Licofelone

• CAT Number: R009348
• CAS Number: 156897-06-2
• Molecular Formula: C23H22ClNO2
• Molecular Weight: 379.884
• Purity: ≥95%
• Synonyms: 6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-?1H-pyrrolizine-5-acetic Acid; ML-3000
• Target: COX
• Solubility: Soluble in DMSO > 10 mM
• Storage: Store at -20C
• IUPAC Name: 2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid
• InChI: InChI=1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)
• InChIKey: UAWXGRJVZSAUSZ-UHFFFAOYSA-N
• SMILES: CC1(CC2=C(C(=C(N2C1)CC(=O)O)C3=CC=C(C=C3)Cl)C4=CC=CC=C4)C

Licofelone, also known as ML-3000, is a dual COX/LOX inhibitor potentially for the treatment of osteoarthritis. Licofelone is both an analgesic and an anti-inflammatory. Inhibition of 5-LOX may reduce the gastrointestinal toxicity associated with other non-steroidal anti-inflammatory drugs, which only inhibit COX (cyclooxygenase). Licofelone is the first drug to inhibit both.

Reference

1:Anticonvulsive Effects of Licofelone on Status Epilepticus Induced by Lithium-pilocarpine in Wistar Rats: a Role for Inducible Nitric Oxide Synthase. Eslami SM, Moradi MM, Ghasemi M, Dehpour AR.J Epilepsy Res. 2016 Dec 31;6(2):51-58. doi: 10.14581/jer.16011. eCollection 2016 Dec. PMID: 28101475 Free PMC Article2:Improved Antitumor Activity of a Therapeutic Melanoma Vaccine through the Use of the Dual COX-2/5-LO Inhibitor Licofelone. Neumann S, Shirley SA, Kemp RA, Hook SM.Front Immunol. 2016 Dec 5;7:537. eCollection 2016. PMID: 27994586 Free PMC Article3:A COX/5-LOX Inhibitor Licofelone Revealed Anticonvulsant Properties Through iNOS Diminution in Mice. Payandemehr B, Khoshneviszadeh M, Varastehmoradi B, Gholizadeh R, Bahremand T, Attar H, Bahremand A, Dehpour AR.Neurochem Res. 2015 Sep;40(9):1819-28. doi: 10.1007/s11064-015-1669-z. Epub 2015 Jul 28. PMID: 26216049 4:Modulation by licofelone and celecoxib of experimentally induced cancer and preneoplastic lesions in mice exposed to cigarette smoke. Balansky R, Ganchev G, Iltcheva M, Nikolov M, La Maestra S, Micale RT, D/’Agostini F, Steele VE, De Flora S.Curr Cancer Drug Targets. 2015;15(3):188-95. PMID: 25687474 5:Effect of licofelone–a dual COX/5-LOX inhibitor in intracerebroventricular streptozotocin-induced behavioral and biochemical abnormalities in rats. Kumar A, Sharma S, Prashar A, Deshmukh R.J Mol Neurosci. 2015 Mar;55(3):749-59. doi: 10.1007/s12031-014-0414-4. Epub 2014 Sep 10. PMID: 25204299 6:Immunomodulatory effectiveness of licofelone in preventing epidural fibrosis in post-laminectomy rat. Zhang K, Zhao J, Su W, Lu R, Lv P.Eur J Orthop Surg Traumatol. 2015 Jul;25 Suppl 1:S63-8. doi: 10.1007/s00590-014-1534-9. Epub 2014 Sep 9. PMID: 25200318 7:Chemoprevention of urothelial cell carcinoma growth and invasion by the dual COX-LOX inhibitor licofelone in UPII-SV40T transgenic mice. Madka V, Mohammed A, Li Q, Zhang Y, Patlolla JM, Biddick L, Lightfoot S, Wu XR, Steele V, Kopelovich L, Rao CV.Cancer Prev Res (Phila). 2014 Jul;7(7):708-16. doi: 10.1158/1940-6207.CAPR-14-0087. Epub 2014 May 2. PMID: 24795386 Free PMC Article8:Cytotoxic and apoptotic functions of licofelone on rat glioma cells. Kus G, Oztopcu-Vatan P, Uyar R, Kabadere S.Acta Biol Hung. 2013 Dec;64(4):438-52. doi: 10.1556/ABiol.64.2013.4.4. PMID: 24275590 9:Licofelone abolishes survival of carcinogenic fibroblasts by inducing apoptosis. Kabadere S, Kus G, Uyar R, Oztopcu-Vatan P.Drug Chem Toxicol. 2014 Jan;37(1):1-7. doi: 10.3109/01480545.2013.806525. Epub 2013 Jul 8. PMID: 23834160 10:Licofelone modulates neuroinflammation and attenuates mechanical hypersensitivity in the chronic phase of spinal cord injury. Dulin JN, Karoly ED, Wang Y, Strobel HW, Grill RJ.J Neurosci. 2013 Jan 9;33(2):652-64. doi: 10.1523/JNEUROSCI.6128-11.2013. PMID: 23303944 Free PMC Article