Cerivastatin

Cerivastatin
Clinical data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • Withdrawn
Pharmacokinetic data
Elimination half-life2–3 hours
Identifiers
  • (3R,5S,6E)-7-[4-(4-Fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H34FNO5
Molar mass459.558 g·mol−1
3D model (JSmol)
  • O=C(O)C[C@H](O)C[C@H](O)/C=C/c1c(nc(c(c1c2ccc(F)cc2)COC)C(C)C)C(C)C
  • 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 checkY
  • Key:SEERZIQQUAZTOL-ANMDKAQQSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Cerivastatin (INN,[1] 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 Cerivastatin was voluntarily withdrawn from the market worldwide in 2001, due to reports of fatal rhabdomyolysis.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 postmarketing surveillance, 52 deaths were reported in patients using cerivastatin, mainly from rhabdomyolysis and its resultant kidney failure.[2] 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 a contraindication for the concomitant use of cerivastatin and gemfibrozil to the package 18 months after the drug interaction was found.[3] The frequency of deadly cases of rhabdomyolysis with cerivastatin was 16 to 80 times higher than with other statins.[4] 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in a dose-dependent manner when administered as monotherapy, but that was revealed only after Bayer was sued and unpublished company documents were opened.[5]

  1. ^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 36" (PDF). World Health Organization. 1996. p. 142. Retrieved 29 November 2016.
  2. ^ Furberg CD, Pitt B (2001). "Withdrawal of cerivastatin from the world market". Current Controlled Trials in Cardiovascular Medicine. 2 (5): 205–207. doi:10.1186/cvm-2-5-205. PMC 59524. PMID 11806796.
  3. ^ Psaty BM, Furberg CD, Ray WA, Weiss NS (December 2004). "Potential for conflict of interest in the evaluation of suspected adverse drug reactions: use of cerivastatin and risk of rhabdomyolysis". JAMA. 292 (21): 2622–2631. doi:10.1001/jama.292.21.2622. PMID 15572720.
  4. ^ Zeitlinger M, Müller M (2003). "[Clinico-pharmacologic explanation models of cerivastatin associated rhabdomyolysis]". Wiener Medizinische Wochenschrift (in German). 153 (11–12): 250–254. doi:10.1046/j.1563-258X.2003.03029.x. PMID 12879633. S2CID 38741903.
  5. ^ 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]". Kokuritsu Iyakuhin Shokuhin Eisei Kenkyujo Hokoku = Bulletin of National Institute of Health Sciences (in Japanese) (123): 41–45. PMID 16541751.