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cerivastatin

Structure via PubChem · Public domain (PubChem)

EntityQ423439· pop 20· linked from 108 articles

cerivastatin

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Also known as Baycol®, Lipobay®, cerivastatin acid, (3R,5S,6E)-7-(4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl)-3,5-dihydroxy-6-heptenoic acid, (3R,5S,6E)-7-(4-(p-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridyl)-3,5-dihydroxy-6-heptenoic acid

Cerivastatin (INN, 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 Cerivastatin was voluntarily withdrawn from the market worldwide in 2001, due to reports of fatal rhabdomyolysis.

Chemical data

Formula
C26H34FNO5
Molecular weight
459.5 g/mol
IUPAC name
(E,3R,5S)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)-3-pyridinyl]-3,5-dihydroxyhept-6-enoic acid
SMILES
CC(C)C1=C(C(=C(C(=N1)C(C)C)COC)C2=CC=C(C=C2)F)/C=C/[C@H](C[C@H](CC(=O)O)O)O
InChIKey
SEERZIQQUAZTOL-ANMDKAQQSA-N
XLogP
3.6
Polar surface area
99.9 Ų
H-bond donors
3
H-bond acceptors
7
Formal charge
0

via PubChem

Research

820 papers

via PubMed

Wikidata facts

Subclass of
carboxylic acid
Mass
459.242101
Has use
medication
Show 10 more facts
chemical formula
C₂₆H₃₄FNO₅
medical condition treated
arteriosclerosis
World Health Organisation international non-proprietary name
cerivastatin
canonical SMILES
CC(C)C1=C(C(=C(C(=N1)C(C)C)C=CC(CC(CC(=O)O)O)O)C2=CC=C(C=C2)F)COC
Commons category
Cerivastatin
defined daily dose
0.2
isomeric SMILES
COCC1=C(C2=CC=C(F)C=C2)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C(N=C1C(C)C)C(C)C
NCI Thesaurus ID
C65308
subject has role
statin
physically interacts with
3-hydroxy-3-methylglutaryl-CoA reductase
Sources (4)

via Wikidata · CC0

~8 min read

Encyclopedic overview

7 sections
Contents
  • Structure and reactivity
  • Mechanism of action
  • Metabolism
  • Efficacy, toxicity and side effects
  • Efficacy and toxicity
  • Adverse effects
  • References

Cerivastatin (INN, 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. 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. The frequency of deadly cases 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 administered as monotherapy, but that was revealed only after Bayer was sued and unpublished company documents were opened.

Excerpted from Wikipedia’s “cerivastatin” article, available under the CC BY-SA 4.0 licence.

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