Camostat
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Overview
- Description
- A medication used in Japan to treat a condition of the pancreas.
- Description
- A medication used in Japan to treat a condition of the pancreas.
- DrugBank ID
- DB13729
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 4
- Phase 2
- 17
- Phase 3
- 5
- Phase 4
- 1
Identification
- Summary
Camostat is a serine protease indicated in Japan to treat chronic pancreatitis.
- Generic Name
- Camostat
- DrugBank Accession Number
- DB13729
- Background
Camostat mesylate, or FOY-305, is a synthetic serine protease inhibitor.2,4 It was first described in the literature in 1981, as part of research on the inhibition of skin tumors in mice.8 Camostat mesylate inhibits cholecystokinin, pro-inflammatory cytokines, and serine proteases, leading to it being investigated for multiple indications including the treatment of COVID-19.6,7,1
Camostat mesylate was first approved in Japan in January 2006.9
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 398.4125
Monoisotopic: 398.159019834 - Chemical Formula
- C20H22N4O5
- Synonyms
- Camostat
- Camostatum
Pharmacology
- Indication
Camostat mesylate is indicated in Japan to treat chronic pancreatitis and drug induced lung injury.3 It is also being investigated as a potential treatment for COVID-19.1
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- Pharmacodynamics
Camostat mesylate is a protease inhibitor used to treat chronic pancreatitis.3 The duration of action is not long, as it is typically given in 3 divided doses daily.9 Patients should be counselled regarding the risk of anaphylaxis, thrombocytopenia, hepatic dysfunction, and hyperkalemia.9
- Mechanism of action
In rats, oral camostat mesylate may increase pancreatic secretions and hypertrophy by increasing cholecystokinin release.6 Administration in rats has also lead to lower levels of IL-1beta, IL-6, TNF-alpha, TGF-beta, and PSC.7 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.9
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.1
Target Actions Organism USerine protease 1 inhibitorHumans UTransmembrane protease serine 2 inhibitorHumans USuppressor of tumorigenicity 14 protein inhibitorHumans UCholecystokinin inhibitorHumans - 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.9
- Volume of distribution
The volume of distribution at steady state of camostat mesylate is 0.34-1.31L/kg.2
- Protein binding
Camostat mesylate is 25.8-28.2% protein bound to human serum proteins in vitro.9
- Metabolism
Camostat mesylate is hydrolyzed by carboxyesterate to the active 4-(4-guanidinobenzoyloxy) phenylacetate.2,9 The active metabolite is further hydrolyzed by arylesterase to 4-guanidinobenzoic acid.2,9
Hover over products below to view reaction partners
- Route of elimination
Camostat mesylate is 89.8-95.6% eliminated in the urine and 1.0-1.7% eliminated in the feces.2
- Half-life
The half life of camostat mesylate is 3.8-4.7h.2
- Clearance
The clearance of camostat mesylate is 4.5-7.3mL/min/kg.2
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Data regarding overdoses of camostat mesylate are not readily available, however common adverse effects include rash, pruritus, nausea, abnormal laboratory test values, and diarrhea.9
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAlbutrepenonacog alfa Camostat may increase the thrombogenic activities of Albutrepenonacog alfa. Alpha-1-proteinase inhibitor Alpha-1-proteinase inhibitor may increase the thrombogenic activities of Camostat. Alteplase The therapeutic efficacy of Camostat can be decreased when used in combination with Alteplase. Aminocaproic acid Aminocaproic acid may increase the thrombogenic activities of Camostat. Andexanet alfa Camostat may increase the thrombogenic activities of Andexanet alfa. - Food Interactions
- Take with food. Take after a meal.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Camostat mesilate 451M50A1EQ 59721-29-8 FSEKIHNIDBATFG-UHFFFAOYSA-N
Categories
- ATC Codes
- B02AB04 — Camostat
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Depsides and depsidones
- Sub Class
- Not Available
- Direct Parent
- Depsides and depsidones
- Alternative Parents
