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 ;
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) ; Key:UAWXGRJVZSAUSZ-UHFFFAOYSA-N ;
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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

^ 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.
^ 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.
^ Alvaro-Gracia JM (February 2004). "Licofelone--clinical update on a novel LOX/COX inhibitor for the treatment of osteoarthritis". Rheumatology. 43 Suppl 1 (95001): i21-5. doi:10.1093/rheumatology/keh105. PMID 14752172.
^ "Licofelone – Novel Analgesic and Anti-Inflammatory Agent for Osteoarthritis". Retrieved January 12, 2018.
^ 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.

[pmid17704828-1] 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.

[pmid17015640-2] 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.

[pmid14752172-3] Alvaro-Gracia JM (February 2004). "Licofelone--clinical update on a novel LOX/COX inhibitor for the treatment of osteoarthritis". Rheumatology. 43 Suppl 1 (95001): 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.

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