:Licofelone

{{Short description|Analgesic and anti-inflammatory compound}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 376409282

| drug_name =

| INN =

| type =

| IUPAC_name = [6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid

| image = Licofelone_structure.svg

| alt =

| caption =

| pronounce =

| tradename =

| Drugs.com =

| MedlinePlus =

| pregnancy_AU =

| pregnancy_AU_comment =

| pregnancy_US =

| pregnancy_category=

| routes_of_administration =

| legal_AU =

| legal_AU_comment =

| legal_BR =

| legal_BR_comment =

| legal_CA =

| legal_DE =

| legal_NZ =

| legal_UK =

| legal_US =

| legal_UN =

| legal_status = Investigational

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| onset =

| elimination_half-life =

| duration_of_action =

| excretion =

| CAS_number = 156897-06-2

| class =

| ATCvet =

| ATC_prefix =

| ATC_suffix =

| DrugBank =

| UNII = P5T6BYS22Y

| PubChem=133021

| ChEMBL = 52854

| ChEBI = 47532

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 117391

| C=23|H=22|Cl=1|N=1|O=2

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = UAWXGRJVZSAUSZ-UHFFFAOYSA-N

}}

Licofelone is a dual COX/LOX inhibitor{{cite journal | vauthors = Fischer L, Hornig M, Pergola C, Meindl N, Franke L, Tanrikulu Y, Dodt G, Schneider G, Steinhilber D, Werz O | display-authors = 6 | title = The molecular mechanism of the inhibition by licofelone of the biosynthesis of 5-lipoxygenase products | journal = British Journal of Pharmacology | volume = 152 | issue = 4 | pages = 471–80 | date = October 2007 | pmid = 17704828 | pmc = 2050828 | doi = 10.1038/sj.bjp.0707416 }}{{cite journal | vauthors = Vidal C, Gómez-Hernández A, Sánchez-Galán E, González A, Ortega L, Gómez-Gerique JA, Tuñón J, Egido J | display-authors = 6 | title = Licofelone, a balanced inhibitor of cyclooxygenase and 5-lipoxygenase, reduces inflammation in a rabbit model of atherosclerosis | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 320 | issue = 1 | pages = 108–16 | date = January 2007 | pmid = 17015640 | doi = 10.1124/jpet.106.110361 | s2cid = 73105840 }} that was studied in clinical trials as a treatment for osteoarthritis{{cite journal | vauthors = Alvaro-Gracia JM | title = Licofelone--clinical update on a novel LOX/COX inhibitor for the treatment of osteoarthritis | journal = Rheumatology | volume = 43 Suppl 1 | issue = 90001 | pages = i21-5 | date = February 2004 | pmid = 14752172 | doi = 10.1093/rheumatology/keh105 | doi-access = free }} 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,{{cite web | url = http://www.drugdevelopment-technology.com/projects/licofelone/ | title = Licofelone – Novel Analgesic and Anti-Inflammatory Agent for Osteoarthritis | access-date = January 12, 2018}}{{cite journal | vauthors = Wildi LM, Raynauld JP, Martel-Pelletier J, Abram F, Dorais M, Pelletier JP | title = Relationship between bone marrow lesions, cartilage loss and pain in knee osteoarthritis: results from a randomised controlled clinical trial using MRI | journal = Annals of the Rheumatic Diseases | volume = 69 | issue = 12 | pages = 2118–24 | date = December 2010 | pmid = 20610445 | doi = 10.1136/ard.2009.127993 | s2cid = 206864399 }} but results were mixed and the drug has never been submitted for regulatory approval.