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    Camostatum

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 59721-28-7, Camostat [inn], Camostate, [4-[2-[2-(dimethylamino)-2-oxoethoxy]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate, 0fd207wkdu, 4-(2-(2-(dimethylamino)-2-oxoethoxy)-2-oxoethyl)phenyl 4-guanidinobenzoate
    Molecular Formula
    C20H22N4O5
    Molecular Weight
    398.4  g/mol
    InChI Key
    XASIMHXSUQUHLV-UHFFFAOYSA-N
    FDA UNII
    0FD207WKDU
    Camostat is 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
    2.1.2 InChI
    InChI=1S/C20H22N4O5/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/h3-10H,11-12H2,1-2H3,(H4,21,22,23)
    2.1.3 InChI Key
    XASIMHXSUQUHLV-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
    2.2 Other Identifiers
    2.2.1 UNII
    0FD207WKDU
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Camostat Mesilate

    2. Camostat Mesylate

    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. 59721-28-7

    2. Camostat [inn]

    3. Camostate

    4. [4-[2-[2-(dimethylamino)-2-oxoethoxy]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate

    5. 0fd207wkdu

    6. 4-(2-(2-(dimethylamino)-2-oxoethoxy)-2-oxoethyl)phenyl 4-guanidinobenzoate

    7. Camostat (inn)

    8. Foipan

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

    10. Camostatum

    11. Camostatum [inn-latin]

    12. Chembl85164

    13. Ccris 7219

    14. Ncgc00167526-01

    15. Unii-0fd207wkdu

    16. Camostat-mesilate

    17. Dimethylcarbamoylmethyl 4-(4-guqnidinobenzoyloxy)phenylacetat

    18. Camostat [mi]

    19. Camostat [who-dd]

    20. Us9199927, Camostat

    21. Schembl125269

    22. Chembl590799

    23. Gtpl6432

    24. Dtxsid6044010

    25. Chebi:135632

    26. Bdbm193418

    27. Bcp22042

    28. Ex-a5738

    29. Zinc3871842

    30. Bdbm50031706

    31. Bdbm50424712

    32. Bcp9000475

    33. Db13729

    34. Ncgc00167526-03

    35. Db-053447

    36. Ft-0630715

    37. D07606

    38. 721c287

    39. Q5026909

    40. 2-(dimethylamino)-2-oxoethyl4-(4-guanidinobenzoyloxy)phenylacetate

    41. 4-(2-(2-(dimethylamino)-2-oxoethoxy)-2-oxoethyl)phenyl4-guanidinobenzoate

    42. N,n-dimethyl Carbamoylmethyl-p-(p-guanidinobenzoyloxy) Phenyl-acetate

    43. [4-[2-(2-dimethylamino-2-oxoethoxy)-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate

    44. 4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate

    45. 4-guanidino-benzoic Acid 4-dimethylcarbamoylmethoxycarbonylmethyl-phenyl Ester; Compound With Methanesulfonic Acid

    46. Benzeneacetic Acid,4-((4-((aminoiminomethyl)amino)benzoyl)oxy)-,2-(dimethylamino)-2-oxoethyl Ester

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 398.4 g/mol
    Molecular Formula C20H22N4O5
    XLogP31.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count9
    Exact Mass398.15901982 g/mol
    Monoisotopic Mass398.15901982 g/mol
    Topological Polar Surface Area137 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity602
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Camostat mesylate is indicated in Japan to treat chronic pancreatitis and drug induced lung injury. It is also being investigated as a potential treatment for COVID-19.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Camostat mesylate is a protease inhibitor used to treat chronic pancreatitis. The duration of action is not long, as it is typically given in 3 divided doses daily. Patients should be counselled regarding the risk of anaphylaxis, thrombocytopenia, hepatic dysfunction, and hyperkalemia.

    5.2 MeSH Pharmacological Classification

    Protease Inhibitors

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

    Trypsin Inhibitors

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

    5.3 ATC Code

    B - Blood and blood forming organs

    B02 - Antihemorrhagics

    B02A - Antifibrinolytics

    B02AB - Proteinase inhibitors

    B02AB04 - Camostat

    5.4 Absorption, Distribution and Excretion

    Absorption

    A 200mg oral dose of camostat mesylate leads to the active metabolite reaching a Cmax of 87.1 29.5 ng/mL, with a Tmax of 40 min, and an AUC of 10,400 1,400 ng\*min/mL.

    Route of Elimination

    Camostat mesylate is 89.8-95.6% eliminated in the urine and 1.0-1.7% eliminated in the feces.

    Volume of Distribution

    The volume of distribution at steady state of camostat mesylate is 0.34-1.31L/kg.

    Clearance

    The clearance of camostat mesylate is 4.5-7.3mL/min/kg.

    5.5 Metabolism/Metabolites

    Camostat mesylate is hydrolyzed by carboxyesterate to the active 4-(4-guanidinobenzoyloxy) phenylacetate. The active metabolite is further hydrolyzed by arylesterase to 4-guanidinobenzoic acid.

    5.6 Biological Half-Life

    The half life of camostat mesylate is 3.8-4.7h.

    5.7 Mechanism of Action

    In rats, oral camostat mesylate may increase pancreatic secretions and hypertrophy by increasing cholecystokinin release. Administration in rats has also lead to lower levels of IL-1beta, IL-6, TNF-alpha, TGF-beta, and PSC. Similar activity is seem after administration in humans, leading to reduced pain and inflammation as well as improve the function of the pancrease in chronic pancreatitis. In the case of SARS-CoV-2, camostat mesylate inhibits the action of the serine protease TMPRSS2, preventing the priming of the viral spike protein for attachment to ACE2, and entry into the cell.