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Revision as of 13:11, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 458447950 of page Rosuvastatin for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'DrugBank', 'ChEMBL', 'ChEBI', 'KEGG', 'StdInChI'...  Latest revision as of 07:01, 29 December 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,178 edits Undid revision 1265911396 by Dexterdoct (talk) remove primary text not based on WP:MEDRSTag: Undo 
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{{Short description|Statin medication}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=May 2022}}
{{Drugbox
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 458446788
| verifiedrevid = 464383832
| IUPAC_name = (3''R'',5''S'',6''E'')-7--3,5-dihydroxyhept-6-enoic acid
| image = Rosuvastatin-Formulae V 1.png | image = Rosuvastatin structure.svg
| width = 266 | width = 275
| alt =
| image2 = Rosuvastatin_3D_Ball_and_Stick.png
| image2 = Rosuvastatin-3D-balls.png
| alt2 =
| USAN = Rosuvastatin calcium


<!--Clinical data--> <!-- Clinical data -->
| pronounce = {{IPAc-en|r|oʊ|ˈ|s|uː|v|ə|s|t|æ|t|ɪ|n}} {{respell|roh|SOO|və-stat-in}}
| tradename = Crestor
| tradename = Crestor, others
| Drugs.com = {{drugs.com|monograph|crestor}}
| Drugs.com = {{drugs.com|monograph|rosuvastatin-calcium}}
| MedlinePlus = a603033 | MedlinePlus = a603033
| DailyMedID = Rosuvastatin
| pregnancy_AU = D | pregnancy_AU = D
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Rosuvastatin Use During Pregnancy | website=Drugs.com | date=27 September 2019 | url=https://www.drugs.com/pregnancy/rosuvastatin.html | access-date=14 March 2020 | archive-date=30 November 2020 | archive-url=https://web.archive.org/web/20201130152103/https://www.drugs.com/pregnancy/rosuvastatin.html | url-status=live }}</ref>
| pregnancy_US = X
| pregnancy_category = | pregnancy_category =
| routes_of_administration = ] (by mouth)
| class =
| ATC_prefix = C10
| ATC_suffix = AA07
| ATC_supplemental = {{ATC|A10|BH52}}, {{ATC|C10|BX05}}, {{ATC|C10|BX09}}, {{ATC|C10|BA06}}, {{ATC|C10|BA09}}, {{ATC|C10|BX16}}, {{ATC|C10|BA07}}, {{ATC|C10|BX17}}, {{ATC|C10|BX10}}, {{ATC|C10|BX07}}, {{ATC|C10|BX14}}, {{ATC|C10|BX13}}, {{ATC|C10|BX22}}

<!-- Legal status -->
| legal_AU = S4 | legal_AU = S4
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Crestor Product information | website=Health Canada | date=25 April 2012 | url=https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=71404 | access-date=9 July 2021 | archive-date=9 July 2021 | archive-url=https://web.archive.org/web/20210709193244/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=71404 | url-status=live }}</ref>
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = POM | legal_UK = POM
| legal_UK_comment = <ref name="Crestor SmPC">{{cite web | title=Crestor 10mg film-coated tablets - Summary of Product Characteristics (SmPC) | website=(emc) | date=29 September 2020 | url=https://www.medicines.org.uk/emc/product/7559/smpc | access-date=9 July 2021 | archive-date=9 July 2021 | archive-url=https://web.archive.org/web/20210709193243/https://www.medicines.org.uk/emc/product/7559/smpc | url-status=live }}</ref>
| legal_US = Rx-only | legal_US = Rx-only
| legal_US_comment = <ref name="Crestor FDA label" />
| legal_status =
| legal_EU =
| routes_of_administration = oral
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = Rx-only


