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Chemistry

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Also known as: Camostat mesilate, 59721-29-8, Camostat (mesylate), Camostat methanesulfonate, Foipan, Camostate

Molecular Formula

C₂₁H₂₆N₄O₈S

Molecular Weight

494.5 g/mol

InChI Key

FSEKIHNIDBATFG-UHFFFAOYSA-N

FDA UNII

451M50A1EQ

Camostat Mesylate is the mesylate salt form of camostat, an orally bioavailable, synthetic serine protease inhibitor, with anti-inflammatory, antifibrotic, and potential antiviral activities. Upon oral administration, camostat and its metabolite 4-(4-guanidinobenzoyloxyl)phenyl acetic acid (FOY 251) inhibit the activities of a variety of proteases, including trypsin, kallikrein, thrombin and plasmin, and C1r- and C1 esterases. Although the mechanism of action of camostat is not fully understood, trypsinogen activation in the pancreas is known to be a trigger reaction in the development of pancreatitis. Camostat blocks the activation of trypsinogen to trypsin and the inflammatory cascade that follows. Camostat may also suppress the expression of the cytokines interleukin-1beta (IL-1b), interleukin-6 (IL-6), tumor necrosis factor-alpha (TNF-a) and transforming growth factor-beta (TGF-beta), along with alpha-smooth muscle actin (alpha-SMA). This reduces inflammation and fibrosis of the pancreas. In addition, camostat 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

Camostat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-[2-[2-(dimethylamino)-2-oxoethoxy]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate;methanesulfonic acid

2.1.2 InChI

InChI=1S/C20H22N4O5.CH4O3S/c1-24(2)17(25)12-28-18(26)11-13-3-9-16(10-4-13)29-19(27)14-5-7-15(8-6-14)23-20(21)22;1-5(2,3)4/h3-10H,11-12H2,1-2H3,(H4,21,22,23);1H3,(H,2,3,4)

2.1.3 InChI Key

FSEKIHNIDBATFG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)C(=O)COC(=O)CC1=CC=C(C=C1)OC(=O)C2=CC=C(C=C2)N=C(N)N.CS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

451M50A1EQ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Camostat

2. Camostat Mesilate

3. Camostate

4. Camostate-mesilate

5. Foipan

6. Foy 305

7. Foy S 980

8. Foy-305

9. Foypan

10. N,n-dimethylcarbamoylmethyl-4-(4-guanidinobenzoyloxy)phenylacetate Methanesulfonate

11. P-guanidinobenzoic Acid, Ester With (p-hydroxyphenyl)acetic Acid, Ester With N,n-dimethylglycolamide

2.3.2 Depositor-Supplied Synonyms

1. Camostat Mesilate

2. 59721-29-8

3. Camostat (mesylate)

4. Camostat Methanesulfonate

5. Foipan

6. Camostate

7. Mfcd00941410

8. Foy305

9. Camostat Mesilate [jan]

10. Camostat Mesilate;foy305;foy-s980

11. Dsstox_cid_238

12. 4-(2-(2-(dimethylamino)-2-oxoethoxy)-2-oxoethyl)phenyl 4-guanidinobenzoate Methanesulfonate

13. Dsstox_rid_75452

14. Dsstox_gsid_20238

15. Chembl85164

16. 2-(dimethylamino)-2-oxoethyl 4-(4-guanidinobenzoyloxy)phenylacetate Methanesulphonate

17. Methanesulfonic Acid 4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate

18. 451m50a1eq

19. Cas-59721-29-8

20. Ncgc00167526-01

21. Foy-305

22. Foipan (tn)

23. Camostat Mesylate- Bio-x

24. Camostat Mesilate (jp17)

25. Mls006010697

26. Schembl871583

27. Foy-s980

28. Camostat Mesilate (foy-305)

29. Dtxsid0020238

30. Chebi:31347

31. Amy8832

32. Camostat Mesilate [mart.]

33. Hms3651d04

34. Camostat Mesilate [who-dd]

35. Bcp06708

36. Ex-a4154

37. Tox21_112523

38. Camostat Mesylate, >=98% (hplc)

39. S2874

40. Camostat Methanesulfonate [mi]

41. Akos015966692

42. Akos026750463

43. Tox21_112523_1

44. Ac-8540

45. Ccg-269652

46. Hs-0060

47. Ncgc00167526-02

48. 4-(2-(2-(dimethylamino)-2-oxoethoxy)-2-oxoethyl)phenyl 4-((diaminomethylene)amino)benzoate Methanesulfonate

49. 4-[[4-[(aminoiminomethyl)amino]benzoyl]oxy]benzeneacetic Acid 2-(dimethylamino)-2-oxoethyl Ester Methanesulfonate

50. Bc164270

51. Hy-13512

52. Smr002530343

53. Sy060177

54. Db-072684

55. B2082

56. Ft-0648873

57. Sw219517-1

58. D01766

59. F20649

60. 721c298

61. A832436

62. Q-200778

63. Q23731028

64. 4-(2-(2-(dimethylamino)-2-oxoethoxy)-2-oxoethyl)phenyl4-guanidinobenzoatemethanesulfonate

65. 4-(2-{[2-(dimethylamino)-2-oxoethyl]oxy}-2-oxoethyl)phenyl 4-{[amino(imino)methyl]amino}benzoate Methanesulfonate

66. 4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-[(diaminomethylidene)amino]benzoate; Methanesulfonic Acid

2.4 Create Date

2005-11-20

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₆N₄O₈S
Molecular Weight	494.5 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	9
Exact Mass	494.14713497 g/mol
Monoisotopic Mass	494.14713497 g/mol
Topological Polar Surface Area	200 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	695
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	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Trypsin Inhibitors

Serine proteinase inhibitors which inhibit trypsin. They may be endogenous or exogenous compounds. (See all compounds classified as Trypsin Inhibitors.)

Protease Inhibitors

Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)

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