Camostat mesylate
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MedKoo CAT#: 329455

CAS#: 59721-29-8 (mesylate)

Description: Camostat, also known as FOY 305, is a serine protease inhibitor. Camostat is used in the treatment of some forms of cancer and is also effective against some viral infections, as well as inhibiting fibrosis in liver or kidney disease or pancreatitis. It is an inhibitor of the enzyme transmembrane protease, serine 2 (TMPRSS2). Inhibition of TMPRSS2 partially blocked infection by SARS-CoV and Human coronavirus NL63 in HeLa cell cultures. In vitro study showed that camostat significantly reduces the infection of Calu-3 lung cells by SARS-CoV-2, the virus responsible for COVID-19.


Chemical Structure

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Camostat mesylate
CAS# 59721-29-8 (mesylate)

Theoretical Analysis

MedKoo Cat#: 329455
Name: Camostat mesylate
CAS#: 59721-29-8 (mesylate)
Chemical Formula: C21H26N4O8S
Exact Mass:
Molecular Weight: 494.519
Elemental Analysis: C, 51.01; H, 5.30; N, 11.33; O, 25.88; S, 6.48

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500.0mg USD 250.0 Same day
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2.0g USD 750.0 Same day
5.0g USD 1250.0 Same day
10.0g USD 1950.0 Same day
20.0g USD 3050.0 Same day
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Related CAS #: 59721-29-8 (mesylate)   59721-28-7 (free base)  

Synonym: Camostat Mesilate; Camostat Mesylate; FOY 305; FOY-305; FOY305.

IUPAC/Chemical Name: 4-(2-(2-(dimethylamino)-2-oxoethoxy)-2-oxoethyl)phenyl 4-guanidinobenzoate methanesulfonate

InChi Key: FSEKIHNIDBATFG-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(OCC(N(C)C)=O)CC1=CC=C(OC(C2=CC=C(NC(N)=N)C=C2)=O)C=C1.CS(=O)(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Camostat mesylate (Camostat mesilate) is a serine protease, TMPRSS2, prostasin, trypsin, and matriptase inhibitor.
In vitro activity: This study finally compared the antiviral activity of Camostat mesylate and FOY-251, the methanesulfonate of GBPA, in cell culture. The reduced ability of FOY-251 to block the enzymatic activity of recombinant TMPRSS2 as compared to Camostat mesylate would suggest that the compound should also exert reduced antiviral activity. On the other hand, analysis of antiviral activity encompasses preincubation of target cells with Camostat mesylate for 2 h in the presence of FCS, which allows conversion of Camostat mesylate into GBPA, as demonstrated above. Indeed, titration experiments with VSV pseudotypes and Calu-3 lung cells as targets revealed that entry inhibition by FOY-251 was only slightly reduced as compared to Camostat mesylate, with EC50 values of 107 nM (Camostat mesylate) and 178 nM (FOY-251) (Fig. 7). Thus, under the conditions chosen Camostat mesylate and GBPA exerted roughly comparable antiviral activity, likely due to conversion of Camostat mesylate into GBPA. Reference: EBioMedicine. 2021 Mar; 65: 103255. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7930809/
In vivo activity: Next, this study investigated whether CM (Camostat mesylate) could mitigate podocyte injury in MetS. The HS diet decreased the mRNA expression and immunofluorescence staining of podocyte-specific molecules such as nephrin, podocin, and synaptopodin. These changes were significantly recovered by CM, but not by Hyd (Fig. 3A–D). A mean podocyte number per glomerulus was determined by WT-1 positive cells, and its reduction in the HS group was ameliorated only in the HS + CM group (Fig. 3E and F). Next, this study evaluated apoptotic changes of podocytes in those animals. The HS diet increased glomerular apoptotic cells, whereas CM suppressed such changes more efficiently than Hyd (Fig. 4A and B). Furthermore, the immunoblotting analysis demonstrated that CM but not Hyd markedly reduced the apoptotic signals such as the increased Bax/Bcl-2 ratio and cleaved caspase-3 expression, upregulated by the HS diet (Fig. 4C and D). Reference: J Pharmacol Sci. 2021 Aug;146(4):192-199. https://pubmed.ncbi.nlm.nih.gov/34116732/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 74.86 151.38
DMF 25.0 50.55
Ethanol 2.0 4.04
Water 35.91 72.62

