羅非昔布

羅非昔布或羅非考昔（Rofecoxib，ˌ）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

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## 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
- Fitzgerald GA, Coxibs and Cardiovascular Disease, N Engl J Med 2004;351(17): 1709–1711. .
- 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 Cleve Clin J Med 2004; 71(12):933-939.
- Michaels, D. (June 2005) DOUBT Is Their Product , 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 .
- 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.
- Okie, S (2005) "Raising the safety bar--the FDA's coxib meeting." N Engl J Med. 2005 Mar 31;352(13):1283-5. .
- 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. 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.
- 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
- Court TV's full coverage of the Vioxx civil trials
- Merck website on Vioxx litigation
- FDA Public Health Advisory on Vioxx
- 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
- Campaign for compensation for Vioxx victims outside the US

## 基本資料

- verifiedrevid：470623576
- IUPAC_name：4-(4-methylsulfonylphenyl)-3-phenyl-5H-furan-2-one
- pregnancy_AU：C
- 合法狀態：S4
- 狀態：亦被撤回
- 給藥途徑：口服
- 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
- CAS號：162011-90-7
- ATC碼：M01
- ATC碼：AH02
- PubChem：5090
- 藥物銀行資料庫：DB00533
- ChemSpiderID：4911
- UNII：0QTW8Z7MCR
- KEGG：D00568
- ChEBI：8887
- ChEMBL：122
- C：17
- H：14
- O：4
- 硫化物（SO）：1
- 3D模型（JSmol）：O=C2OCC(=C2\c1ccccc1)\c3ccc(cc3)S(=O)(=O)C
- InChI：1/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
- InChIKey：RZJQGNCSTQAWON-UHFFFAOYAR
- StdInChI：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
- StdInChIKey：RZJQGNCSTQAWON-UHFFFAOYSA-N