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Nafamostat

Synopsis, Chemistry

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Also known as: 81525-10-2, Nafamostat [inn], Nafamstat, (6-carbamimidoylnaphthalen-2-yl) 4-(diaminomethylideneamino)benzoate, Chembl273264, Y25lq0h97d

Molecular Formula

C₁₉H₁₇N₅O₂

Molecular Weight

347.4 g/mol

InChI Key

MQQNFDZXWVTQEH-UHFFFAOYSA-N

FDA UNII

Y25LQ0H97D

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.

1 2D Structure

Nafamostat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6-carbamimidoylnaphthalen-2-yl) 4-(diaminomethylideneamino)benzoate

2.1.2 InChI

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)

2.1.3 InChI Key

MQQNFDZXWVTQEH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC=C1C(=O)OC2=CC3=C(C=C2)C=C(C=C3)C(=N)N)N=C(N)N

2.2 Other Identifiers

2.2.1 UNII

Y25LQ0H97D

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6'-amidino-2-naphthyl 4-guanidinobenzoate

2. 6'-amidino-2-naphthyl 4-guanidinobenzoate, Dimethanesulfonate

3. Benzoic Acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl Ester

4. Benzoic Acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl Ester, Dihydrochloride

5. Benzoic Acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl Ester, Dimethanesulfonate

6. Ckd-314

7. Ckd314

8. Fut 175

9. Fut-175

10. Nafamostat Dihydrochloride

11. Nafamostat Mesilate

12. Nafamostat Mesylate

13. Nafamstat Mesilate

14. Ronastat

2.3.2 Depositor-Supplied Synonyms

1. 81525-10-2

2. Nafamostat [inn]

3. Nafamstat

4. (6-carbamimidoylnaphthalen-2-yl) 4-(diaminomethylideneamino)benzoate

5. Chembl273264

6. Y25lq0h97d

7. P-guanidinobenzoic Acid Ester With 6-hydroxy-2-naphthamidine

8. Nafamostat (inn)

9. Benzoic Acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl Ester

10. 6-carbamimidoylnaphthalen-2-yl 4-guanidinobenzoate

11. Nafamostatum [latin]

12. Nafamostatum

13. Nafamostat Mesylate(fut-175)

14. 6-[amino(imino)methyl]-2-naphthyl 4-{[amino(imino)methyl]amino}benzoate Dimethanesulfonate

15. Ncgc00160398-01

16. 6-amidino2-naphthyl 4-guanidinobenzoate

17. Unii-y25lq0h97d

18. Nafabelltan

19. Ckd314

20. Ckd-314

21. Nafamostat [mi]

22. 6-(aminoiminomethyl)-2-naphthalenyl 4-((aminoiminomethyl)amino)benzoate

23. Nafamostat [who-dd]

24. Bspbio_001194

25. Schembl135503

26. Gtpl4262

27. Dtxsid0048420

28. Amy8858

29. Chebi:135466

30. Hms3742k19

31. Albb-027243

32. Bcp13085

33. Hy-b0190

34. Zinc3874467

35. Bdbm50063698

36. Akos017259237

37. Db12598

38. 6-amidino-2-naphthyl P-guanidinobenzoate

39. Ncgc00160398-02

40. Ncgc00160398-03

41. Ncgc00160398-04

42. Ncgc00160398-13

43. Bs-17665

44. B1177

45. Ft-0629861

46. Fut-175; Fut 175; Fut175

47. D08240

48. Mls-0435512.0001

49. Ab01566816_01

50. 525n102

51. A840154

52. Q15409374

53. (6-carbamimidoyl-2-naphthyl) 4-guanidinobenzoate;nafamostat

54. (6-carbamimidoylnaphthalen-2-yl) 4-carbamimidamidobenzoate

55. 4-guanidino-benzoic Acid 6-carbamimidoyl-naphthalen-2-yl Ester

56. 6-carbamimidoylnaphthalen-2-yl 4-[(diaminomethylidene)amino]benzoate

57. 4-guanidino-benzoic Acid 6-carbamimidoyl-naphthalen-2-yl Ester(fut-175)

58. Benzoic Acid, 4-[(aminoiminomethyl)amino]-,6-(aminoiminomethyl)-2-naphthalenyl Ester

59. Benzoic Acid, 4-[(aminoiminomethyl)amino]-, 6-(aminoiminomethyl)-2-naphthalenyl Ester, Methanesulfonate (1:2)

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₇N₅O₂
Molecular Weight	347.4 g/mol
XLogP3	2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	347.13822480 g/mol
Monoisotopic Mass	347.13822480 g/mol
Topological Polar Surface Area	141 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	552
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

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.

5 Pharmacology and Biochemistry

5.1 Pharmacology

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.

5.2 MeSH Pharmacological Classification

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.)

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.)

5.3 Absorption, Distribution and Excretion

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.

5.4 Metabolism/Metabolites

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.

5.5 Biological Half-Life

Approximately 8 minutes

5.6 Mechanism of Action

Nafamostat mesilate inhibits various enzyme systems, such as coagulation and fibrinolytic systems (thrombin, Xa, and XIIa), the kallikreinkinin 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--induced ROS production.