Preparing Stock Solutions

The following data is based on the product molecular weight 494.519 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Hoffmann M, Hofmann-Winkler H, Smith JC, Krüger N, Arora P, Sørensen LK, Søgaard OS, Hasselstrøm JB, Winkler M, Hempel T, Raich L, Olsson S, Danov O, Jonigk D, Yamazoe T, Yamatsuta K, Mizuno H, Ludwig S, Noé F, Kjolby M, Braun A, Sheltzer JM, Pöhlmann S. Camostat mesylate inhibits SARS-CoV-2 activation by TMPRSS2-related proteases and its metabolite GBPA exerts antiviral activity. EBioMedicine. 2021 Mar;65:103255. doi: 10.1016/j.ebiom.2021.103255. Epub 2021 Mar 4. PMID: 33676899; PMCID: PMC7930809. 2. Yamaya M, Shimotai Y, Hatachi Y, Lusamba Kalonji N, Tando Y, Kitajima Y, Matsuo K, Kubo H, Nagatomi R, Hongo S, Homma M, Nishimura H. The serine protease inhibitor camostat inhibits influenza virus replication and cytokine production in primary cultures of human tracheal epithelial cells. Pulm Pharmacol Ther. 2015 Aug;33:66-74. doi: 10.1016/j.pupt.2015.07.001. Epub 2015 Jul 10. PMID: 26166259; PMCID: PMC7110702. 3. Mizumoto T, Kakizoe Y, Nakagawa T, Iwata Y, Miyasato Y, Uchimura K, Adachi M, Deng Q, Hayata M, Morinaga J, Miyoshi T, Izumi Y, Kuwabara T, Sakai Y, Tomita K, Kitamura K, Mukoyama M. A serine protease inhibitor camostat mesilate prevents podocyte apoptosis and attenuates podocyte injury in metabolic syndrome model rats. J Pharmacol Sci. 2021 Aug;146(4):192-199. doi: 10.1016/j.jphs.2021.04.003. Epub 2021 Apr 24. PMID: 34116732. 4. Ueda M, Uchimura K, Narita Y, Miyasato Y, Mizumoto T, Morinaga J, Hayata M, Kakizoe Y, Adachi M, Miyoshi T, Shiraishi N, Kadowaki D, Sakai Y, Mukoyama M, Kitamura K. The serine protease inhibitor camostat mesilate attenuates the progression of chronic kidney disease through its antioxidant effects. Nephron. 2015;129(3):223-32. doi: 10.1159/000375308. Epub 2015 Mar 3. PMID: 25766432.
In vitro protocol: 1. Hoffmann M, Hofmann-Winkler H, Smith JC, Krüger N, Arora P, Sørensen LK, Søgaard OS, Hasselstrøm JB, Winkler M, Hempel T, Raich L, Olsson S, Danov O, Jonigk D, Yamazoe T, Yamatsuta K, Mizuno H, Ludwig S, Noé F, Kjolby M, Braun A, Sheltzer JM, Pöhlmann S. Camostat mesylate inhibits SARS-CoV-2 activation by TMPRSS2-related proteases and its metabolite GBPA exerts antiviral activity. EBioMedicine. 2021 Mar;65:103255. doi: 10.1016/j.ebiom.2021.103255. Epub 2021 Mar 4. PMID: 33676899; PMCID: PMC7930809. 2. Yamaya M, Shimotai Y, Hatachi Y, Lusamba Kalonji N, Tando Y, Kitajima Y, Matsuo K, Kubo H, Nagatomi R, Hongo S, Homma M, Nishimura H. The serine protease inhibitor camostat inhibits influenza virus replication and cytokine production in primary cultures of human tracheal epithelial cells. Pulm Pharmacol Ther. 2015 Aug;33:66-74. doi: 10.1016/j.pupt.2015.07.001. Epub 2015 Jul 10. PMID: 26166259; PMCID: PMC7110702.
In vivo protocol: 1. Mizumoto T, Kakizoe Y, Nakagawa T, Iwata Y, Miyasato Y, Uchimura K, Adachi M, Deng Q, Hayata M, Morinaga J, Miyoshi T, Izumi Y, Kuwabara T, Sakai Y, Tomita K, Kitamura K, Mukoyama M. A serine protease inhibitor camostat mesilate prevents podocyte apoptosis and attenuates podocyte injury in metabolic syndrome model rats. J Pharmacol Sci. 2021 Aug;146(4):192-199. doi: 10.1016/j.jphs.2021.04.003. Epub 2021 Apr 24. PMID: 34116732. 2. Ueda M, Uchimura K, Narita Y, Miyasato Y, Mizumoto T, Morinaga J, Hayata M, Kakizoe Y, Adachi M, Miyoshi T, Shiraishi N, Kadowaki D, Sakai Y, Mukoyama M, Kitamura K. The serine protease inhibitor camostat mesilate attenuates the progression of chronic kidney disease through its antioxidant effects. Nephron. 2015;129(3):223-32. doi: 10.1159/000375308. Epub 2015 Mar 3. PMID: 25766432.

