Cerivastatin

Cerivastatin
Clinical data
Pregnancy; category	AU: D ; ;
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Legal status	Withdrawn from market;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-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid;
CAS Number	145599-86-6 ;
PubChem CID	446156;
DrugBank	DB00439 ;
ChemSpider	393588 ;
UNII	AM91H2KS67;
KEGG	D07661 ;
ChEBI	CHEBI:3558 ;
ChEMBL	ChEMBL1477 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C26H34FNO5
Molar mass	459.55 g/mol
3D model (JSmol)	Interactive image;
	SMILES 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 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 ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1] Associate Editor(s)-in-Chief: Sheng Shi, M.D. [2]

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 Cerivastatin was voluntarily withdrawn from the market worldwide in 2001, due to reports of fatal rhabdomyolysis.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 postmarketing 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 a contraindication for the concomitant use of cerivastatin and gemfibrozil to the package 18 months after the drug interaction was found.^[2] The frequency of deadly cases 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 administered 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]". Wien Med Wochenschr (in German). 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]". Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku (in Japanese) (123): 41–5. PMID 16541751.

Template:Statins

[1] Furberg CD, Pitt B. Withdrawal of cerivastatin from the world market. Curr Control Trials Cardiovasc Med 2001;2:205-207. PMID 11806796.

[pmid15572720-2] 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.

[pmid12879633-3] Zeitlinger M, Müller M (2003). "[Clinico-pharmacologic explanation models of cerivastatin associated rhabdomyolysis]". Wien Med Wochenschr (in German). 153 (11–12): 250–4. doi:10.1046/j.1563-258X.2003.03029.x. PMID 12879633.

[pmid16541751-4] 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 Kenkyusho Hokoku (in Japanese) (123): 41–5. PMID 16541751.

[1]

[2]

[3]

[4]

Clinical data

Pregnancy category	AU: D
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-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
CAS Number	145599-86-6^N
PubChem CID	446156
DrugBank	DB00439^Y
ChemSpider	393588^Y
UNII	AM91H2KS67
KEGG	D07661^Y
ChEBI	CHEBI:3558^Y
ChEMBL	ChEMBL1477^Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₆H₃₄FNO₅
Molar mass	459.55 g/mol
3D model (JSmol)	Interactive image
SMILES 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 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^Y Key:SEERZIQQUAZTOL-ANMDKAQQSA-N^Y
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Cerivastatin

References

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