Rofekoksib

(IUPAC) ime

4-(4-metilsulfonilfenil)-3-fenil-5H-furan-2-on

Klinički podaci

Identifikatori

CAS broj

162011-90-7

ATC kod

M01AH02

PubChem^[1]^[2]

5090

DrugBank

APRD00151

ChemSpider^[3]

4911

UNII

0QTW8Z7MCR^Y

KEGG^[4]

D00568^Y

ChEBI

CHEBI:8887^Y

ChEMBL^[5]

CHEMBL122^Y

Hemijski podaci

Formula

C₁₇H₁₄O₄S

Mol. masa

314.357 g/mol

SMILES

eMolekuli & PubHem

InChI
InChI=1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3^Y Key: RZJQGNCSTQAWON-UHFFFAOYSA-N^Y

Farmakokinetički podaci

Bioraspoloživost

93%

Vezivanje za proteine plazme

87%

Metabolizam

hepatički

Poluvreme eliminacije

17 sati

Izlučivanje

bilijarno/renalno

Farmakoinformacioni podaci

Trudnoća

Pravni status

povučen sa tržišta

Način primene

oralno

Rofekoksib je nesteroidni antiinflamatorni lek (NSAID) koji je povučen sa tržišta iz bezbednostnih razloga. Njega je razvila kompanija Merk (Merck & Co.) za lečenje osteoartritisa, stanja akutnog bola i dismenoreja. Rofekoksib je FDA odobrila 20. maja 1999. On je bio u prodaji pod imenima Vioxx, Ceoxx, i Ceeoxx.

Rofekoksib je postao široko prihvaćen među lekarima koji su tretirali pacijente sa artritisom i drugim oboljenjima koja izazivaju hronični ili akutni bol. Svojevremeno je širom sveta ovaj lek je koristilo oko 80 miliona ljudi.^[6]

Merk je 30. septembra 2004 povukao rofekoksib sa tržišta usled zabrinutosti zbog povećanog rizika od srčanog udara vezanog za dugotrajnu upotrebu visokih doza leka. Do povlačenja je došlo nakon obelodanjivanja da informacije o rizicima nisu bile objavljene više od pet godina. To je uzrokovalo između 88,000 i 140,000 slučajeva ozbiljnih oboljenja srca.^[7] Rofekoksib je bio jedan od najšire korištenih lekova ikad povučenih sa tržišta. U toku godine pre povlačenja, Merkov prihod od prodaje Vajoksa je bio US$2.5 milijarde.^[8]

Rofekoksib je bio dostupan na recept, u obliku tableta i kao oralna suspenzija. U obliku injekcija je prodavan za bolničku upotrebu.

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ „Merck Pulls Arthritis Drug Vioxx from Market”.
↑ Slate (14. 11. 2011.). „The Cover-Up Artist”. Slate. str. 1.
↑ Reuters (07. 12. 2006.). „Merck Sees Slightly Higher 2007 Earnings”. New York Times. str. A1.

Literatura

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