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1: Hoffmann M, Hofmann-Winkler H, Smith JC, Krüger N, Sørensen LK, Søgaard OS, Hasselstrøm JB, Winkler M, Hempel T, Raich L, Olsson S, Yamazoe T, Yamatsuta K, Mizuno H, Ludwig S, Noé F, Sheltzer JM, Kjolby M, Pöhlmann S. Camostat mesylate inhibits SARS-CoV-2 activation by TMPRSS2-related proteases and its metabolite GBPA exerts antiviral activity. bioRxiv [Preprint]. 2020 Aug 5:2020.08.05.237651. doi: 10.1101/2020.08.05.237651. PMID: 32793911; PMCID: PMC7418737.

2: Bittmann S, Weissenstein A, Villalon G, Moschuring-Alieva E, Luchter E. Simultaneous Treatment of COVID-19 With Serine Protease Inhibitor Camostat and/or Cathepsin L Inhibitor? J Clin Med Res. 2020 May;12(5):320-322. doi: 10.14740/jocmr4161. Epub 2020 May 8. PMID: 32489508; PMCID: PMC7239585.

3: Uno Y. Camostat mesilate therapy for COVID-19. Intern Emerg Med. 2020 Apr 29:1–2. doi: 10.1007/s11739-020-02345-9. Epub ahead of print. PMID: 32347443; PMCID: PMC7188520.

4: Ramsey ML, Nuttall J, Hart PA; TACTIC Investigative Team. A phase 1/2 trial to evaluate the pharmacokinetics, safety, and efficacy of NI-03 in patients with chronic pancreatitis: study protocol for a randomized controlled trial on the assessment of camostat treatment in chronic pancreatitis (TACTIC). Trials. 2019 Aug 14;20(1):501. doi: 10.1186/s13063-019-3606-y. PMID: 31412955; PMCID: PMC6694471.

5: Yamawaki H, Futagami S, Kaneko K, Agawa S, Higuchi K, Murakami M, Wakabayashi M, Sakasegawa N, Kodaka Y, Ueki N, Gudis K, Kawamoto C, Iwakiri K. Camostat Mesilate, Pancrelipase, and Rabeprazole Combination Therapy Improves Epigastric Pain in Early Chronic Pancreatitis and Functional Dyspepsia with Pancreatic Enzyme Abnormalities. Digestion. 2019;99(4):283-292. doi: 10.1159/000492813. Epub 2018 Nov 2. PMID: 30391941.

6: 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. PMID: 27408783; PMCID: PMC4925915.

7: Narita Y, Ueda M, Uchimura K, Kakizoe Y, Miyasato Y, Mizumoto T, Morinaga J, Hayata M, Nakagawa T, Adachi M, Miyoshi T, Sakai Y, Kadowaki D, Hirata S, Mukoyama M, Kitamura K. Combination therapy with renin-angiotensin-aldosterone system inhibitor telmisartan and serine protease inhibitor camostat mesilate provides further renoprotection in a rat chronic kidney disease model. J Pharmacol Sci. 2016 Feb;130(2):110-6. doi: 10.1016/j.jphs.2016.01.003. Epub 2016 Jan 20. PMID: 26887332.

8: Yamaya M, Shimotai Y, Hatachi Y, Lusamba Kalonji N, Tando Y, Kitajima Y, Matsuo K, Kubo H, Nagatomi R, Hongo S, Homma M, Nishimura H. The serine protease inhibitor camostat inhibits influenza virus replication and cytokine production in primary cultures of human tracheal epithelial cells. Pulm Pharmacol Ther. 2015 Aug;33:66-74. doi: 10.1016/j.pupt.2015.07.001. Epub 2015 Jul 10. PMID: 26166259; PMCID: PMC7110702.

9: Ueda M, Uchimura K, Narita Y, Miyasato Y, Mizumoto T, Morinaga J, Hayata M, Kakizoe Y, Adachi M, Miyoshi T, Shiraishi N, Kadowaki D, Sakai Y, Mukoyama M, Kitamura K. The serine protease inhibitor camostat mesilate attenuates the progression of chronic kidney disease through its antioxidant effects. Nephron. 2015;129(3):223-32. doi: 10.1159/000375308. Epub 2015 Mar 3. PMID: 25766432.