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = 20%<ref name=PK>{{cite journal | vauthors = Aggarwal RK, Showkathali R |title=Rosuvastatin calcium in acute coronary syndromes|journal=Expert Opinion on Pharmacotherapy|date=June 2013|volume=14|issue=9|pages=1215–27|doi=10.1517/14656566.2013.789860|pmid=23574635|s2cid=20221457 }}</ref><ref name=AHFS2018/>
| bioavailability = 20%
| protein_bound = 88%<ref name=PK/><ref name=AHFS2018/>
| metabolism = ]
| metabolism = ]: ] (major) and ]-mediated; ~10% metabolized<ref name=PK/><ref name=AHFS2018/>
| elimination_half-life = 19 h
| metabolites = ''N''-desmethyl rosuvastatin (major; 1/6–1/9 of rosuvastatin activity)<ref name="Crestor FDA label" />
| excretion = Urine / Faeces
| onset =
| elimination_half-life = 19 hours<ref name=PK/><ref name=AHFS2018/>
| duration_of_action =
| excretion = ] (90%)<ref name=PK/><ref name=AHFS2018/>


<!--Identifiers--> <!-- Identifiers -->
| index2_label = calcium salt
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 287714-41-4 | CAS_number = 287714-41-4
| CAS_number2_Ref = {{cascite|correct|CAS}}
| ATC_prefix = C10
| CAS_number2 = 147098-20-2
| ATC_suffix = AA07
| PubChem = 446157
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB01098
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106377
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 413KH5ZJ73 | UNII = 413KH5ZJ73
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 83MVU38M7Q
| PubChem = 446157
| PubChem2 = 5282455
| IUPHAR_ligand = 2954
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01098
| DrugBank2 = DBSALT000154
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 393589
| ChemSpiderID2 = 4445607
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = <!-- blanked - oldvalue: D01915 --> | KEGG = D08492
| KEGG2 = D01915
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = <!-- blanked - oldvalue: 38545 -->
| ChEBI = 38545
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEBI2 = 77249
| ChEMBL = <!-- blanked - oldvalue: 1496 -->
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| C=22 | H=28 | F=1 | N=3 | O=6 | S=1
| ChEMBL = 1496
| molecular_weight = 481.539
| ChEMBL2 = 1744447
| smiles = O=S(=O)(N(c1nc(c(c(n1)C(C)C)/C=C/(O)C(O)CC(=O)O)c2ccc(F)cc2)C)C
| NIAID_ChemDB =
| InChI = 1/C22H28FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32/h5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30)/b10-9+/t16-,17-/m1/s1
| PDB_ligand = FBI
| InChIKey = BPRHUIZQVSMCRT-VEUZHWNKBK
| synonyms =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C22H28FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32/h5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30)/b10-9+/t16?,17-/m0/s1
<!-- Chemical and physical data -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| IUPAC_name = (3''R'',5''S'',6''E'')-7--3,5-dihydroxyhept-6-enoic acid
| StdInChIKey = BPRHUIZQVSMCRT-RUEVOVDXSA-N
| C=22 | H=28 | F=1 | N=3 | O=6 | S=1
| SMILES = OC(=O)C(O)C(O)\C=C\c1c(C(C)C)nc(N(C)S(=O)(=O)C)nc1c2ccc(F)cc2
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C22H28FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32/h5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30)/b10-9+/t16-,17-/m1/s1
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = BPRHUIZQVSMCRT-VEUZHWNKSA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}} }}

<!-- Definition and medical uses -->
'''Rosuvastatin''', sold under the brand name '''Crestor''' among others, is a ] medication, used to prevent ] in those at high risk and treat ].<ref name=AHFS2018/> It is recommended to be used together with dietary changes, exercise, and weight loss.<ref name=AHFS2018/> It is taken ] (by mouth).<ref name=AHFS2018>{{cite web |title=Rosuvastatin Calcium Monograph for Professionals |url=https://www.drugs.com/monograph/rosuvastatin-calcium.html |website=Drugs.com |publisher=] (AHFS) |access-date=24 December 2018 |archive-date=24 December 2018 |archive-url=https://web.archive.org/web/20181224170456/https://www.drugs.com/monograph/rosuvastatin-calcium.html |url-status=live }}</ref>

