Lumiracoxib

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Structural formula
Structure of lumiracoxib
General
Non-proprietary name Lumiracoxib
other names

2 - [(2-chloro-6-fluoro-phenyl) amino] -5-methyl-phenylacetic acid ( IUPAC )

Molecular formula C 15 H 13 ClFNO 2
External identifiers / databases
CAS number 220991-20-8
PubChem 151166
ChemSpider 133236
DrugBank DB01283
Wikidata Q413744
Drug information
ATC code

M01 AH06

Drug class

Coxibs

properties
Molar mass 293.72 g · mol -1
Physical state

firmly

Melting point

158-159 ° C

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lumiracoxib is a drug from the group of cyclooxygenase-2 inhibitors (also called COX-2 inhibitors or coxibs) that was used to treat symptoms of activated osteoarthritis of the knee and hip. In contrast to the other selective COX-2 inhibitors, its structure is similar to that of diclofenac .

Lumiracoxib was approved in Germany in November 2006 in the form of tablets (Prexige ®  100 mg) according to a non-centralized EU procedure . In November 2007 the Federal Institute for Drugs and Medical Devices ordered the approval to be suspended. Finally, on March 28, 2008, the approval was completely revoked due to a decision by the European Commission.

Clinical information

Lumiracoxib 100 mg is used to treat symptoms of activated osteoarthritis of the knee and hip joints in patients aged 18 years and over. The dosage is 1 tablet (100 mg) once a day.

Pharmacological properties

The active ingredient is rapidly absorbed and has a relatively short plasma half-life of 4 to 6 hours, which means that lumiracoxib does not accumulate. The active ingredient is a carboxylic acid, which accumulates in the inflamed target tissue and can be detected there for 24 hours. This enables 24-hour therapy with a once-daily dosage.

Other Information

Chemical information

Lumiracoxib was derived from the non-selective COX inhibitor diclofenac , which is used as a standard therapeutic agent in the treatment of rheumatic diseases. Lumiracoxib is the only coxib so far without a sulfone or sulfonic acid amide structure. This means that allergic reactions that can be traced back to these structures cannot occur.

Withdrawal from the market

Lumiracoxib (100 mg, 200 mg and 400 mg tablets) has been withdrawn from the market in Australia due to reports of severe liver reactions. The Australian Therapeutic Goods Administration (TGA) had received eight reports of serious liver damage between March and August 2007, including two deaths and two liver transplants. New Zealand followed suit with the withdrawal of the 200 mg and 400 mg strengths. In Canada, too, lumiracoxib was withdrawn from the market in October 2007 due to cases of severe liver damage. The drug was not approved in the United States. The local drug authority FDA (Food and Drug Administration) refused approval in September 2007.

In mid-November 2007, the drug authorities in Germany and Great Britain ordered the suspension of approval until further notice, and sales in Austria were also discontinued. In December 2007, the European Medicines Agency recommended that the approval be withdrawn across the EU market.

study

  • Thomas J. Schnitzer, Gerd R. Burmester, Eduardo Mysler, Marc C. Hochberg, Michael Doherty, Elena Ehrsam, Xavier Gitton, Gerhard Krammer, Bernhard Mellein, Patrice Matchaba, Alberto Gimona, Christopher J. Hawkey: Comparison of lumiracoxib with naproxen and ibuprofen in the Therapeutic Arthritis Research and Gastrointestinal Event Trial (TARGET), reduction in ulcer complications: randomized controlled trial. In: The Lancet . Vol. 364, No. 9435, 2004, pp. 665-674, PMID 15325831 , doi: 10.1016 / S0140-6736 (04) 16893-1 .

Individual evidence

  1. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 971, ISBN 978-0-911910-00-1 .
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Lumiracoxib (Prexige®): The BfArM orders the approval to be suspended. BfArM , November 19, 2007, accessed on February 26, 2017 .
  4. ↑ Lumiracoxib (Prexige®): The BfArM orders the revocation of the approval. BfArM , March 28, 2008, archived from the original on February 26, 2017 ; accessed on February 26, 2017 .
  5. ↑ Lumiracoxib (Prexige®): Withdrawal from the Australian market due to severe liver damage. BfArM , August 14, 2007, archived from the original on February 27, 2017 ; accessed on February 26, 2017 .
  6. ↑ Medicines Regulator cancels registration of anti inflammatory drug, Lumiracoxib (Prexige) ( Memento from June 3, 2009 in the Internet Archive ).
  7. ↑ Prexige 200mg and 400mg tablets to be withdrawn in New Zealand. New Zealand Medicines and Medical Devices Safety Authority, August 21, 2007, accessed February 26, 2017 .
  8. ↑ European Medicines Agency recommends withdrawal of the marketing authorizations for lumiracoxib-containing medicines. EMEA , December 13, 2007, accessed February 26, 2017 .

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