Mofezolac

Last updated
Mofezolac
Mofezolac.png
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • [3,4-bis(4-methoxyphenyl)isoxazol-5-yl]acetic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
Formula C19H17NO5
Molar mass 339.347 g·mol−1
3D model (JSmol)
  • COC1=CC=C(C=C1)C2=C(ON=C2C3=CC=C(C=C3)OC)CC(=O)O
  • InChI=1S/C19H17NO5/c1-23-14-7-3-12(4-8-14)18-16(11-17(21)22)25-20-19(18)13-5-9-15(24-2)10-6-13/h3-10H,11H2,1-2H3,(H,21,22)
  • Key:DJEIHHYCDCTAAH-UHFFFAOYSA-N
   (verify)

Mofezolac (INN), sold under the name Disopain in Japan, is a nonsteroidal anti-inflammatory drug (NSAID) used for its analgesic and anti-inflammatory actions. It is often prescribed for rheumatoid arthritis, lower back pain, frozen shoulder, and pain management after surgery or trauma. [1] It is also being investigated for potential use in the treatment of neuroinflammation. [2] [3]

Common side effects include abdominal pain, stomach discomfort, nausea, sleepiness, itch, hives, rash, erythema, and edema. Serious side effects include peptic ulcers, gastrointestinal bleeding, asthma attack, jaundice, acute liver failure, and thrombocytopenia. [1] Use is not recommended during pregnancy or breastfeeding. [4]

Mofezolac acts via selective inhibition of the cyclooxygenase COX-1 and consequent suppression of prostaglandin synthesis. [5] It is the most potent and selective reversible COX-1 inhibitor. [6] Studies of ovine COX-1 in complex with mofezolac indicate that the drug forms a combination of electrostatic, H-bond, hydrophobic, and van der Waals contacts with the enzyme active site channel, contributing to mofezolac's high binding affinity. [7]

Mofezolac belongs to the class of isoxazoles and is a substrate of CYP2C9. [8]

It is manufactured and marketed by Nipro ES Pharma Co., Ltd. [1]

Related Research Articles

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Cyclooxygenases are enzymes that take part in a complex biosynthetic cascade that results in the conversion of polyunsaturated fatty acids to prostaglandins and thromboxane(s). Their main role is to catalyze the transformation of arachidonic acid into the intermediate prostaglandin H2, which is the precursor of a variety of prostanoids with diverse and potent biological actions. Cyclooxygenases have two main isoforms that are called COX-1 and COX-2. COX-1 is responsible for the synthesis of prostaglandin and thromboxane in many types of cells, including the gastro-intestinal tract and blood platelets. COX-2 plays a major role in prostaglandin biosynthesis in inflammatory cells and in the central nervous system. Prostaglandin synthesis in these sites is a key factor in the development of inflammation and hyperalgesia. COX-2 inhibitors have analgesic and anti-inflammatory activity by blocking the transformation of arachidonic acid into prostaglandin H2 selectively.

References

  1. 1 2 3 "Kusuri-no-Shiori (Drug Information Sheet)". RAD-AR Council, Japan. June 2018. Retrieved 2021-10-18.
  2. ↑ Calvello R, Panaro MA, Carbone ML, Cianciulli A, Perrone MG, Vitale P, et al. (January 2012). "Novel selective COX-1 inhibitors suppress neuroinflammatory mediators in LPS-stimulated N13 microglial cells". Pharmacological Research. 65 (1): 137–148. doi:10.1016/j.phrs.2011.09.009. hdl: 11586/117804 . PMID   22001217.
  3. ↑ Calvello R, Lofrumento DD, Perrone MG, Cianciulli A, Salvatore R, Vitale P, et al. (2017). "Highly Selective Cyclooxygenase-1 Inhibitors P6 and Mofezolac Counteract Inflammatory State both In Vitro and In Vivo Models of Neuroinflammation". Frontiers in Neurology. 8: 251. doi: 10.3389/fneur.2017.00251 . PMC   5465243 . PMID   28649222.
  4. ↑ "Pharmaceuticals and Medical Devices Safety Information" (381). Translated by Pharmaceuticals and Medical Devices Agency. Japan Ministry of Health, Labour and Welfare. March 2021.{{cite journal}}: Cite journal requires |journal= (help)
  5. ↑ Ono N, Yamamoto N, Sunami A, Yamasaki Y, Miyake H (February 1990). "[Pharmacological profile of mofezolac, a new non-steroidal analgesic anti-inflammatory drug]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 95 (2): 63–81. doi: 10.1254/fpj.95.2_63 . PMID   2109726.
  6. ↑ Pati ML, Vitale P, Ferorelli S, Iaselli M, Miciaccia M, Boccarelli A, et al. (February 2019). "Translational impact of novel widely pharmacological characterized mofezolac-derived COX-1 inhibitors combined with bortezomib on human multiple myeloma cell lines viability". European Journal of Medicinal Chemistry. 164: 59–76. doi:10.1016/j.ejmech.2018.12.029. hdl: 11586/227733 . PMID   30590258. S2CID   58648199.
  7. ↑ Cingolani G, Panella A, Perrone MG, Vitale P, Di Mauro G, Fortuna CG, et al. (September 2017). "Structural basis for selective inhibition of Cyclooxygenase-1 (COX-1) by diarylisoxazoles mofezolac and 3-(5-chlorofuran-2-yl)-5-methyl-4-phenylisoxazole (P6)". European Journal of Medicinal Chemistry. 138: 661–668. doi:10.1016/j.ejmech.2017.06.045. PMC   5992922 . PMID   28710965.
  8. ↑ "DRUG: Mofezolac". KEGG. Retrieved 2021-10-18.


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