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220991-20-8 molecular structure
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2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid

ChemBase ID: 1141
Molecular Formular: C15H13ClFNO2
Molecular Mass: 293.7206232
Monoisotopic Mass: 293.06188456
SMILES and InChIs

SMILES:
Clc1c(Nc2c(cc(cc2)C)CC(=O)O)c(F)ccc1
Canonical SMILES:
OC(=O)Cc1cc(C)ccc1Nc1c(F)cccc1Cl
InChI:
InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20)
InChIKey:
KHPKQFYUPIUARC-UHFFFAOYSA-N

Cite this record

CBID:1141 http://www.chembase.cn/molecule-1141.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid
IUPAC Traditional name
lumiracoxib
Brand Name
Prexige (Novartis)
Prexige
Synonyms
lumiracoxib
COX 189
Lumiracoxib
2-[(2-Chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic Acid
2-[2-(2-Chloro-6-fluorophenylamino)-5-methylphenyl]acetic Acid
CGS 35189
Prexige
Lumiracoxib (COX-189)
CAS Number
220991-20-8
PubChem SID
46506378
160964604
PubChem CID
151166

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.114901  H Acceptors
H Donor LogD (pH = 5.5) 2.911556 
LogD (pH = 7.4) 1.2215736  Log P 4.311088 
Molar Refractivity 75.9142 cm3 Polarizability 28.60001 Å3
Polar Surface Area 49.33 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.56  LOG S -4.73 
Solubility (Water) 5.49e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Apperance
Pale Yellow Solid expand Show data source
Melting Point
139-141°C expand Show data source
Hydrophobicity(logP)
3.9 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Target
COX expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB01283 external link
Item Information
Drug Groups approved; investigational
Description Lumiracoxib is a COX-2 selective inhibitor non-steroidal anti-inflammatory drug. 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.
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.
Toxicity 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.
Affected Organisms
Humans and other mammals
Biotransformation 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.
Absorption Rapidly absorbed following oral administration, with an absolute oral bioavailablity of 74%.
Half Life Terminal half-life is approximately 4 hours.
Protein Binding Highly bound to plasma proteins (>= 98%).
External Links
Wikipedia
Toronto Research Chemicals - L474700 external link
Selective cyclooxygenase-2-(COX-2) inhibitor. Anti-inflammatory.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Bitner, M., et al.: Int. J. Clin. Pract., 58, 340 (2004)
  • • Packman, E., et al.: Headache, 45, 1163 (2004)
  • • Rordorf, C.M., et al.: Clin. Pharmacokinet., 44. 1247 (2004)
  • • Schnitzer, T.J., et al.: Curr. Med. Res. Opin., 21, 151 (2004)
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PATENTS

PATENTS

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INTERNET

INTERNET

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