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Camostatum

Camostatum

Synopsis, Chemistry

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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

Camostatum

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 Formula	C₂₀H₂₂N₄O₅
Molecular Weight	398.4 g/mol
XLogP3	1.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	9
Exact Mass	398.15901982 g/mol
Monoisotopic Mass	398.15901982 g/mol
Topological Polar Surface Area	137 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	602
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

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 C_max of 87.1 29.5 ng/mL, with a T_max 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.