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MedKoo Cat#: 326866 | Name: Cerivastatin Sodium
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cerivastatin, also known as BAY-w-6228, and Rivastatin, is a statins used to lower cholesterol and prevent cardiovascular disease. It was marketed by the pharmaceutical company Bayer A.G. in the late 1990s. Cerivastatin was voluntarily withdrawn from the market worldwide in 2001, due to reports of fatal rhabdomyolysis.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.

Chemical Structure

Cerivastatin Sodium
CAS#143201-11-0 (sodium)

Theoretical Analysis

MedKoo Cat#: 326866

Name: Cerivastatin Sodium

CAS#: 143201-11-0 (sodium)

Chemical Formula: C26H33FNNaO5

Exact Mass: 841.2200

Molecular Weight: 481.54

Elemental Analysis: C, 64.85; H, 6.91; F, 3.95; N, 2.91; Na, 4.77; O, 16.61

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 625.00 2 Weeks
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Related CAS #
143201-11-0 (sodium) 145599-86-6 (free acid)
Synonym
BAY-w-6228; BAY-w 6228; BAY-w6228; Cerivastatin Sodium; Rivastatin; Lipobay
IUPAC/Chemical Name
sodium (3R,5S,E)-7-(4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl)-3,5-dihydroxyhept-6-enoate
InChi Key
GPUADMRJQVPIAS-QCVDVZFFSA-M
InChi Code
InChI=1S/C26H34FNO5.Na/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);/q;+1/p-1/b11-10+;/t19-,20-;/m1./s1
SMILES Code
O=C([O-])C[C@H](O)C[C@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C(COC)=C(C(C)C)N=C1C(C)C.[Na+]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO (5mg/mL)
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related CAS# CAS No. 145599-86-6 (Cerivastatin ) 143201-11-0 (Cerivastatin Sodium)
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot# C21M11C09
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Cerivastatin sodium is a synthetic lipid-lowering agent and a highly potent, well-tolerated and orally active HMG-CoA reductase inhibitor, with a Ki of 1.3 nM/L.
In vitro activity:
In this study, the mechanisms by which statins inhibit cancer and the types of cancers which could benefit from this therapy are investigated. In MDA-MB-231 cells, an aggressive breast cancer cell line with spontaneous activation of Ras and NFkappaB and overexpression of RhoA, cerivastatin induced inhibition of both cell proliferation and invasion through Matrigel. This anti-proliferative effect was related to G(1)/S arrest due to an increase in p21(Waf1/Cip1). The anti-invasive effect was observed from 18 h and could be explained by RhoA delocalization from the cell membrane, resulting in disorganization of the actin fibers and disappearance of focal adhesion sites. The importance of RhoA inactivation in both these inhibitory effects was proved by their reversion by GGPP but not by FPP. Moreover, cerivastatin was also shown to induce inactivation of NFkappaB, in a RhoA inhibition-dependent manner, resulting in a decrease in urokinase and metalloproteinase-9 expression, two proteases involved in cell migration. The participation of Ras inactivation is considered a subsidiary mechanism for the effects of cerivastatin, as they were not rescued by FPP. Prolonged treatment of MDA-MB-231 cells with high doses of cerivastatin induced a loss of cell attachment. Interestingly, the effect of cerivastatin was considerably lower on poorly invasive MCF-7 cells. In conclusion, our results suggest that cerivastatin inhibits cell signaling pathways involved in the invasiveness and metastatic properties of highly invasive cancers. Reference: Carcinogenesis. 2001 Aug;22(8):1139-48. https://academic.oup.com/carcin/article-lookup/doi/10.1093/carcin/22.8.1139
In vivo activity:
