Licofelone

Licofelone

Names
IUPAC name [6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid
Identifiers
CAS Number	156897-06-2
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL52854
ChemSpider	117391
ECHA InfoCard	100.222.821
PubChem	133021
UNII	P5T6BYS22Y
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) Key: UAWXGRJVZSAUSZ-UHFFFAOYSA-N InChI=1/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) Key: UAWXGRJVZSAUSZ-UHFFFAOYAP
SMILES CC1(CC2=C(C(=C(N2C1)CC(=O)O)C3=CC=C(C=C3)Cl)C4=CC=CC=C4)C
Properties
Chemical formula	C23H22ClNO2
Molar mass	379.879 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Licofelone is a dual COX/LOX inhibitor^[1][2] being considered as a treatment for osteoarthritis^[3] and which is under development by Merckle GmbH with partners Alfa Wassermann and Lacer.

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. It has passed the phase III trials.^[4]

References

1. Fischer L, Hornig M, Pergola C, et al. (October 2007). "The molecular mechanism of the inhibition by licofelone of the biosynthesis of 5-lipoxygenase products". British Journal of Pharmacology. 152 (4): 471–80. doi:10.1038/sj.bjp.0707416. PMC 2050828. PMID 17704828.
2. Vidal C, Gómez-Hernández A, Sánchez-Galán E, et al. (January 2007). "Licofelone, a balanced inhibitor of cyclooxygenase and 5-lipoxygenase, reduces inflammation in a rabbit model of atherosclerosis". The Journal of Pharmacology and Experimental Therapeutics. 320 (1): 108–16. doi:10.1124/jpet.106.110361. PMID 17015640.
3. Alvaro-Gracia JM (February 2004). "Licofelone--clinical update on a novel LOX/COX inhibitor for the treatment of osteoarthritis". Rheumatology (Oxford, England). 43 Suppl 1 (90001): i21–5. doi:10.1093/rheumatology/keh105. PMID 14752172.
4. http://www.drugdevelopment-technology.com/projects/licofelone/