- Cerivastatin
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Cerivastatin 
Systematic (IUPAC) name (3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid Clinical data Pregnancy cat. ? Legal status Withdrawn from market Pharmacokinetic data Half-life 2–3 hours Identifiers CAS number 145599-86-6 
ATC code C10AA06 PubChem CID 446156 DrugBank APRD00102 ChemSpider 393588 
UNII AM91H2KS67 KEGG D07661 ChEBI CHEBI:3558 ChEMBL CHEMBL1477 Chemical data Formula C26H34FNO5 Mol. mass 459.55 g/mol SMILES eMolecules & PubChem - InChI=1S/C26H34FNO5/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32)/b11-10+/t19-,20-/m1/s1
Key:SEERZIQQUAZTOL-ANMDKAQQSA-N
(what is this?) (verify)Cerivastatin (brand names: Baycol, Lipobay) is a synthetic member of the class of statins used to lower cholesterol and prevent cardiovascular disease. It was marketed by the pharmaceutical company Bayer A.G. in the late 1990s, competing with Pfizer's highly successful atorvastatin (Lipitor). Cerivastatin was voluntarily withdrawn from the market worldwide in 2001, due to reports of fatal rhabdomyolysis.
During post-marketing surveillance, 52 deaths were reported in patients using cerivastatin, mainly from rhabdomyolysis and its resultant renal failure.[1] Risks were higher in patients using fibrates, mainly gemfibrozil (Lopid), and in patients using the highest (0.8 mg/day) dose of cerivastatin. Bayer A.G. added contraindication about the concomitant use of cerivastatin and gemfibrozil to the package 18 months after the drug interaction was found.[2] Frequency of deadly incidents of rhabdomyolysis with cerivastatin was 16 to 80 times higher than with other statins.[3] Another 385 nonfatal cases of rhabdomyolysis were reported. This put the risk of this (rare) complication at 5-10 times that of the other statins. Cerivastatin also induced myopathy in a dose-dependent manner when administrated as monotherapy, but that was revealed only after Bayer was sued and unpublished company documents were opened.[4]
References
- ^ Furberg CD, Pitt B. Withdrawal of cerivastatin from the world market. Curr Control Trials Cardiovasc Med 2001;2:205-207. PMID 11806796.
- ^ Psaty BM, Furberg CD, Ray WA, Weiss NS (2004). "Potential for conflict of interest in the evaluation of suspected adverse drug reactions: use of cerivastatin and risk of rhabdomyolysis". JAMA 292 (21): 2622–31. doi:10.1001/jama.292.21.2622. PMID 15572720.
- ^ Zeitlinger M, Müller M (2003). "[Clinico-pharmacologic explanation models of cerivastatin associated rhabdomyolysis]" (in German). Wien Med Wochenschr 153 (11–12): 250–4. doi:10.1046/j.1563-258X.2003.03029.x. PMID 12879633.
- ^ Saito M, Hirata-Koizumi M, Miyake S, Hasegawa R (2005). "[Withdrawal of cerivastatin revealed a flaw of post-marketing surveillance system in the United States]" (in Japanese). Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku (123): 41–5. PMID 16541751.
Further reading
Lipid modifying agents (C10) GI tract Ezetimibe • SCH-48461Liver Simvastatin# • Atorvastatin • Fluvastatin • Lovastatin • Mevastatin • Pitavastatin • Pravastatin • Rosuvastatin • Cerivastatin‡Blood vessels CETP inhibitors (HDL)Combinations Other Dextrothyroxine • Probucol • Tiadenol • Benfluorex • Meglutol • Omega-3-triglycerides • Magnesium pyridoxal 5-phosphate glutamate • Policosanol • Lapaquistat§ • Alipogene tiparvovecCategories:- Pyridines
- Statins
- Withdrawn drugs
- Diols
- Carboxylic acids
- Organofluorides
- InChI=1S/C26H34FNO5/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32)/b11-10+/t19-,20-/m1/s1
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