10: Zhao J, Wang Z, Zou B, Song Y, Dong L. [Camostat mesilate, a protease inhibitor, inhibits visceral sensitivity and spinal c-fos expression in rats with acute restraint stress]. Nan Fang Yi Ke Da Xue Xue Bao. 2014 Oct;34(10):1546-50. Chinese. PMID: 25345960.

11: Rowe SM, Reeves G, Hathorne H, Solomon GM, Abbi S, Renard D, Lock R, Zhou P, Danahay H, Clancy JP, Waltz DA. Reduced sodium transport with nasal administration of the prostasin inhibitor camostat in subjects with cystic fibrosis. Chest. 2013 Jul;144(1):200-207. doi: 10.1378/chest.12-2431. PMID: 23412700; PMCID: PMC3707174.

12: Takahagi S, Shindo H, Watanabe M, Kameyoshi Y, Hide M. Refractory chronic urticaria treated effectively with the protease inhibitors, nafamostat mesilate and camostat mesilate. Acta Derm Venereol. 2010 Jul;90(4):425-6. doi: 10.2340/00015555-0869. PMID: 20574618.

13: Sai JK, Suyama M, Kubokawa Y, Matsumura Y, Inami K, Watanabe S. Efficacy of camostat mesilate against dyspepsia associated with non-alcoholic mild pancreatic disease. J Gastroenterol. 2010 Mar;45(3):335-41. doi: 10.1007/s00535-009-0148-1. Epub 2009 Oct 30. PMID: 19876587.

14: Coote K, Atherton-Watson HC, Sugar R, Young A, MacKenzie-Beevor A, Gosling M, Bhalay G, Bloomfield G, Dunstan A, Bridges RJ, Sabater JR, Abraham WM, Tully D, Pacoma R, Schumacher A, Harris J, Danahay H. Camostat attenuates airway epithelial sodium channel function in vivo through the inhibition of a channel- activating protease. J Pharmacol Exp Ther. 2009 May;329(2):764-74. doi: 10.1124/jpet.108.148155. Epub 2009 Feb 3. PMID: 19190233.

15: Maekawa A, Kakizoe Y, Miyoshi T, Wakida N, Ko T, Shiraishi N, Adachi M, Tomita K, Kitamura K. Camostat mesilate inhibits prostasin activity and reduces blood pressure and renal injury in salt-sensitive hypertension. J Hypertens. 2009 Jan;27(1):181-9. doi: 10.1097/hjh.0b013e328317a762. PMID: 19145783.

16: Raboin SJ, Reeve JR Jr, Cooper MS, Green GM, Sayegh AI. Activation of submucosal but not myenteric plexus of the gastrointestinal tract accompanies reduction of food intake by camostat. Regul Pept. 2008 Oct 9;150(1-3):73-80. doi: 10.1016/j.regpep.2008.06.007. Epub 2008 Jun 23. PMID: 18620003.

17: Ishikura H, Nishimura S, Matsunami M, Tsujiuchi T, Ishiki T, Sekiguchi F, Naruse M, Nakatani T, Kamanaka Y, Kawabata A. The proteinase inhibitor camostat mesilate suppresses pancreatic pain in rodents. Life Sci. 2007 May 1;80(21):1999-2004. doi: 10.1016/j.lfs.2007.02.044. Epub 2007 Mar 12. PMID: 17433371.

18: Ashizawa N, Hashimoto T, Miyake T, Shizuku T, Imaoka T, Kinoshita Y. Efficacy of camostat mesilate compared with famotidine for treatment of functional dyspepsia: is camostat mesilate effective? J Gastroenterol Hepatol. 2006 Apr;21(4):767-71. doi: 10.1111/j.1440-1746.2005.04041.x. PMID: 16677167.

19: Yin J, Noda Y, Yotsuyanagi T. Properties of poly(lactic-co-glycolic acid) nanospheres containing protease inhibitors: camostat mesilate and nafamostat mesilate. Int J Pharm. 2006 May 11;314(1):46-55. doi: 10.1016/j.ijpharm.2006.01.047. Epub 2006 Feb 23. PMID: 16551494.

20: Yin J, Noda Y, Hazemoto N, Yotsuyanagi T. Distribution of protease inhibitors in lipid emulsions: gabexate mesilate and camostat mesilate. Chem Pharm Bull (Tokyo). 2005 Aug;53(8):893-8. doi: 10.1248/cpb.53.893. PMID: 16079515.



Additional Information

Related CAS#
CAS#59721-28-7 (Camostat)
59721-29-8 (Camostat mesilate)