Administration of cerivastatin improved significantly the survival rate of mice challenged with LPS (31% vs. 19% in the PBS group; p = 0.001), S. aureus (56% vs. 20% in PBS group; p = 0.01), or S. typhimurium (48% vs. 10% in PBS group; p = 0.03). Significantly reduced release of the pro-inflammatory cytokines tumor necrosis factor (TNF)-alpha and interleukin (IL)-6 was evident in cerivastatin-treated mice after LPS challenge. Cerivastatin-treated mice showed insignificant reductions in serum TNF-alpha and IL-6 concentrations after bacterial challenge. However, significantly accelerated bacterial clearance was demonstrated in cerivastatin-treated mice 24 h after S. typhimurium infection and 48 h after S. aureus infection. Reference: Surg Infect (Larchmt). 2008 Apr;9(2):183-94. https://www.liebertpub.com/doi/10.1089/sur.2006.077?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%20%200pubmed
Solvent mg/mL mM comments
Solubility
Water 125.0 259.59
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 481.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Denoyelle C, Vasse M, Körner M, Mishal Z, Ganné F, Vannier JP, Soria J, Soria C. Cerivastatin, an inhibitor of HMG-CoA reductase, inhibits the signaling pathways involved in the invasiveness and metastatic properties of highly invasive breast cancer cell lines: an in vitro study. Carcinogenesis. 2001 Aug;22(8):1139-48. doi: 10.1093/carcin/22.8.1139. PMID: 11470741.
In vivo protocol:
1. Chaudhry MZ, Wang JH, Blankson S, Redmond HP. Statin (cerivastatin) protects mice against sepsis-related death via reduced proinflammatory cytokines and enhanced bacterial clearance. Surg Infect (Larchmt). 2008 Apr;9(2):183-94. doi: 10.1089/sur.2006.077. PMID: 18426351. 2. Stein E, Sprecher D, Allenby KS, Tosiello RL, Whalen E, Ripa SR. Cerivastatin, a New Potent Synthetic HMG Co-A Reductase Inhibitor: Effect of 0.2 mg Daily in Subjects With Primary Hypercholesterolemia. J Cardiovasc Pharmacol Ther. 1997 Jan;2(1):7-16. doi: 10.1177/107424849700200102. PMID: 10684437.
1: Mezquita B, Mezquita P, Pau M, Gasa L, Navarro L, Samitier M, Pons M, Mezquita C. All-trans-retinoic acid activates the pro-invasive Src-YAP-Interleukin 6 axis in triple-negative MDA-MB-231 breast cancer cells while cerivastatin reverses this action. Sci Rep. 2018 May 4;8(1):7047. doi: 10.1038/s41598-018-25526-1. PubMed PMID: 29728589; PubMed Central PMCID: PMC5935706. 2: Yao Y, Toshimoto K, Kim SJ, Yoshikado T, Sugiyama Y. Quantitative Analysis of Complex Drug-Drug Interactions between Cerivastatin and Metabolism/Transport Inhibitors Using Physiologically Based Pharmacokinetic Modeling. Drug Metab Dispos. 2018 Jul;46(7):924-933. doi: 10.1124/dmd.117.079210. Epub 2018 Apr 30. PubMed PMID: 29712725. 3: Lee Y, Pai SB, Bellamkonda RV, Thompson DH, Singh J. Cerivastatin Nanoliposome as a Potential Disease Modifying Approach for the Treatment of Pulmonary Arterial Hypertension. J Pharmacol Exp Ther. 2018 Jul;366(1):66-74. doi: 10.1124/jpet.118.247643. Epub 2018 Apr 25. PubMed PMID: 29695410; PubMed Central PMCID: PMC5987999. 4: Gaukler SM, Ruff JS, Galland T, Underwood TK, Kandaris KA, Liu NM, Morrison LC, Veranth JM, Potts WK. Quantification of cerivastatin toxicity supports organismal performance assays as an effective tool during pharmaceutical safety assessment. Evol Appl. 2016 Apr 15;9(5):685-96. doi: 10.1111/eva.12365. eCollection 2016 Jun. PubMed PMID: 27247619; PubMed Central PMCID: PMC4869410. 5: Zhao J, Natarajan SK, Chronos N, Singh JP. Cerivastatin represses atherogenic gene expression through the induction of KLF2 via isoprenoid metabolic pathways. Cell Mol Biol Lett. 2015 Dec;20(5):825-39. doi: 10.1515/cmble-2015-0049. PubMed PMID: 26556845. 6: Tamraz B, Fukushima H, Wolfe AR, Kaspera R, Totah RA, Floyd JS, Ma B, Chu C, Marciante KD, Heckbert SR, Psaty BM, Kroetz DL, Kwok PY. OATP1B1-related drug-drug and drug-gene interactions as potential risk factors for cerivastatin-induced rhabdomyolysis. Pharmacogenet Genomics. 2013 Jul;23(7):355-64. doi: 10.1097/FPC.0b013e3283620c3b. PubMed PMID: 23652407; PubMed Central PMCID: PMC3894639. 7: Fuhrmeister J, Tews M, Kromer A, Moosmann B. Prooxidative toxicity and selenoprotein suppression by cerivastatin in muscle cells. Toxicol Lett. 2012 Dec 17;215(3):219-27. doi: 10.1016/j.toxlet.2012.10.010. Epub 2012 Oct 22. PubMed PMID: 23092657. 