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
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)
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL209 |
17.0 nM [IC50] | ||
Target ID: CHEMBL4611 |
12.0 µM [IC50] | ||
Target ID: CHEMBL2617 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12939527 |
95.3 pM [Ki] | ||
Target ID: CHEMBL1250412 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21122141 |
617.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | NAFAMOSTAT Approved UseThis 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. |
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Preventing | NAFAMOSTAT Approved UseThis 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
Title | Date | PubMed |
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[Fulminant myocarditis treated with percutaneous cardiopulmonary support and long-term complications: three case reports]. | 2004 Apr |
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A serine protease inhibitor, nafamostat mesilate, suppresses aldosterone secretions in vivo. | 2004 Dec |
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A case of heparin-induced thrombocytopenia with sepsis and congestive heart failure--first autopsy report on Japan--. | 2004 Dec |
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Detection of specific IgE antibodies to nafamostat mesilate as an indication of possible adverse effects of leukocytapheresis using nafamostat mesilate as anticoagulant. | 2004 Feb |
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Intraoperative management of a congenital antithrombin deficient patient on chronic hemodialysis. | 2004 Jul |
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[Pregnancy and delivery in patients with hemodialysis]. | 2004 Jun |
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[Heparin-induced thrombocytopenia in patients on hemodialysis]. | 2004 Jun |
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[Treatment of uremic patients with high bleeding risk]. | 2004 Jun |
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[Blood purification for patients with chronic renal failure accompanied by severe liver disease]. | 2004 Jun |
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Inhibition of enteral enzymes by enteroclysis with nafamostat mesilate reduces neutrophil activation and transfusion requirements after hemorrhagic shock. | 2004 Mar |
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[Anticoagulant]. | 2004 May |
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[Anticoagulation for plasmapheresis]. | 2004 May |
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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 |
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Effects of anti-inflammatory cytokine agent (FR167653) and serine protease inhibitor on warm ischemia-reperfusion injury of the liver graft. | 2004 May 27 |
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[Continuous regional arterial infusion of protease inhibitor and antibiotic for severe acute pancreatitis]. | 2004 Nov |
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[Treatment of acute pancreatitis with protease inhibitor, H2 receptor antagonist and somatostatin analogue]. | 2004 Nov |
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Pancreatic proteases and inflammatory mediators in peritoneal fluid during splanchnic arterial occlusion and reperfusion. | 2004 Nov |
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Continuous hemodiafiltration in pediatric critical care patients. | 2004 Oct |
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[Role of pancreatic enzymes in gut injury secondary to trauma/hemorrhagic shock in rats]. | 2004 Oct |
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Advanced glycation end products induce secretion of chemokines and apoptosis in human first trimester trophoblasts. | 2004 Sep |
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Nafamostat preserves neutrophil deformability and reduces microaggregate formation during simulated extracorporeal circulation. | 2005 Apr |
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Correlation between serum nafamostat mesilate and activated coagulation time during continuous hemodiafiltration. | 2005 Apr |
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Rat experimental model of continuous regional arterial infusion of protease inhibitor and its effects on severe acute pancreatitis. | 2005 Apr |
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Small volume resuscitation with hypertonic saline is more effective in ameliorating trauma-hemorrhagic shock-induced lung injury, neutrophil activation and red blood cell dysfunction than pancreatitic protease inhibition. | 2005 Aug |
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Mast cell tryptase stimulates DLD-1 carcinoma through prostaglandin- and MAP kinase-dependent manners. | 2005 Aug |
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Nafamostat mesilate induces production of interleukin-12 and -18 in human peripheral blood mononuclear cells. | 2005 Aug |
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Effect of intraportal infusion to improve small for size graft injury in living donor adult liver transplantation. | 2005 Aug |
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[A patient with Vibrio vulnificus meningoencephalitis]. | 2005 Jan |
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Physiology and pathophysiology of proteinase-activated receptors (PARs): role of tryptase/PAR-2 in vascular endothelial barrier function. | 2005 Jan |
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Open heart surgery in a patient with paroxysmal nocturnal hemoglobinuria. | 2005 Jun |
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Involvement of neutrophil recruitment and protease-activated receptor 2 activation in the induction of IL-18 in mice. | 2005 Nov |
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JPN Guidelines for the management of acute pancreatitis: medical management of acute pancreatitis. | 2006 |
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Nafamostat attenuated the impairment of fibrinolysis in animal sepsis model by suppressing the increase of plasminogen activator inhibitor type 1. | 2006 Apr |
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Implantation Serine Proteinases heterodimerize and are critical in hatching and implantation. | 2006 Dec 11 |
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Leukocytapheresis for ulcerative colitis: a comparative study of anticoagulant (nafamostat mesilate vs. dalteparin sodium) for reducing clinical complications. | 2006 Feb |
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[Quality of life in surgical treatment of pancreatic cancer]. | 2006 Jan |
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Myeloperoxidase as a marker of hemodialysis biocompatibility and oxidative stress: the underestimated modifying effects of heparin. | 2006 Jan |
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Potent pruritogenic action of tryptase mediated by PAR-2 receptor and its involvement in anti-pruritic effect of nafamostat mesilate in mice. | 2006 Jan 13 |
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The role of a protease inhibitor against hepatectomy. | 2006 Jan-Feb |
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Topical application of epidermal growth factor accelerates wound healing by myofibroblast proliferation and collagen synthesis in rat. | 2006 Jun |
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[Postoperative acute pulmonary thromboembolism treated with nafamostat mesilate]. | 2006 May |
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Complement activation is involved in biological responses to leukocyte adsorptive apheresis. | 2006 May |
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Properties of poly(lactic-co-glycolic acid) nanospheres containing protease inhibitors: camostat mesilate and nafamostat mesilate. | 2006 May 11 |
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Effects of nafamostat mesilate on ADP-induced platelet aggregation and disaggregation in hemodialysis patients. | 2006 May-Jun |
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Nafamostat mesilate inhibits high-mobility group box 1 by lipopolysaccharide stimulation in murine macrophage RAW 264.7. | 2007 Apr |
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Antitumor effects of Nafamostat mesilate on head and neck squamous cell carcinoma. | 2007 Dec |
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[Anticoagulation of extracorporeal circuit in critically ill patients]. | 2007 Jan-Feb |
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Pancreatic enzymes generate cytotoxic mediators in the intestine. | 2007 Mar |
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Low-volume continuous hemodiafiltration with nafamostat mesilate increases trypsin clearance without decreasing plasma trypsin concentration in severe acute pancreatitis. | 2007 Mar-Apr |
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Mechanisms of synthetic serine protease inhibitor (FUT-175)-mediated cell death. | 2007 May 15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01761994
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8029816
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.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
835721
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NCI_THESAURUS |
C783
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NCI_THESAURUS |
C257
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FDA ORPHAN DRUG |
742120
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Code System | Code | Type | Description | ||
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CHEMBL273264
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DTXSID0048420
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4413
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DB12598
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SUB09114MIG
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100000091465
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Y25LQ0H97D
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81525-10-2
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1867
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m7704
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PRIMARY | Merck Index | ||
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NAFAMOSTAT
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4262
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PRIMARY | |||
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5682
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PRIMARY | |||
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C032855
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PRIMARY | |||
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C96292
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)