<!-- Side effects and mechanism -->
Common side effects include abdominal pain, nausea, headaches, and ].<ref name=AHFS2018/> Serious side effects may include ], liver problems, and ].<ref name=AHFS2018/> Use during ] may harm the baby.<ref name=AHFS2018/> Like all statins, rosuvastatin works by inhibiting ], an ] found in the ] that plays a role in producing ].<ref name=AHFS2018/>

<!-- Society and culture -->
Rosuvastatin was patented in 1991 and approved for medical use in the United States in 2003.<ref name=AHFS2018/><ref name=Fis2006>{{cite book| vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9783527607495|page=473|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA473 |access-date=27 August 2020|archive-date=12 January 2023|archive-url=https://web.archive.org/web/20230112030119/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA473|url-status=live}}</ref> It is available as a ].<ref name=AHFS2018/> In 2022, it was the thirteenth most commonly prescribed medication in the United States, with more than 37{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Rosuvastatin Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Rosuvastatin | access-date = 30 August 2024 }}</ref> In Australia, it was one of the top 10 most prescribed medications between 2017 and 2023.<ref>{{cite web | title=Medicines in the health system | website=Australian Institute of Health and Welfare | date=2 July 2024 | url=https://www.aihw.gov.au/reports/medicines/medicines-in-the-health-system | access-date=30 September 2024}}</ref>

==Medical uses==
]

The primary use of rosuvastatin is for the prevention of cardiovascular disease in those at high risk and the treatment of ].<ref name=AHFS2018/>

===Effects on cholesterol levels===
The effects of rosuvastatin on ] (LDL) cholesterol are dose-related. Higher doses were more efficacious in improving the lipid profile of patients with hypercholesterolemia than milligram-equivalent doses of ] and milligram-equivalent or higher doses of ] and ].<ref name="Jones-2003">{{cite journal | vauthors=Jones PH, Davidson MH, Stein EA, Bays HE, McKenney JM, Miller E, Cain VA, Blasetto JW | title=Comparison of the efficacy and safety of rosuvastatin versus atorvastatin, simvastatin, and pravastatin across doses (STELLAR Trial) | journal=Am J Cardiol | year=2003 | volume=92 | issue=2 | pages=152–60 | pmid=12860216 | doi=10.1016/S0002-9149(03)00530-7}}</ref>

Meta-analysis showed that rosuvastatin can modestly increase levels of ] (HDL) cholesterol, as well as with other statins.<ref name="pmid=18553127">{{cite journal | vauthors = McTaggart F | title = Effects of statins on high-density lipoproteins: a potential contribution to cardiovascular benefit. | journal = Cardiovasc Drugs Ther| volume = 22 | issue = 4|date=August 2008 | pmid = 18553127 | pages = 321–38 | doi=10.1007/s10557-008-6113-z | pmc=2493531}}</ref> A 2014 Cochrane review determined there was good evidence for rosuvastatin lowering non-HDL levels linearly with dose.<ref name="pmid25415541" />

==Side effects and contraindications==
Side effects are uncommon:<ref name=MedLine>{{cite web|title=Rosuvastatin|url=https://www.nlm.nih.gov/medlineplus/druginfo/meds/a603033.html|work=MedlinePlus|publisher=U.S. National Library of Medicine|access-date=1 December 2012|date=15 June 2012|archive-date=6 November 2012|archive-url=https://web.archive.org/web/20121106160905/http://www.nlm.nih.gov/medlineplus/druginfo/meds/a603033.html|url-status=live}}</ref>
* ]
* ]
* ]
* ]
* ]
* ]
* ]
* ] or ]
* ]