8: Floyd JS, Kaspera R, Marciante KD, Weiss NS, Heckbert SR, Lumley T, Wiggins KL, Tamraz B, Kwok PY, Totah RA, Psaty BM. A screening study of drug-drug interactions in cerivastatin users: an adverse effect of clopidogrel. Clin Pharmacol Ther. 2012 May;91(5):896-904. doi: 10.1038/clpt.2011.295. Epub 2012 Mar 14. PubMed PMID: 22419147; PubMed Central PMCID: PMC3830936. 9: Maxeiner H, Abdallah Y, Kuhlmann CR, Schlüter KD, Wenzel S. Effects of cerivastatin on adrenergic pathways, hypertrophic growth and TGFbeta expression in adult ventricular cardiomyocytes. Eur J Cell Biol. 2012 May;91(5):367-74. doi: 10.1016/j.ejcb.2011.12.006. Epub 2012 Feb 23. PubMed PMID: 22365145. 10: Obayashi H, Nezu Y, Yokota H, Kiyosawa N, Mori K, Maeda N, Tani Y, Manabe S, Sanbuissho A. Cerivastatin induces type-I fiber-, not type-II fiber-, predominant muscular toxicity in the young male F344 rats. J Toxicol Sci. 2011 Aug;36(4):445-52. PubMed PMID: 21804308. 11: Marciante KD, Durda JP, Heckbert SR, Lumley T, Rice K, McKnight B, Totah RA, Tamraz B, Kroetz DL, Fukushima H, Kaspera R, Bis JC, Glazer NL, Li G, Austin TR, Taylor KD, Rotter JI, Jaquish CE, Kwok PY, Tracy RP, Psaty BM. Cerivastatin, genetic variants, and the risk of rhabdomyolysis. Pharmacogenet Genomics. 2011 May;21(5):280-8. doi: 10.1097/FPC.0b013e328343dd7d. PubMed PMID: 21386754; PubMed Central PMCID: PMC3076530. 12: Kaspera R, Naraharisetti SB, Tamraz B, Sahele T, Cheesman MJ, Kwok PY, Marciante K, Heckbert SR, Psaty BM, Totah RA. Cerivastatin in vitro metabolism by CYP2C8 variants found in patients experiencing rhabdomyolysis. Pharmacogenet Genomics. 2010 Oct;20(10):619-29. doi: 10.1097/FPC.0b013e32833ecace. PubMed PMID: 20739906; PubMed Central PMCID: PMC2993694. 13: Pendyala L, Yin X, Li J, Shinke T, Xu Y, Chen JP, King SB 3rd, Colley K, Goodchild T, Chronos N, Hou D. Polymer-free cerivastatin-eluting stent shows superior neointimal inhibition with preserved vasomotor function compared to polymer-based paclitaxel-eluting stent in rabbit iliac arteries. EuroIntervention. 2010 May;6(1):126-33. doi: 10.4244/. PubMed PMID: 20542808. 14: Huić M, Anić B, Cikes N, Bosnić D, Sentić M, Markeljević J, Mayer M, Pazanin L. [Myopathy with rhabdomyolysis as an adverse effect of simultaneous treatment with cerivastatin and gemfibrozil]. Lijec Vjesn. 2002 Mar-Apr;124(3-4):73-6. Croatian. PubMed PMID: 18956824. 15: Ebben MR, Sethi NK, Spielman AJ. Severe obstructive sleep apnea after cerivastatin therapy: a case report. J Clin Sleep Med. 2008 Jun 15;4(3):255-6. PubMed PMID: 18595439; PubMed Central PMCID: PMC2546459. 16: Reaume KT, Erickson SR, Dorsch MP, Dunham NL, Hiniker SM, Prabhakar N, Kline-Rogers EM, Eagle KA. Effects of cerivastatin withdrawal on statin persistence. Ann Pharmacother. 2008 Jul;42(7):956-61. doi: 10.1345/aph.1K575. Epub 2008 Jun 3. PubMed PMID: 18523235. 17: Paine SW, Parker AJ, Gardiner P, Webborn PJ, Riley RJ. Prediction of the pharmacokinetics of atorvastatin, cerivastatin, and indomethacin using kinetic models applied to isolated rat hepatocytes. Drug Metab Dispos. 2008 Jul;36(7):1365-74. doi: 10.1124/dmd.107.019455. Epub 2008 Apr 21. PubMed PMID: 18426955. 18: Chaudhry MZ, Wang JH, Blankson S, Redmond HP. Statin (cerivastatin) protects mice against sepsis-related death via reduced proinflammatory cytokines and enhanced bacterial clearance. Surg Infect (Larchmt). 2008 Apr;9(2):183-94. doi: 10.1089/sur.2006.077. PubMed PMID: 18426351. 19: Holoshitz N, Alsheikh-Ali AA, Karas RH. Relative safety of gemfibrozil and fenofibrate in the absence of concomitant cerivastatin use. Am J Cardiol. 2008 Jan 1;101(1):95-7. Epub 2007 Nov 26. PubMed PMID: 18157972. 20: Scharnagl H, Stojakovic T, Winkler K, Rosinger S, März W, Boehm BO. The HMG-CoA reductase inhibitor cerivastatin lowers advanced glycation end products in patients with type 2 diabetes. Exp Clin Endocrinol Diabetes. 2007 Jun;115(6):372-5. PubMed PMID: 17701882.