羅非昔布

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羅非昔布

臨床資料
懷孕分級	澳: C
給藥途徑	oral
ATC碼	M01AH02 (WHO)
法律規範狀態
法律規範	澳：限醫生處方（S4） withdrawn
藥物動力學數據
生物利用度	93%
血漿蛋白結合率	87%
藥物代謝	hepatic
生物半衰期	17 hours
排泄途徑	biliary/renal
識別資訊
IUPAC命名法 4-(4-methylsulfonylphenyl)-3-phenyl-5H-furan-2-one
CAS號	162011-90-7  Y
PubChem CID	5090
DrugBank	DB00533 Y
ChemSpider	4911 Y
UNII	0QTW8Z7MCR
KEGG	D00568 Y
ChEBI	CHEBI:8887 Y
ChEMBL	ChEMBL122 Y
CompTox Dashboard (EPA)	DTXSID2023567
ECHA InfoCard	100.230.077
化學資訊
化學式	C17H14O4S
摩爾質量	314.357 g/mol
3D模型（JSmol）	交互式圖像
SMILES O=C2OCC(=C2\c1ccccc1)\c3ccc(cc3)S(=O)(=O)C
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

羅非昔布或羅非考昔（英語：Rofecoxib，/ˌrɒfɪˈkɒksɪb/）商品名Vioxx、Ceoxx和Ceeoxx。是一種非甾體類抗炎藥（NSAID），由默克公司製造、出售。美國食品藥品監督管理局（FDA）於1999年5月20日批准上市，用以治療骨關節炎、急性疼痛和痛經。

由於發現到長期且高劑量用藥有增加心臟病的風險，默克公司於2004年9月30日起從市場撤回此藥。

合成

羅非昔布的合成

參考文獻

• FDA (2005). "Summary minutes for the February 16, 17 and 18, 2005, Joint meeting of the Arthritis Advisory Committee and the Drug Safety and Risk Management Advisory Committee." Published on the internet, March 2005. Link （頁面存檔備份，存於網際網路檔案館）
• Fitzgerald GA, Coxibs and Cardiovascular Disease, N Engl J Med 2004;351(17): 1709–1711. PMID 15470192.
• Grassley CE (15 Oct 2004). Grassley questions Merck about communication with the FDA on Vioxx. Press Release.
• Jüni P, Nartey L, Reichenbach S, Sterchi R, Dieppe PA, Egger M (2004). Risk of cardiovascular events and rofecoxib: cumulative meta-analysis. Lancet (published online; see also Merck response below)
• Karha J and Topol EJ. The sad story of Vioxx, and what we should learn from it （頁面存檔備份，存於網際網路檔案館） Cleve Clin J Med 2004; 71(12):933-939. PMID 15641522
• Michaels, D. (June 2005) DOUBT Is Their Product Archive.is的存檔，存檔日期2006-03-21, Scientific American, 292 (6).
• Merck & Co., (5 Nov 2004). Response to Article by Juni et al. Published in The Lancet on Nov. 5. Press Release.
• Merck & Co (30 Sep 2004) Merck Announces Voluntary Worldwide Withdrawal of VIOXX. Press release [1].
• D. M. Mukherjee, S. E. Nissen, and E. J. Topol, "Risk of Cardiovascular Events Associated with Selective COX-2 Inhibitors," Journal of the American Medical Association 186 (2001): 954–959.
• Nussmeier NA, Whelton AA, Brown MT, Langford RM, Hoeft A, Parlow JL, et al. Complications of the COX-2 inhibitors parecoxib and valdecoxib after cardiac surgery. N Engl J Med 2005;352(11):1081-91. PMID 15713945
• Okie, S (2005) "Raising the safety bar--the FDA's coxib meeting." N Engl J Med. 2005 Mar 31;352(13):1283-5. PMID 15800221.
• Leleti Rajender Reddy, Corey EJ. Facile air oxidation of the conjugate base of rofecoxib (Vioxx), a possible contributor to chronic human toxicity Tetrahedron Lett 2005, 46: 927. doi:10.1016/j.tetlet.2004.12.055
• Swan SK et al., Effect of Cyclooxygenase-2 Inhibition on Renal Function in Elderly Persons Receiving a Low-Salt Diet. Annals of Int Med 2000; 133:1–9
• Targum, SL. (1 Feb. 2001) Review of cardiovascular safety database. FDA memorandum. [2] （頁面存檔備份，存於網際網路檔案館）
• Wolfe, MM et al., Gastrointestinal Toxicity of Nonsteroidal Anti-anflamattory Drugs, New England Journal of Medicine. 1999; 340; 1888-98.

外部連結

• National Public Radio 2004 Q&A on the case, following withdrawal announcement （頁面存檔備份，存於網際網路檔案館）
• Court TV's full coverage of the Vioxx civil trials
• Merck website on Vioxx litigation
• FDA Public Health Advisory on Vioxx （頁面存檔備份，存於網際網路檔案館）
• David Michaels. Doubt is Their Product Scientific American, June 2004, p. 96-101
• JURIST, Much Pain, Much Gain: Skeptical Ruminations on the Vioxx Litigation
• Ted Frank, American Enterprise Institute, The Vioxx Litigation, Part I and Part II, December 2005
• briandeer.com - Vioxx: the UK connection （頁面存檔備份，存於網際網路檔案館）
• Campaign for compensation for Vioxx victims outside the US