The following rare side effects are more serious. Like all statins, rosuvastatin can possibly cause ], ]:<ref name=MedLine/><ref name="Crestor FDA label" />
* ], tenderness, or weakness
* lack of energy
* ]
* ]
* ]: yellowing of the skin or eyes
* dark colored, or foamy ]
* pain in the upper right part of the ]
* ]
* ]
* weakness
* unusual bleeding or bruising
* ]
* ]-like symptoms
* ], ], or other signs of ]

Allergic reactions can develop:<ref name="Crestor FDA label" />
* ]
* ]
* ]ing
* difficulty ] or ]
* swelling of the face, throat, tongue, lips, eyes, hands, feet, ankles, or lower legs
* ]
* ] or ] in fingers or toes

Rosuvastatin has multiple ]s, including hypersensitivity to rosuvastatin or any component of the formulation, active liver disease, elevation of serum ]s, pregnancy, or breastfeeding.<ref name="Crestor FDA label">{{cite web | title=Crestor- rosuvastatin calcium tablet, film coated | website=DailyMed | date=9 November 2018 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=bb0f3b5e-4bc6-41c9-66b9-6257e2513512 | access-date=14 March 2020 | archive-date=25 September 2020 | archive-url=https://web.archive.org/web/20200925143007/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=bb0f3b5e-4bc6-41c9-66b9-6257e2513512 | url-status=live }}</ref> Rosuvastatin is not prescribed nor used while pregnant, as it can cause serious harm to the fetus.<ref name="Crestor FDA label" /> In the case of breastfeeding, it is unknown whether rosuvastatin is passed through breast milk.<ref name="Crestor FDA label" /><ref name=LactMed>{{cite web|title=Rosuvastatin|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~jLYVIr:1|work=LactMed|publisher=U.S. National Library of Medicine|access-date=1 December 2012|archive-url=https://web.archive.org/web/20160107115521/http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?.%2Ftemp%2F~jLYVIr%3A1|archive-date=7 January 2016|url-status=dead}}</ref>

The risk of myopathy may be increased in Asian Americans: "Because Asians appear to process the drug differently, half the standard dose can have the same cholesterol-lowering benefit in those patients, though a full dose could increase the risk of side effects, a study by the drug's manufacturer, ], indicated."<ref>{{cite news |url=https://www.latimes.com/archives/la-xpm-2005-mar-03-na-crestor3-story.html |title=FDA Advisory Targets Asian Patients |work=] |date=3 March 2005 | vauthors = Alonso-Zaldivar R |access-date=15 March 2020 |archive-date=5 March 2016 |archive-url=https://web.archive.org/web/20160305071949/http://articles.latimes.com/2005/mar/03/nation/na-crestor3 |url-status=live }}</ref><ref>{{cite journal |vauthors=Wu HF, Hristeva N, Chang J, Liang X, Li R, Frassetto L, Benet LZ |title=Rosuvastatin Pharmacokinetics in Asian and White Subjects Wild Type for Both OATP1B1 and BCRP Under Control and Inhibited Conditions |journal=J Pharm Sci |volume=106 |issue=9 |pages=2751–2757 |date=September 2017 |pmid=28385543 |pmc=5675025 |doi=10.1016/j.xphs.2017.03.027 }}</ref><ref>{{cite journal |vauthors=Lee VW, Chau TS, Leung VP, Lee KK, Tomlinson B |title=Clinical efficacy of rosuvastatin in lipid management in Chinese patients in Hong Kong |journal=Chin. Med. J. |volume=122 |issue=23 |pages=2814–9 |date=December 2009 |pmid=20092783 |url=https://journals.lww.com/cmj/FullText/2009/12010/Clinical_efficacy_of_rosuvastatin_in_lipid.3.aspx |access-date=30 October 2019 |archive-date=30 October 2019 |archive-url=https://web.archive.org/web/20191030192433/https://journals.lww.com/cmj/FullText/2009/12010/Clinical_efficacy_of_rosuvastatin_in_lipid.3.aspx |url-status=live }}</ref> Therefore, the lowest dose is recommended in Asians.<ref>{{cite web | title=FDA Updates Crestor Warning Information | website=WebMD | date=3 March 2005 | url=https://www.webmd.com/cholesterol-management/news/20050303/fda-updates-crestor-warning-information | access-date=14 March 2020 | archive-date=20 September 2020 | archive-url=https://web.archive.org/web/20200920092759/https://www.webmd.com/cholesterol-management/news/20050303/fda-updates-crestor-warning-information | url-status=live }}</ref>

