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Lumiracoxib

Lumiracoxib structure

CAS No:
220991-20-8
Formula:
C15H13ClFNO2
Chemical Name:
Lumiracoxib
Synonyms:
Benzeneacetic acid,2-[(2-chloro-6-fluorophenyl)amino]-5-methyl-;2-[(2-Chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid;COX 189;Lumiracoxib;Prexige;CGS 35189;2-[2-(2-Chloro-6-fluorophenylamino)-5-methylphenyl]acetic acid;[2-[(2-Chloro-6-fluorophenyl)amino]-5-methylphenyl]acetic acid;346670-74-4;697287-18-6
Categories:
Biochemical Engineering > Inhibitors

Description

Pale Yellow Solid

Solid

Lumiracoxib is an amino acid that is phenylacetic acid which is substituted at position 2 by the nitrogen of 2-chloro-6-fluoroaniline and at position 5 by a methyl group. A highly selective cyclooxygenase 2 inhibitor, it was briefly used for the treatment of osteoarthritis, but was withdrawn due to concersns of hepatotoxicity. It has a role as a cyclooxygenase 2 inhibitor and a non-steroidal anti-inflammatory drug. It is an organofluorine compound, an organochlorine compound, an amino acid, a secondary amino compound and a monocarboxylic acid.|Lumiracoxib is a COX-2 selective non-steroidal anti-inflammatory drug (NSAID). On August 11, 2007, Australia's Therapeutic Goods Administration (TGA, the Australian equivalent of the FDA) cancelled the registration of lumiracoxib in Australia due to concerns that it may cause liver failure. New Zealand and Canada have also followed suit in recalling the drug.

Lumiracoxib Basic Attributes

Molecular Weight：

293.724

Exact Mass：

293.72

EC Number：

1308068-626-2

UNII：

V91T9204HU

DSSTox ID：

DTXSID9049035

ATC Code：

M - Musculo-skeletal system

Characteristics

PSA：

49.3

XLogP3：

4.2

Appearance：

Pale Yellow Solid

Density：

1.4±0.1 g/cm3

Melting Point：

152-154 °C

Boiling Point：

395.7°C at 760 mmHg

Flash Point：

193.1±27.9 °C

Refractive Index：

1.628

Water Solubility：

5.49e-03 g/L

Storage Conditions：

-20°C Freezer

Vapor Pressure：

5.68E-07mmHg at 25°C

Toxicity

Toxicity Summary：

Single oral doses in mice and rats resulted in mortality and/or moribundity at doses of 600 mg/kg and 500 mg/kg, respectively. Single intraperitoneal doses in mice and rats results in mortality/moribundity at 750 mg/kg and 1000 mg/kg, respectively. The maximum non-lethal single oral and intraperitoneal dose in mouse was 300 mg/kg and 250 mg/kg, respectively. In the rat it was 150 mg/kg and 250 mg/kg, respectively.

Protein Binding：

Highly bound to plasma proteins (>= 98%).

Drug Information

Drug Indication：

For the acute and chronic treatment of the signs and symptoms of osteoarthritis of the knee in adults.

Pharmacology：

Lumiracoxib has a different structure from the standard COX-2 inhibitors (e.g. celecoxib). It more closely resembles the structure of diclofenac (one chlorine substituted by fluorine, the phenylacetic acid has another methyl group in meta position), making it a member of the arylalkanoic acid family of NSAIDs. It binds to a different site on the COX-2 receptor than the standard COX-2 inhibitors. It displays extremely high COX-2 selectivity.

MeSH：

A subclass of cyclooxygenase inhibitors with specificity for CYCLOOXYGENASE-2. (See all compounds classified as Cyclooxygenase 2 Inhibitors.)

Absorption：

Rapidly absorbed following oral administration, with an absolute oral bioavailablity of 74%.

Metabolism/Metabolites：

Hepatic oxidation and hydroxylation via CYP2C9. Three major metabolites have been identified in plasma: 4'-hydroxy-lumiracoxib, 5-carboxy-lumiracoxib, and 4'-hydroxy-5-carboxy-lumiracoxib.|Lumiracoxib has known human metabolites that include 4p-Carboxylumiracoxib, Lumiracoxib O-glucuronide, and Lumiracoxib metabolite 1.

Biological Half-Life：

Terminal half-life is approximately 4 hours.

Mechanism of Action：

The mechanism of action of lumiracoxib is due to inhibition of prostaglandin synthesis via inhibition of cyclooygenase-2 (COX-2). Lumiracoxib does not inhibit COX-1 at therapeutic concentrations.

MeSH Entry Terms：

COX 189

Lumiracoxib Use and Manufacturing

antiinflammatory, analgesic, antiarthritic

Computed Properties

Molecular Weight:293.72
XLogP3:4.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:293.0618845
Monoisotopic Mass:293.0618845
Topological Polar Surface Area:49.3
Heavy Atom Count:20
Complexity:342
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Lumiracoxib

CAS No.: 220991-20-8

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