- Guanidinobenzoic acids and derivatives / Phenol esters / Benzoic acid esters / Phenoxy compounds / Benzoyl derivatives / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Guanidines / Carboxylic acid esters / Propargyl-type 1,3-dipolar organic compounds show 4 more
- Substituents
- Aromatic homomonocyclic compound / Benzenoid / Benzoate ester / Benzoic acid or derivatives / Benzoyl / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Carboxylic acid ester / Depside backbone show 16 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans
Chemical Identifiers
- UNII
- 0FD207WKDU
- CAS number
- 59721-28-7
- InChI Key
- XASIMHXSUQUHLV-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate
- SMILES
- CN(C)C(=O)COC(=O)CC1=CC=C(OC(=O)C2=CC=C(NC(N)=N)C=C2)C=C1
References
- General References
- Hoffmann M, Kleine-Weber H, Schroeder S, Kruger N, Herrler T, Erichsen S, Schiergens TS, Herrler G, Wu NH, Nitsche A, Muller MA, Drosten C, Pohlmann S: SARS-CoV-2 Cell Entry Depends on ACE2 and TMPRSS2 and Is Blocked by a Clinically Proven Protease Inhibitor. Cell. 2020 Apr 16;181(2):271-280.e8. doi: 10.1016/j.cell.2020.02.052. Epub 2020 Mar 5. [Article]
- Midgley I, Hood AJ, Proctor P, Chasseaud LF, Irons SR, Cheng KN, Brindley CJ, Bonn R: Metabolic fate of 14C-camostat mesylate in man, rat and dog after intravenous administration. Xenobiotica. 1994 Jan;24(1):79-92. doi: 10.3109/00498259409043223. [Article]
- Ota S, Hara Y, Kanoh S, Shinoda M, Kawano S, Fujikura Y, Kawana A, Shinkai M: Acute eosinophilic pneumonia caused by camostat mesilate: The first case report. Respir Med Case Rep. 2016 Jun 16;19:21-3. doi: 10.1016/j.rmcr.2016.06.005. eCollection 2016. [Article]
- Kitamura K, Tomita K: Proteolytic activation of the epithelial sodium channel and therapeutic application of a serine protease inhibitor for the treatment of salt-sensitive hypertension. Clin Exp Nephrol. 2012 Feb;16(1):44-8. doi: 10.1007/s10157-011-0506-1. Epub 2011 Nov 1. [Article]
- Tamura Y, Hirado M, Okamura K, Minato Y, Fujii S: Synthetic inhibitors of trypsin, plasmin, kallikrein, thrombin, C1r-, and C1 esterase. Biochim Biophys Acta. 1977 Oct 13;484(2):417-22. [Article]
- Goke B, Printz H, Koop I, Rausch U, Richter G, Arnold R, Adler G: Endogenous CCK release and pancreatic growth in rats after feeding a proteinase inhibitor (camostate). Pancreas. 1986;1(6):509-15. doi: 10.1097/00006676-198611000-00008. [Article]
- Jia D, Taguchi M, Otsuki M: Synthetic protease inhibitor camostat prevents and reverses dyslipidemia, insulin secretory defects, and histological abnormalities of the pancreas in genetically obese and diabetic rats. Metabolism. 2005 May;54(5):619-27. doi: 10.1016/j.metabol.2004.12.005. [Article]
- Ohkoshi M: Inhibition of growth of 3-methylcholanthrene-induced mouse skin tumor by protease inhibitor [N,N-dimethylcarbamoylmethyl 4-(4-guanidinobenzoyloxy)-phenylacetate] methanesulfate. Gan. 1981 Dec;72(6):959-64. [Article]
- Ono Pharmaceutical: Foipan Camostat Mesilate Oral Tablets [Link]
- External Links
- ChemSpider
- 2440
- BindingDB
- 50424712
- ChEBI
- 135632
- ChEMBL
- CHEMBL590799
- ZINC
- ZINC000003871842
- Wikipedia
- Camostat
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Withdrawn Treatment Coronavirus Disease 2019 (COVID‑19) / COVID 1 somestatus stop reason just information to hide 3 Completed Treatment Coronavirus Disease 2019 (COVID‑19) 1 somestatus stop reason just information to hide 3 Terminated Treatment Coronavirus Disease 2019 (COVID‑19) 1 somestatus stop reason just information to hide 3 Terminated Treatment Coronavirus Disease 2019 (COVID‑19) / Seasonal Allergic Rhinitis 1 somestatus stop reason just information to hide 3 Unknown Status Treatment Coronavirus Disease 2019 (COVID‑19) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 194-198 Pharmaceutical and Medical Devices Agency Japan - Predicted Properties
