4'-Hydroxy-5-carboxy-lumiracoxib

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 4'-Hydroxy-5-carboxy-lumiracoxib are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 4'-Hydroxy-5-carboxy-lumiracoxib?

The molecule 4'-Hydroxy-5-carboxy-lumiracoxib presents a molecular formula of C16H13ClFNO5 and its IUPAC name is 3-[2-(carboxymethyl)-4-methylanilino]-4-chloro-2-fluoro-6-hydroxybenzoic acid.

Lumiracoxib (Prexige) is a nonsteroidal anti-inflammatory drug (NSAID) of the coxib class. It was withdrawn from the market in 2007 due to concerns about liver toxicity..

Lumiracoxib was developed by Beecham (now part of GlaxoSmithKline) and approved by the FDA in December 2004. It was marketed as a once-daily treatment for osteoarthritis and rheumatoid arthritis..

In September 2005, the FDA issued a public health advisory warning that lumiracoxib may be associated with an increased risk of liver injury. Beecham conducted a clinical trial of lumiracoxib in 2006, which showed an increased risk of liver injury compared to placebo..

In December 2006, Beecham announced that it was voluntarily withdrawing lumiracoxib from the market..

Lumiracoxib is a member of the coxib class of NSAIDs, which also includes celecoxib (Celebrex) and rofecoxib (Vioxx). Coxibs are more selective inhibitors of cyclooxygenase-2 (COX-2), an enzyme that participes in inflammation..

While coxibs are generally considered to be safer than traditional NSAIDs, they still carry a risk of gastrointestinal bleeding and other side effects. The increased risk of liver injury with lumiracoxib is thought to be due to its unique structure..

Lumiracoxib is metabolized by the liver to an active metabolite, 4'-hydroxy-5-carboxy-lumiracoxib. This metabolite is a potent inhibitor of COX-2..

In animal studies, 4'-hydroxy-5-carboxy-lumiracoxib has been shown to cause liver toxicity. It is thought that this metabolite is responsible for the liver injury seen in patients taking lumiracoxib..

If you have been taking lumiracoxib and have any liver problems, you should contact your doctor immediately. You should also be aware that the risk of liver injury may be increased in people who drink alcohol or have liver disease..

3D structure

Cartesian coordinates

Geometry of 4'-Hydroxy-5-carboxy-lumiracoxib in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

4'-Hydroxy-5-carboxy-lumiracoxib QQKNIFQTDAHPAP-UHFFFAOYSA-N chemical compound 2D structure molecule svg
4'-Hydroxy-5-carboxy-lumiracoxib

 

Molecule descriptors

 
IUPAC name3-[2-(carboxymethyl)-4-methylanilino]-4-chloro-2-fluoro-6-hydroxybenzoic acid
InChI codeInChI=1S/C16H13ClFNO5/c1-7-2-3-10(8(4-7)5-12(21)22)19-15-9(17)6-11(20)13(14(15)18)16(23)24/h2-4,6,19-20H,5H2,1H3,(H,21,22)(H,23,24)
InChI KeyQQKNIFQTDAHPAP-UHFFFAOYSA-N
SMILESCc1ccc(Nc2c(Cl)cc(O)c(C(=O)O)c2F)c(CC(=O)O)c1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 4'-Hydroxy-5-carboxy-lumiracoxib

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:

Physico-Chemical properties

IUPAC name3-[2-(carboxymethyl)-4-methylanilino]-4-chloro-2-fluoro-6-hydroxybenzoic acid
Molecular formulaC16H13ClFNO5
Molecular weight353.73
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity86.45
LogP3.6
Topological polar surface area106.9

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.