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<small>'''''Synonyms / Brand Names:''''' Cerivastatin sodium; Cerivastatin, sodium salt; Baycol; Lipobay, Rivastatin </small>
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 460025724
| IUPAC_name = (3''R'',5''S'',6''E'')-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
| image = Cerivastatin2DCSD.png
| width = 180px


{{CMG}}
<!--Clinical data-->
| tradename = 
| pregnancy_AU = D
| legal_status = Withdrawn from market
| routes_of_administration =


==Dosing and Administration==
<!--Pharmacokinetic data-->
The starting-dose of BAYCOL® is 0.4 mg once daily in the evening regardless of previous lipid therapy.  Since the maximal effect of cerivastatin sodium is seen within 4 weeks lipid determinations should be performed at this time and the dose adjusted based upon patient response. Only patients requiring further lipid adjustment should be titrated to 0.8 mg. The dosage range is 0.2 mg to 0.8 mg. In patients with significant renal impairment (creatinine clearance ≤60 mL/min/1.73m2 ) lower doses are recommended. Cerivastatin sodium may be taken with or without food.
| bioavailability =
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| metabolism =
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| elimination_half-life = 2–3 hours
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[[{{PAGENAME}}#FDA Package Insert Resources|FDA Package Insert Resources]]
<br></font size><small>Indications, Contraindications, Side Effects, Drug Interactions, etc.</small><font size="4"><br>
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[http://www.pace-med-apps.com/gfrcalc.htm Calculate Creatine Clearance]
<br></font size><small>On line calculator of your patients Cr Cl by a variety of formulas.</small><font size="4"><br>
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[http://home.earthlink.net/~sensei11/convert.htm Convert pounds to Kilograms]
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<br> [[{{PAGENAME}}#Publication Resources|Publication Resources]]
<br></font size><small>Recent articles, WikiDoc State of the Art Review, Textbook Information</small><font size="4"><br>
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[[{{PAGENAME}}#Trial Resources|Trial Resources]]
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[[{{PAGENAME}}#International Resources|International Resources]]
<br></font size><small>en Español</small><font size="4"><br>
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==FDA Package Insert Resources==
<!--Identifiers-->
[[{{PAGENAME}} indications|Indications]]
| CAS_number_Ref = {{cascite|changed|??}}
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| CAS_number = 145599-86-6
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| ATC_prefix = C10
[[{{PAGENAME}} contraindications|Contraindications]]
| ATC_suffix = AA06
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| ATC_supplemental = 
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| PubChem = 446156
[[{{PAGENAME}} side effects|Side Effects]]
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| DrugBank = DB00439
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
[[{{PAGENAME}} drug interactions|Drug Interactions]]
| ChemSpiderID = 393588
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| UNII_Ref = {{fdacite|correct|FDA}}
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| UNII = AM91H2KS67
[[{{PAGENAME}} precautions|Precautions]]
| KEGG_Ref = {{keggcite|correct|kegg}}
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| KEGG = D07661
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| ChEBI_Ref = {{ebicite|correct|EBI}}
[[{{PAGENAME}} overdose|Overdose]]
| ChEBI = 3558
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
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| ChEMBL = 1477
[[{{PAGENAME}} instructions for administration|Instructions for Administration]]
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[[{{PAGENAME}} how supplied|How Supplied]]
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[[{{PAGENAME}} pharmacokinetics and molecular data|Pharmacokinetics and Molecular Data]]
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[http://www.fda.gov/cder/foi/label/2001/20740s19lbl.pdf FDA label]
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[http://google2.fda.gov/search?q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&x=0&y=0&client=FDA&site=FDA&lr=&proxystylesheet=FDA&output=xml_no_dtd&getfields=* FDA on {{PAGENAME}}]
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==Publication Resources==
<!--Chemical data-->
[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?CMD=search&db=pubmed&term={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}} Most Recent Articles on {{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}]
| C=26 | H=34 | F=1 | N=1 | O=5
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| molecular_weight = 459.55 g/mol
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| 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
