Licofelone (ML3000, Compound 3e) is a dual inhibitor of COX and 5-lipoxygenase (5-LOX), with corresponding IC50 values of 0.21 μM and 0.18 μM, respectively. Licofelone can induce apoptosis and reduce the production of proinflammatory leukotrienes and prostaglandins. Licofelone can be used to treat osteoarthritis.

 

Brand: BCM

 

Target: Apoptosis; Lipoxygenase; COX

 

Signaling Pathways: Apoptosis; Immunology/Inflammation; Metabolism; Neuroscience

 

In Vitro: The dual COX/5-LOX inhibitor licofelone triggers apoptosis in a dose- and time-dependent manner in HCA-7 colon cancer cells.?Induction of apoptosis was related to the recruitment of the intrinsic mitochondrial apoptotic pathway, as shown by loss in mitochondrial membrane potential, cytochrome c release, caspase-9 and 3 activation and poly-(ADP-ribose)polymerase-1 cleavage.?Moreover, licofelone induced the cleavage of the full-length p21(Bax) into p18(Bax), a more potent inducer of the apoptotic process than the uncleaved form.?Pre-treatment of HCA-7 cells with the pan-caspase inhibitor z-VAD-fmk significantly blocked licofelone-induced apoptosis, confirming that this process occurred primarily in a caspase-dependent pathway.?Licofelone was able to affect the arachidonic acid (AA) cascade, as it blocked the activity of 5-LOX and COX enzymes, and it induced, through the phosphorylation of cytoplasmic phospholipase A(2) (cPLA(2)), the release of unesterified AA from HCA-7 membrane phospholipids.

 

Melting Point: 162-163°C

 

Boiling Point: 539.7±50.0 °C(Predicted)

 

pKa: 4.47±0.10(Predicted)

 

Solubility: Soluble in DMSO; Soluble in Ethanol. Insoluble in Water.

 

GHS: GHS07

 

Isomeric SMILES: CC1(CC2=C(C(=C(N2C1)CC(=O)O)C3=CC=C(C=C3)Cl)C4=CC=CC=C4)C  

 

InChIKey: UAWXGRJVZSAUSZ-UHFFFAOYSA-N  

 

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)

 

Attribute
[Chem Name]	2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid
[Synonym]	Licofelone; ML3000
[CAS No.]	156897-06-2
[EINECS]	694-581-3
[MDL No.]	MFCD00929900
[Formula]	C23H22ClNO2
[Molecular]	379.88
[Form]	Off-White to Light Yellow Solid
[Storage]	Sealed in dry. Store in freezer, under -20°C

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