6-carbamimidoylnaphthalen-2-yl 4-[(diaminomethylidene)amino]benzoate
Nafamostat
CAS: 81525-10-2
Molecular Formula: C19H17N5O2
6-carbamimidoylnaphthalen-2-yl 4-[(diaminomethylidene)amino]benzoate - Names and Identifiers
| Name | Nafamostat |
| Synonyms | FUTHAN FUT-175 Nafamstat Nafamostat Nafamostatum Nafamostat [INN] NAFAMOSTAT MESILATE Nafamostatum [Latin] NafamostatMesilateBase Nafamostat Dimethanesulfonate 6-Amidino2-naphthyl 4-guanidinobenzoate 6-Amidino-2-naphthyl 4-guanidinobenzoate 6-AMIDINO-2-NAPHTHYL-4-GUANIDINOENZOATE, MESYLATE p-Guanidinobenzoic acid ester with 6-hydroxy-2-naphthamidine 6-carbamimidoylnaphthalen-2-yl 4-[(diaminomethylidene)amino]benzoate 6-(Aminoiminomethyl)-2-naphthalenyl 4-((aminoiminomethyl)amino)benzoate Benzoic acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl ester |
| CAS | 81525-10-2 |
| EINECS | 1806241-263-5 |
| InChI | InChI=1/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) |
6-carbamimidoylnaphthalen-2-yl 4-[(diaminomethylidene)amino]benzoate - Physico-chemical Properties
| Molecular Formula | C19H17N5O2 |
| Molar Mass | 347.37 |
| Density | 1.39±0.1 g/cm3(Predicted) |
| Boling Point | 586.0±60.0 °C(Predicted) |
| Flash Point | 339.1°C |
| Vapor Presure | 3.9E-16mmHg at 25°C |
| pKa | 11.30±0.30(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2–8 °C |
| Refractive Index | 1.694 |
| Physical and Chemical Properties | Nafamostat Mesylate: C19H17N5O2? 2CH3SO3H. [82956-11-4]. Crystallization from ether, melting point 217~220 ℃; Or colorless powder from water, melting point 260 ℃ (decomposition). Odorless and bitter. Soluble in water, difficult to dissolve in methanol, ethanol or dimethyl formamide, a few do not dissolve in ether, chloroform or acetone. Acute toxicity LD50 male and female mice, male and female rats (mg/kg):4600,5190,3050,2750 oral; 6180,55650,9200,9750 subcutaneous injection; 269,350,162,150 intraperitoneal injection; 24.4,31.1,16.4,17.0 intravenous injection. |
6-carbamimidoylnaphthalen-2-yl 4-[(diaminomethylidene)amino]benzoate - Reference Information
| Overview | nemostat is a synthetic serine proteolytic enzyme inhibitor for trypsin, kallikrein (vasopressin), plasmin, protease and complement system related enzymes have a strong selective inhibitory effect on phospholipase A2, in vitro and Alpha 2 macroglobulin binding trypsin also has inhibitory effect; With anticoagulant, anti-fibrinolytic enzyme and anti-platelet aggregation and other pharmacological effects; In addition to acute exacerbation of chronic pancreatitis, as well as acute pancreatitis of various causes, improvement of acute symptoms of pancreatitis, also used for hemodialysis, coronary artery bypass grafting, anticoagulation at the time of liver resection, and glomerulonephritis with systemic lupus erythematosus or mixed cryoglobulinemia. |
| preparation method | reaction of 6-bromo-2-naphthol and copper cyanide in dimethylformamide, 6-cyano -2-naphthol is produced, and then amolyzed after methanol solution, to produce 6-amidino-2-naphthol, and finally esterification with guanidylbenzoic acid, that is, the generation of the naphthalene. The crude nemostat can be recrystallized with water. |
| pharmacological effects | this drug is a synthetic serine proteolytic enzyme inhibitor, with anticoagulant, antiplasmin and anti-platelet aggregation. Specific features are as follows: 1. Enzyme Inhibition: CL-r of the classic pathway of the trypsin, kallikrein (vasopressin), plasmin, fiber protease and the complement system, CL-s and other trypsin like serine protease has a strong selective inhibitory effect on phospholipase A2. Trypsin binding to α2-macroglobulin was also inhibited in vitro. 2. The role of experimental acute pancreatitis: rats and rabbits intravenous infusion of the drug, trypsin, intestinal kinase and endotoxin via the pancreatic duct retrograde injection caused by a variety of experimental pancreatitis, it can inhibit the increase of pancreatic enzyme activity caused by pancreatitis and the activity of the enzyme entering the blood, and decrease by Mortality Rate. 3. Effect on kallikrein-Kinin system: the administration of this drug to patients with pancreatitis can improve the reduction of the total amount of kininogen caused by the activation of kallikrein. 