucose fluid, and then mixed with 1000mL of normal saline. After carefully removing air bubble from the circuit with the prepared fluid, nafamostat mesilate was dissolved with 15 mL of 5% glucose fluid and loaded in anticoagulation line with starting dose of 20mg/hr.
Route of Administration: Intravenous
In Vitro Use Guide
Nafamostat inhibited extrinsic pathway activity (TF-F.VIIa mediated-F.Xa generation) in a concentration dependent manner; the IC50 was 1.0 x 10(-7) M. Nafamostat inhibited TF-F.VIIa complex activity with an IC50 of 1.5 x 10(-7) M.
Name Type Language
NAFAMOSTAT
INN   MI   WHO-DD  
INN  
Official Name English
Nafamostat [WHO-DD]
Common Name English
BENZOIC ACID, 4-((AMINOIMINOMETHYL)AMINO)-, 6-(AMINOIMINOMETHYL)-2-NAPHTHALENYL ESTER
Common Name English
nafamostat [INN]
Common Name English
NAFAMOSTAT [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 835721
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
NCI_THESAURUS C783
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
NCI_THESAURUS C257
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
FDA ORPHAN DRUG 742120
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL273264
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID0048420
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
PUBCHEM
4413
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
DRUG BANK
DB12598
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
EVMPD
SUB09114MIG
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
SMS_ID
100000091465
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
FDA UNII
Y25LQ0H97D
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
CAS
81525-10-2
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
DRUG CENTRAL
1867
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
MERCK INDEX
M7704
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
NAFAMOSTAT
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
IUPHAR
4262
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
INN
5682
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
MESH
C032855
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY
NCI_THESAURUS
C96292
Created by admin on Wed Jul 05 23:20:26 UTC 2023 , Edited by admin on Wed Jul 05 23:20:26 UTC 2023
PRIMARY