[http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=search&db=pubmed&term={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}%20AND%20systematic%5Bsb%5D  Review Articles on {{PAGENAME}}]
| InChI = 1/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
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| InChIKey = SEERZIQQUAZTOL-ANMDKAQQBT
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=search&db=pubmed&term={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}+AND+%28%28N+Engl+J+Med%5Bta%5D%29+OR+%28Lancet%5Bta%5D%29+OR+%28BMJ%5Bta%5D%29%29 Articles on {{PAGENAME}} in N Eng J Med, Lancet, BMJ]
| StdInChI = 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
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey = SEERZIQQUAZTOL-ANMDKAQQSA-N
[[Cerivastatin detailed information|WikiDoc State of the Art Review]]
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[http://books.google.com/books?ie=UTF-8&oe=utf-8&q={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&qt_s=Search&sa=N&tab=gp Textbook Information on {{PAGENAME}}]
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==Trial Resources==
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==Guidelines & Evidence Based Medicine Resources==
'''Cerivastatin''' (brand names: '''Baycol''', '''Lipobay''') is a synthetic member of the class of [[statin]]s used to lower [[cholesterol]] and prevent [[cardiovascular disease]]. It was marketed by the [[pharmaceutical company]] [[Bayer|Bayer A.G.]] in the late 1990s, competing with [[Pfizer Inc.|Pfizer]]'s highly successful [[atorvastatin]] (Lipitor). Cerivastatin was voluntarily withdrawn from the market worldwide in 2001, due to reports of fatal [[rhabdomyolysis]].
[http://www.guideline.gov/search/searchresults.aspx?Type=3&txtSearch={{urlencode:{{#if:{{{1|}}}|{{{1}}}|{{PAGENAME}}}}}}&num=20 US National Guidelines Clearinghouse on {{PAGENAME}}]
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==Patient Resources==
During [[postmarketing surveillance]], 52 deaths were reported in patients using cerivastatin, mainly from rhabdomyolysis and its resultant [[renal failure]].<ref>Furberg CD, Pitt B. Withdrawal of cerivastatin from the world market. Curr Control Trials Cardiovasc Med 2001;2:205-207. PMID 11806796.</ref> Risks were higher in patients using [[fibrate]]s, mainly [[gemfibrozil]] (Lopid), and in patients using the highest (0.8&nbsp;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.<ref name="pmid15572720">{{cite journal |author=Psaty BM, Furberg CD, Ray WA, Weiss NS |title=Potential for conflict of interest in the evaluation of suspected adverse drug reactions: use of cerivastatin and risk of rhabdomyolysis |journal=JAMA |volume=292 |issue=21 |pages=2622–31 |year=2004 |pmid=15572720 |doi=10.1001/jama.292.21.2622}}</ref> The frequency of deadly cases of [[rhabdomyolysis]] with cerivastatin was 16 to 80 times higher than with other statins.<ref name="pmid12879633">{{cite journal |author=Zeitlinger M, Müller M |title=[Clinico-pharmacologic explanation models of cerivastatin associated rhabdomyolysis] |language=German |journal=Wien Med Wochenschr |volume=153 |issue=11–12 |pages=250–4 |year=2003 |pmid=12879633 |doi=10.1046/j.1563-258X.2003.03029.x}}</ref> Another 385 nonfatal cases of [[rhabdomyolysis]] were reported. This put the risk of this (rare) complication at 5-10 times that of the other [[statin]]s. 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.<ref name="pmid16541751">{{cite journal |author=Saito M, Hirata-Koizumi M, Miyake S, Hasegawa R |title=[Withdrawal of cerivastatin revealed a flaw of post-marketing surveillance system in the United States] |language=Japanese |journal=Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku |volume= |issue=123 |pages=41–5 |year=2005 |pmid=16541751 |doi=}}</ref>
[[{{PAGENAME}} (patient information)|Patient Information from National Library of Medicine]]
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==International Resources==
==References==
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{{FDA}}


[[Category:Drugs]]
{{Statins}}
[[Category:Pyridines]]
[[Category:Statins]]
[[Category:Withdrawn drugs]]
[[Category:Diols]]
[[Category:Carboxylic acids]]
[[Category:Organofluorides]]
[[Category:Ethers]]
[[Category:Cardiovascular Drugs]][[Category:Drugs]]

Revision as of 20:53, 23 July 2014

Cerivastatin
Clinical data
Pregnancy
category
  • AU: D
ATC code
Legal status
Legal status
  • Withdrawn from market
Pharmacokinetic data
Elimination half-life2–3 hours
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
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
FormulaC26H34FNO5
Molar mass459.55 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]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

  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.
  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.
  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.

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