===Myopathy===
As with all statins, there is a concern of ], a severe undesired side effect. The U.S. ] (FDA) has indicated that "it does not appear that the risk is greater with Crestor than with other marketed statins", but has mandated that a warning about this side-effect, as well as a kidney toxicity warning, be added to the product label.<!--
--><ref name="FDAlabel">{{cite web|title=FDA Alert (03/2005) - Rosuvastatin Calcium (marketed as Crestor) Information |url=https://www.fda.gov/cder/drug/infopage/rosuvastatin/default.htm |date=14 March 2005 |publisher=U.S. ] (FDA) |access-date=20 March 2005 |archive-url=https://web.archive.org/web/20050305033448/https://www.fda.gov/cder/drug/infopage/rosuvastatin/default.htm |archive-date=5 March 2005 |url-status=dead }} - This page is subject to change; the date reflects the last revision date.</ref><ref name="FDA Rosuvastatin Safety">{{cite web | title=Rosuvastatin Calcium (marketed as Crestor) Information | website=U.S. ] (FDA) | date=10 July 2015 | url=http://www.fda.gov/drugs/postmarket-drug-safety-information-patients-and-providers/rosuvastatin-calcium-marketed-crestor-information | access-date=14 March 2020 | archive-date=15 December 2019 | archive-url=https://web.archive.org/web/20191215235005/https://www.fda.gov/drugs/postmarket-drug-safety-information-patients-and-providers/rosuvastatin-calcium-marketed-crestor-information | url-status=live }}</ref>

===Diabetes mellitus===
] increase the risk of ],<ref>{{cite journal | vauthors = Sattar N, Preiss D, Murray HM, Welsh P, Buckley BM, de Craen AJ, Seshasai SR, McMurray JJ, Freeman DJ, Jukema JW, Macfarlane PW, Packard CJ, Stott DJ, Westendorp RG, Shepherd J, Davis BR, Pressel SL, Marchioli R, Marfisi RM, Maggioni AP, Tavazzi L, Tognoni G, Kjekshus J, Pedersen TR, Cook TJ, Gotto AM, Clearfield MB, Downs JR, Nakamura H, Ohashi Y, Mizuno K, Ray KK, Ford I |title=Statins and risk of incident diabetes: a collaborative meta-analysis of randomised statin trials.|journal=Lancet|date=February 2010|volume=375|issue=9716|pages=735–42|pmid=20167359|doi=10.1016/S0140-6736(09)61965-6|s2cid=11544414 }}</ref> consistent with FDA's review, which reported a 27% increase in investigator-reported diabetes mellitus in rosuvastatin-treated people.<ref>{{cite web |url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-important-safety-label-changes-cholesterol-lowering-statin-drugs |title=FDA Drug Safety Communication: Important safety label changes to cholesterol-lowering statin drugs |publisher=U.S. ] (FDA) |date=9 February 2019 |access-date=15 March 2020 |archive-date=15 March 2020 |archive-url=https://web.archive.org/web/20200315023515/https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-important-safety-label-changes-cholesterol-lowering-statin-drugs |url-status=live }}</ref>

