LCF

[6-(4-CHLOROPHENYL)-2,2-DIMETHYL-7-PHENYL-2,3-DIHYDRO-1H-PYRROLIZIN-5-YL]ACETIC ACID

Created:	2005-06-14
Last modified:	2020-06-05

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2 entries where LCF is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	49
Chiral Atom Count	0
Bond Count	52
Aromatic Bond Count	19

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Chemical Component Summary
Name	[6-(4-CHLOROPHENYL)-2,2-DIMETHYL-7-PHENYL-2,3-DIHYDRO-1H-PYRROLIZIN-5-YL]ACETIC ACID
Synonyms	LICOFELONE
Systematic Name (OpenEye OEToolkits)	2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]ethanoic acid
Formula	C₂₃ H₂₂ Cl N O₂
Molecular Weight	379.879
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	Clc4ccc(c1c(n3c(c1c2ccccc2)CC(C)(C3)C)CC(=O)O)cc4
SMILES	CACTVS	3.341	CC1(C)Cn2c(CC(O)=O)c(c3ccc(Cl)cc3)c(c4ccccc4)c2C1
SMILES	OpenEye OEToolkits	1.5.0	CC1(Cc2c(c(c(n2C1)CC(=O)O)c3ccc(cc3)Cl)c4ccccc4)C
Canonical SMILES	CACTVS	3.341	CC1(C)Cn2c(CC(O)=O)c(c3ccc(Cl)cc3)c(c4ccccc4)c2C1
Canonical SMILES	OpenEye OEToolkits	1.5.0	CC1(Cc2c(c(c(n2C1)CC(=O)O)c3ccc(cc3)Cl)c4ccccc4)C
InChI	InChI	1.03	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	InChI	1.03	UAWXGRJVZSAUSZ-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB04725
Name	Licofelone
Groups	investigational
Description	Developed by the German pharmaceutical company, Merckle GmbH, together with EuroAlliance partners Alfa Wassermann and Lacer, licofelone (ML3000) is a dual COX/LOX inhibitor and the first member of this new class of analgesic and anti-inflammatory drugs. It is currently under evaluation as a treatment for osteoarthritis (OA), the most common form of arthritis. Although phase III trials have been successfully completed in OA patients no dates for regulatory submission have yet been given.
Synonyms	Licofelone
Indication	For the management of osteoarthritis.
Categories	Analgesics Analgesics, Non-Narcotic Anti-Inflammatory Agents Anti-Inflammatory Agents, Non-Steroidal Antirheumatic Agents Central Nervous System Agents Cyclooxygenase Inhibitors Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (strength unknown) Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Enzyme Inhibitors Lipoxygenase Inhibitors Peripheral Nervous System Agents Sensory System Agents UGT1A3 substrates
CAS number	156897-06-2

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Arachidonate 5-lipoxygenase	MPSYTVTVATGSQWFAGTDDYIYLSLVGSAGCSEKHLLDKPFYNDFERGA...	unknown
Prostaglandin G/H synthase 2	MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...	unknown
Group IIE secretory phospholipase A2	MKSPHVLVFLCLLVALVTGNLVQFGVMIEKMTGKSALQYNDYGCYCGIGG...	unknown
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	substrate,inhibitor
Cytochrome P450 2J2	MLAAMGSLAAALWAVVHPRTLLLGTVAFLLAADFLKRRRPKNYPPGPWRL...	unknown	substrate
UDP-glucuronosyltransferase 1-3	MATGLQVPLPWLATGLLLLLSVQPWAESGKVLVVPIDGSHWLSMREVLRE...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682