4. Effect on blood coagulation and fibrinolysis system: nemostat produces anticoagulant effect by inhibiting fibrin and coagulation factors ΔA and Xa. In vitro experiments also found that the drug can inhibit platelet aggregation. In animal experiments, the intravenous administration of the present drug can prolong the activated partial thromboplastin (thromboplastin) time and urokinase-activated fibrinolysis time in rabbits. Since Heparin increases the risk of bleeding, the drug can be used as an alternative to heparin. 5. Effect on Complement system: oral administration and intravenous injection of the drug can prolong the life of the guinea pig with systemic Forsmann heterophile Shock caused by intravenous injection of hemolysin. |
| pharmacokinetics | healthy men were given 10mg, 20mg and 40mg of the drug by intravenous drip within 90min, the peak plasma concentrations were 16.4ng/ml, 61.5ng/ml and 93.2ng/ml, respectively, within 60-90min. The distribution of drug concentration in the tissues from high to low were kidney, liver, lung and pancreas, which were higher than the blood concentration. The drug was rapidly cleared from the blood, and the blood concentration decreased to less than 5ng/ml 1h after stopping the drug, and was only detectable from the liver 4h after administration. The drug is mainly metabolized in the blood and liver, excreted by the kidneys. |
| Use | 1. For acute exacerbation of chronic pancreatitis, as well as acute pancreatitis caused by various reasons, the improvement of acute symptoms of pancreatitis. 2. For hemodialysis, coronary artery bypass grafting, liver resection of anticoagulation, and glomerulonephritis with systemic lupus erythematosus or mixed cryoglobulinemia (cryoglobulinemia). (2015-11-2) non-peptide synthetic protease inhibitors, with a broad spectrum of potent enzyme inhibition. For the treatment of acute pancreatitis. It can improve acute symptoms of acute pancreatitis, acute exacerbation of chronic pancreatitis, post-traumatic pancreatitis, and the like. |
| adverse reactions | 1. Allergic reactions: rash, erythema, pruritus (1.7%). 2. Digestive system: Nausea, Diarrhea (0.3%) and other gastrointestinal reactions, can also appear alanine aminotransferase, aspartate aminotransferase increased (0.5%). 3. Blood: leukopenia and increased platelets. 4. Local: redness, swelling and pain at injection site were rare. 5 Other: chest discomfort, Head Pain, etc. |
| note | 1. The powder for injection should be used immediately after dissolution. Rash, erythema, itching and other allergic symptoms should be discontinued. Shock symptoms should be immediately discontinued. 2. With caution:(1) allergies. (2) have a history of allergy. (3) active bleeding (due to continuous infusion of the drug and increase the risk of bleeding). (4) patients with severe hypertension (increased risk of cerebral hemorrhage) (foreign data). (5) patients with severe thrombocytopenia (increased risk of bleeding) (foreign data). (6) hyperkalemia (the use of this drug may aggravate hyperkalemia) patients (foreign data). (7) children. 3. The effect of drugs on pregnancy: Pregnant women should use this drug with caution. 4. The impact of the drug on lactation: Lactating women with caution in the use of this drug. 5. Before and after medication and medication should be checked or monitored: should be regularly monitored:(1) blood routine, platelet count and serum potassium. (2) activated partial thromboplastin time (APTT), activated whole blood coagulation time (ACT), coagulation factor II time (PT), thrombin-antithrombin complex (TAT), α2 plasmin inhibitor-plasmin complex (PIC), coagulation factor I and fibrin degradation products (FDP). |
| production method | the reaction of 6-bromo-2-naphthol and copper cyanide in dimethylformamide, 6-cyano -2-naphthol is produced, and then amolyzed after methanol solution, to produce 6-amidino-2-naphthol, and finally esterification with guanidylbenzoic acid, that is, the generation of the naphthalene. The crude nemostat can be recrystallized with water. |
Last Update：2024-04-09 21:04:16
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CAS: 81525-10-2
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Mobile: 18021002903
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