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Mofezolac

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Chemical compound Pharmaceutical compound
Mofezolac
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • acetic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H17NO5
Molar mass339.347 g·mol
3D model (JSmol)
SMILES
  • COC1=CC=C(C=C1)C2=C(ON=C2C3=CC=C(C=C3)OC)CC(=O)O
InChI
  • 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. It is also being investigated for potential use in the treatment of neuroinflammation.

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. Use is not recommended during pregnancy or breastfeeding.

Mofezolac acts via selective inhibition of the cyclooxygenase COX-1 and consequent suppression of prostaglandin synthesis. It is the most potent and selective reversible COX-1 inhibitor. 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.

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

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

References

  1. ^ "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.
Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key: underline indicates initially developed first-in-class compound of specific group; WHO-Essential Medicines; withdrawn drugs; veterinary use.
Prostanoid signaling modulators
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F2α)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthaseHQL-79
PGFSTooltip Prostaglandin F synthaseBimatoprost
PGI2STooltip Prostacyclin synthaseTranylcypromine
TXASTooltip Thromboxane A synthase
Others
See also
Receptor/signaling modulators
Leukotriene signaling modulators


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