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Licofelone

Licofelone structure

CAS No:
156897-06-2
Formula:
C23H22ClNO2
Chemical Name:
Licofelone
Synonyms:
1H-Pyrrolizine-5-acetic acid,6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-;6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-acetic acid;ML 3000;Licofelone;[2,2-Dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid
Categories:
Biochemical Engineering > Inhibitors

Description

Yellowish Solid

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.

Licofelone Basic Attributes

Molecular Weight：

379.88

Exact Mass：

379.88

EC Number：

1312995-182-4

UNII：

P5T6BYS22Y

DSSTox ID：

DTXSID40166154

Characteristics

PSA：

42.2

XLogP3：

6.73

Appearance：

Yellowish solid

Density：

1.23

Melting Point：

156-157 °C

Boiling Point：

539.7±50.0 °C(Predicted)

Flash Point：

280.2±30.1 °C

Refractive Index：

1.627

Storage Conditions：

-20°C Freezer

Vapor Pressure：

1.76E-12mmHg at 25°C

Safety Information

Precautionary statement(s)：

P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, P501

Hazard Statements：

H302

Drug Information

Drug Indication：

For the management of osteoarthritis.

Pharmacology：

Licofelone belongs to a novel class of dual-acting anti-inflammatory drugs called COX/LO inhibitors. This group of drugs simultaneously inhibits the enzymes cyclooxygenase (COX) and 5-lipoxygenase (LO).

MeSH：

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)|Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)|Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES. (See all compounds classified as Lipoxygenase Inhibitors.)|Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

Metabolism/Metabolites：

Licofelone has known human metabolites that include (2S,3S,4S,5R)-6-[2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid, Licofelone M2, and Licofelone M4.

Mechanism of Action：

Licofelone, through combined 5-LOX/COX-inhibition, reduces levels of inflammatory prostaglandins and leukotrienes.

MeSH Entry Terms：

(2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetic acid

Licofelone Use and Manufacturing

Dual inhibitor of cyclooxygenase and 5-lipoxygenase. Anti-inflammatory

Computed Properties

Molecular Weight:379.9
XLogP3:5.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:379.1339066
Monoisotopic Mass:379.1339066
Topological Polar Surface Area:42.2
Heavy Atom Count:27
Complexity:537
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 156897-06-2

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Licofelone

CAS No.: 156897-06-2

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