Drug Information

Drug General Information
Drug ID
D0N1SU
Former ID
DCL000302
Drug Name
Licofelone
Synonyms
LCF; Licofelone [INN]; ML 3000; ML-3000; [6-(4-CHLOROPHENYL)-2,2-DIMETHYL-7-PHENYL-2,3-DIHYDRO-1H-PYRROLIZIN-5-YL]ACETIC ACID; (2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetic acid; (6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid; 2,2-Dimethyl-6-(4-chlorophenyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetic acid; 2,3-Dihydro-6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-acetic acid; 2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid; 6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-acetic acid
Drug Type
Small molecular drug
Indication Osteoarthritis [ICD9: 715; ICD10:M15-M19, M47] Discontinued in Phase 1 [545621]
Company
Merckle GmbH
Structure
Download
2D MOL

3D MOL
Formula
C23H22ClNO2
Canonical SMILES
CC1(CC2=C(C(=C(N2C1)CC(=O)O)C3=CC=C(C=C3)Cl)C4=CC=CC=C4<br />)C
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
CAS Number
CAS 156897-06-2
PubChem Compound ID
133021
PubChem Substance ID
6436380, 7888616, 10243273, 12014886, 14829304, 29311030, 50040041, 50700417, 53788587, 57344354, 103243188, 103945934, 104378798, 125333743, 126645607, 126648934, 129342134, 131300446, 134338958, 135088300, 135692433, 137116560, 137275875, 142116170, 144072480, 162172234, 162476140, 163884604, 164228207, 164761582, 175426859, 184826912, 196105884, 198972330, 204370171, 223392829, 223705238, 223909705, 226588726, 251882412, 252215695, 252450609
Target and Pathway
Target(s) Arachidonate 5-lipoxygenase Target Info Inhibitor [535517], [536541], [536548], [536629]
BioCyc Pathway Aspirin-triggered lipoxin biosynthesis
Resolvin D biosynthesis
Leukotriene biosynthesis
Lipoxin biosynthesis
Aspirin triggered resolvin D biosynthesis
Aspirin triggered resolvin E biosynthesis
KEGG Pathway Arachidonic acid metabolism
Metabolic pathways
Serotonergic synapse
Ovarian steroidogenesis
Toxoplasmosis
NetPath Pathway IL4 Signaling Pathway
PathWhiz Pathway Arachidonic Acid Metabolism
WikiPathways Vitamin D Receptor Pathway
Arachidonic acid metabolism
Eicosanoid Synthesis
Selenium Micronutrient Network
References
Ref 545621Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800003927)
Ref 535517Licofelone (ML-3000), a dual inhibitor of 5-lipoxygenase and cyclooxygenase, reduces the level of cartilage chondrocyte death in vivo in experimental dog osteoarthritis: inhibition of pro-apoptotic factors. J Rheumatol. 2002 Jul;29(7):1446-53.
Ref 536541Licofelone, a dual COX/5-LOX inhibitor, induces apoptosis in HCA-7 colon cancer cells through the mitochondrial pathway independently from its ability to affect the arachidonic acid cascade. Carcinogenesis. 2008 Feb;29(2):371-80. Epub 2007 Nov 21.
Ref 536548Activity and potential role of licofelone in the management of osteoarthritis. Clin Interv Aging. 2007;2(1):73-9.
Ref 536629Cyclooxygenase (COX) and 5-lipoxygenase (5-LOX) selectivity of COX inhibitors. Prostaglandins Leukot Essent Fatty Acids. 2008 Feb;78(2):99-108. Epub 2008 Feb 15.

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