Misplaced Pages

This is an old revision of this page, as edited by Beetstra (talk | contribs) at 20:59, 10 November 2011 (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'CAS_number').). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Cerivastatin

Clinical data
ATC code	C10AA06 (WHO)
Legal status
Legal status	Withdrawn from market
Pharmacokinetic data
Elimination half-life	2–3 hours
Identifiers
IUPAC name (3R,5S,6E)-7--3,5-dihydroxyhept-6-enoic acid
PubChem CID	446156
DrugBank	DB00439
ChemSpider	393588
UNII	AM91H2KS67
KEGG	D07661
ChEBI	CHEBI:3558
ChEMBL	ChEMBL1477
CompTox Dashboard (EPA)	DTXSID9022786
Chemical and physical data
Formula	C26H34FNO5
Molar mass	459.55 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(O)C(O)C(O)/C=C/c1c(nc(c(c1c2ccc(F)cc2)COC)C(C)C)C(C)C
InChI 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 Cerivastatin was voluntarily withdrawn from the market worldwide in 2001, due to reports of fatal rhabdomyolysis.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. 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. Frequency of deadly incidents of rhabdomyolysis with cerivastatin was 16 to 80 times higher than with other statins. 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in a dose-dependent manner when administrated as monotherapy, but that was revealed only after Bayer was sued and unpublished company documents were opened.

References

1. Furberg CD, Pitt B. Withdrawal of cerivastatin from the world market. Curr Control Trials Cardiovasc Med 2001;2:205-207. PMID 11806796.
2. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
3. Zeitlinger M, Müller M (2003). "". Wien Med Wochenschr (in German). 153 (11–12): 250–4. doi:10.1046/j.1563-258X.2003.03029.x. PMID 12879633.
4. Saito M, Hirata-Koizumi M, Miyake S, Hasegawa R (2005). "". Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku (in Japanese) (123): 41–5. PMID 16541751.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Further reading

• Alert: Voluntary withdrawal of Cerivastatin – Reports of Rhabdomyolysis. World Health Organization

• Pyridines
• Statins
• Withdrawn drugs
• Diols
• Carboxylic acids
• Organofluorides