Licofelone

Licofelone

Legal status
Legal status	Investigational
Identifiers
IUPAC name [6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid
CAS Number	156897-06-2
PubChem CID	133021
ChemSpider	117391  N
UNII	P5T6BYS22Y
ChEBI	CHEBI:47532
ChEMBL	ChEMBL52854
CompTox Dashboard (EPA)	DTXSID40166154
ECHA InfoCard	100.222.821
Chemical and physical data
Formula	C23H22ClNO2
Molar mass	379.88 g·mol−1
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) N Key:UAWXGRJVZSAUSZ-UHFFFAOYSA-N N
NY  (what is this?)    (verify)

Licofelone is a dual COX/LOX inhibitor ^{[1] [2]} that was studied in clinical trials as a treatment for osteoarthritis ^[3] and which was under development by Merckle GmbH with partners Alfa Wassermann and Lacer.

Licofelone is both an analgesic and an anti-inflammatory. Inhibition of 5-lipoxygenase (5-LOX) may reduce the gastrointestinal toxicity associated with other nonsteroidal anti-inflammatory drugs (NSAID), which only inhibit cyclooxygenase (COX). Licofelone is the first drug to inhibit both.

Phase III trials for osteoarthritis were conducted in the early 2000s, ^{[4] [5]} but results were mixed and the drug has never been submitted for regulatory approval.

References

1. Fischer L, Hornig M, Pergola C, Meindl N, Franke L, Tanrikulu Y, 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, González A, Ortega L, Gómez-Gerique JA, 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. S2CID   73105840.
3. Alvaro-Gracia JM (February 2004). "Licofelone--clinical update on a novel LOX/COX inhibitor for the treatment of osteoarthritis". Rheumatology. 43 Suppl 1 (90001): i21-5. doi: 10.1093/rheumatology/keh105 . PMID   14752172.
4. "Licofelone – Novel Analgesic and Anti-Inflammatory Agent for Osteoarthritis" . Retrieved January 12, 2018.
5. Wildi LM, Raynauld JP, Martel-Pelletier J, Abram F, Dorais M, Pelletier JP (December 2010). "Relationship between bone marrow lesions, cartilage loss and pain in knee osteoarthritis: results from a randomised controlled clinical trial using MRI". Annals of the Rheumatic Diseases. 69 (12): 2118–24. doi:10.1136/ard.2009.127993. PMID   20610445. S2CID   206864399.