Property Value Source Water Solubility 0.0626 mg/mL ALOGPS logP 1.88 ALOGPS logP 1.51 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 19.54 Chemaxon pKa (Strongest Basic) 8.54 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 134.81 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 117.77 m3·mol-1 Chemaxon Polarizability 41.92 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0900000000-082530f6703612ed3bd1 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0uki-9521000000-d5934cd9fe5aeda04647 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-5950000000-64cc0c66c73f58462655 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-022c-3194000000-0e6b07ec56d42a5940ad Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-006t-4901000000-fddab89c0d8af7bdbe41 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0fdp-3190000000-090e7ca074e860038e12 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 191.08212 predictedDeepCCS 1.0 (2019) [M+H]+ 193.44012 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.1066 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form against all of these substrates
- Specific Function
- metal ion binding
- Gene Name
- PRSS1
- Uniprot ID
- P07477
- Uniprot Name
- Serine protease 1
- Molecular Weight
- 26557.88 Da
References
- Senokuchi K, Nakai H, Nakayama Y, Odagaki Y, Sakaki K, Kato M, Maruyama T, Miyazaki T, Ito H, Kamiyasu K, et al.: New orally active serine protease inhibitors. J Med Chem. 1995 Jul 7;38(14):2521-3. doi: 10.1021/jm00014a003. [Article]
- Tamura Y, Hirado M, Okamura K, Minato Y, Fujii S: Synthetic inhibitors of trypsin, plasmin, kallikrein, thrombin, C1r-, and C1 esterase. Biochim Biophys Acta. 1977 Oct 13;484(2):417-22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Plasma membrane-anchored serine protease that cleaves at arginine residues (PubMed:32703818). Participates in proteolytic cascades of relevance for the normal physiologic function of the prostate (PubMed:25122198). Androgen-induced TMPRSS2 activates several substrates that include pro-hepatocyte growth factor/HGF, the protease activated receptor-2/F2RL1 or matriptase/ST14 leading to extracellular matrix disruption and metastasis of prostate cancer cells (PubMed:15537383, PubMed:25122198, PubMed:26018085). In addition, activates trigeminal neurons and contribute to both spontaneous pain and mechanical allodynia (By similarity)
- Specific Function
- serine-type endopeptidase activity
- Gene Name
- TMPRSS2
- Uniprot ID
- O15393
- Uniprot Name
- Transmembrane protease serine 2
- Molecular Weight
- 53858.845 Da
References
- Hoffmann M, Kleine-Weber H, Schroeder S, Kruger N, Herrler T, Erichsen S, Schiergens TS, Herrler G, Wu NH, Nitsche A, Muller MA, Drosten C, Pohlmann S: SARS-CoV-2 Cell Entry Depends on ACE2 and TMPRSS2 and Is Blocked by a Clinically Proven Protease Inhibitor. Cell. 2020 Apr 16;181(2):271-280.e8. doi: 10.1016/j.cell.2020.02.052. Epub 2020 Mar 5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Exhibits trypsin-like activity as defined by cleavage of synthetic substrates with Arg or Lys as the P1 site (PubMed:10373424). Involved in the terminal differentiation of keratinocytes through prostasin (PRSS8) activation and filaggrin (FLG) processing (PubMed:18843291). Proteolytically cleaves and therefore activates TMPRSS13 (PubMed:28710277)
- Specific Function
- serine-type endopeptidase activity
- Gene Name
- ST14
- Uniprot ID
- Q9Y5Y6
- Uniprot Name
- Suppressor of tumorigenicity 14 protein
- Molecular Weight
- 94769.01 Da
References
- Kitamura K, Tomita K: Proteolytic activation of the epithelial sodium channel and therapeutic application of a serine protease inhibitor for the treatment of salt-sensitive hypertension. Clin Exp Nephrol. 2012 Feb;16(1):44-8. doi: 10.1007/s10157-011-0506-1. Epub 2011 Nov 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- This peptide hormone induces gall bladder contraction and the release of pancreatic enzymes in the gut. Its function in the brain is not clear. Binding to CCK-A receptors stimulates amylase release from the pancreas, binding to CCK-B receptors stimulates gastric acid secretion
- Specific Function
- hormone activity
- Gene Name
- CCK
- Uniprot ID
- P06307
- Uniprot Name
- Cholecystokinin
- Molecular Weight
- 12669.26 Da
References
- Goke B, Printz H, Koop I, Rausch U, Richter G, Arnold R, Adler G: Endogenous CCK release and pancreatic growth in rats after feeding a proteinase inhibitor (camostate). Pancreas. 1986;1(6):509-15. doi: 10.1097/00006676-198611000-00008. [Article]
Drug created at June 23, 2017 20:47 / Updated at February 21, 2021 18:54