Cerivastatin

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Structural formula
Structure of cerivastatin
General
Non-proprietary name Cerivastatin
other names

(3 R , 5 S , 6 E ) -7- [4- (4-fluorophenyl) -5- (methoxymethyl) -2,6-bis (1-methylethyl) -3-pyridinyl] -3,5-dihydroxy- hept-6-enoic acid ( IUPAC )

Molecular formula C 26 H 34 FNO 5
External identifiers / databases
CAS number
PubChem 446156
ChemSpider 393588
DrugBank DB00439
Wikidata Q423439
Drug information
ATC code

C10 AA06

Drug class

Statins

Mechanism of action

HMG-CoA reductase - inhibitor

properties
Molar mass 459.55 g · mol -1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cerivastatin is a drug selected from the group of statins , which for lowering elevated blood fat levels was employed. Cerivastatin was developed in Japan and was marketed in Germany by Bayer (trade name: Lipobay ) and Fournier (trade name: Zenas ). In the United States, Bayer has sold cerivastatin as Baycol .

The drug was withdrawn from the market worldwide by Bayer in August 2001 after numerous deaths became known after its ingestion. The active ingredient cerivastatin, a substance from the pharmacotherapeutic class of cholesterol synthesis enzyme (CSE) inhibitors (also called statin or HMG-CoA reductase inhibitors), had in combination with gemfibrozil (e.g. in Gevilon ), a Also lipid-lowering preparation, led to the destruction of muscle tissue ( rhabdomyolysis ) and the resulting kidney failure . In addition to the common breakdown mechanism (CYP 2C8) of cerivastatin and fibrates, an inhibition of the uptake transporter OATP 2 is assumed to be the cause .

timeline

  • 1997: Drug approval in Germany and other European countries under the aegis of the British authority
  • July 1997: Approval in the USA
  • November 1998: The first death in Germany is reported to the Federal Institute for Drugs and Medical Devices (BfArM).
  • January 2000: the first death is known in the USA.
  • March 2001: The BfArM receives further reports of deaths.
  • June 2001: the BfArM requests Bayer to change the package insert. Bayer changes it to the effect that taking Lipobay and Gemfibrozil at the same time is contraindicated and informs the doctors about this in a red-hand letter .
  • August 8, 2001: Bayer takes Lipobay / Baycol off the market in Europe and the USA. The ad-hoc campaign arouses great resentment in specialist circles, as the press and shareholders were informed a few hours before doctors and pharmacists, who were initially perplexed by the insecure patients, for reasons of stock corporation law.
  • August 14, 2001: First lawsuits filed against Bayer in the United States, including by Ed Fagan for New Jersey residents .
  • August 23, 2001: Bayer also takes Lipobay / Baycol off the market in Japan
  • September 4, 2001: the Cologne Public Prosecutor's Office initiates an investigation against Bayer employees.
  • September 13, 2001: the BfArM withdraws the accusation that Bayer withheld information about the safety of Lipobay.
  • October 2005: Bayer pays USD 1.143 billion and thus achieves a settlement with 3,058 Baycol victims, that is an average of USD 373,733 per claim.
  • August 22, 2012: Bayer is sentenced in Argentina to pay 968,000 pesos (around 160,000 euros) to a Lipobay victim. The plaintiff, Flavio Rein, had suffered irreversible muscle damage ( rhabdomyolysis ), visual disturbances and kidney damage after taking the cholesterol-lowering drug for one month .
  • January 2013: Bayer is sentenced by a court in Venice to compensation of 350,000 euros to a Lipobay victim. A doctor, who was 51 at the time, prescribed the preparation himself in 1999. Two months later, he suffered life-threatening rhabdomyolysis (muscle breakdown) and was 100% unable to work. He has been receiving a disability pension since then. BAYER also has to bear the procedural costs of 14,000 euros.

Web links

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ^ Furberg CD, Pitt B: Withdrawal of cerivastatin from the world market . In: Curr Control Trials Cardiovasc Med . 2, No. 5, 2001, pp. 205-207. PMID 11806796 . PMC 59524 (free full text).
  3. ↑ Shitara Y, Hirano M, Sato H, Sugiyama Y .: Gemfibrozil and its glucuronide inhibit the organic anion transporting polypeptide 2 (OATP2 / OATP1B1: SLC21A6) -mediated hepatic uptake and CYP2C8-mediated metabolism of cerivastatin: analysis of the mechanism of the clinically relevant drug-drug interaction between cerivastatin and gemfibrozil. . In: J Pharmacol Exp Ther . 311, 2004. PMID 15194707 .
  4. ↑ Argentina: BAYER sentenced to compensation , accessed on April 11, 2019
  5. ↑ Argentina: BAYER sentenced to compensation , accessed on April 11, 2019
  6. ↑ BAYER sentenced to compensation in Italy