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    Camostat

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    2D Structure
    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

    2D Structure

    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 Weight 494.5 g/mol
    Molecular Formula C21H26N4O8S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count9
    Exact Mass494.14713497 g/mol
    Monoisotopic Mass494.14713497 g/mol
    Topological Polar Surface Area200 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity695
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    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.)