==Drug interactions==
The following drugs can have negative interactions with rosuvastatin and should be discussed with the prescribing doctor:<ref name=MedLine/><ref name="Crestor FDA label" />
* Coumadin ]s ('blood thinners', e.g. ]) can affect the removal of rosuvastatin
* ], ]
* Drugs that may decrease the levels or activity of endogenous steroid hormones, e.g. ], ], and ]
* Additional medications for high cholesterol such as ], ], ], and ] (when taken in lipid-modifying doses of 1 g/day and above)
* Specific ]s including ] (when taken with ]), ] and ]
* Alcohol intake should be reduced while on rosuvastatin to decrease the risk of developing liver damage<ref name="Crestor FDA label" />
* Aluminum and magnesium hydroxide antacids should not be taken within two hours of taking rosuvastatin<ref name="Crestor FDA label" />
* Coadministration of rosuvastatin with ] may increase the risk of rhabdomyolysis and ]<ref name = "Viberzi FDA label">{{cite web | title=Viberzi- eluxadoline tablet, film coated | website=DailyMed | date=19 June 2018 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7821bd40-4c84-4984-951b-6436ae20421a | access-date=14 March 2020 | archive-date=28 September 2020 | archive-url=https://web.archive.org/web/20200928020742/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7821bd40-4c84-4984-951b-6436ae20421a | url-status=live }}</ref>

Grapefruit juice negatively interacts with several specific drugs in the statin class, but it has little or no effect on rosuvastatin.<ref name="Bailey_2013">{{cite journal | vauthors = Bailey DG, Dresser G, Arnold JM | title = Grapefruit-medication interactions: forbidden fruit or avoidable consequences? | journal = CMAJ | volume = 185 | issue = 4 | pages = 309–316 | date = March 2013 | pmid = 23184849 | pmc = 3589309 | doi = 10.1503/cmaj.120951 | doi-access = free }}</ref>

==Structure==
Rosuvastatin has structural similarities with most other ]s, e.g., ], ] and ], but unlike other statins, rosuvastatin contains ] (in ] functional group).
Crestor is a ] salt of rosuvastatin, i.e. rosuvastatin calcium,<ref name="FDAlabel"/> in which calcium replaces the hydrogen in the ] group on the right of the skeletal formula at the top right of this page.{{citation needed|date=May 2022}}

==Mechanism of action==
{{Further|Statin}}

Rosuvastatin is a ] of the enzyme ], having a mechanism of action similar to that of other statins.<!--
--><ref name="ASTEROID">{{cite journal | vauthors = Nissen SE, Nicholls SJ, Sipahi I, Libby P, Raichlen JS, Ballantyne CM, Davignon J, Erbel R, Fruchart JC, Tardif JC, Schoenhagen P, Crowe T, Cain V, Wolski K, Goormastic M, Tuzcu EM |title=Effect of very high-intensity statin therapy on regression of coronary atherosclerosis: the ASTEROID trial |journal=JAMA |volume=295 |issue=13 |pages=1556–65 |date = April 2006 |pmid=16533939 |doi=10.1001/jama.295.13.jpc60002 |doi-access= | title-link=doi }}</ref>

Putative beneficial effects of rosuvastatin therapy on chronic ] may be negated by increases in collagen turnover markers as well as a reduction in plasma ] levels in patients with chronic heart failure.<ref>{{cite journal | vauthors = Ashton E, Windebank E, Skiba M, Reid C, Schneider H, Rosenfeldt F, Tonkin A, Krum H |title=Why did high-dose rosuvastatin not improve cardiac remodeling in chronic heart failure? Mechanistic insights from the UNIVERSE study |journal=Int J Cardiol |volume= 146|issue= 3|pages= 404–7|date=February 2011 |pmid=20085851 |doi=10.1016/j.ijcard.2009.12.028 }}</ref>

==Pharmacodynamics==

The dose-related magnitude of rosuvastatin on blood lipids was determined in a ] systematic review in 2014. Over the dose range of 1 to 80&nbsp;mg/day strong linear dose‐related effects were found; total cholesterol was reduced by 22.1% to 44.8%, LDL cholesterol by 31.2% to 61.2%, non-HDL cholesterol by 28.9% to 56.7% and triglycerides by 14.4% to 26.6%.<ref name="pmid25415541">{{cite journal|title=Rosuvastatin for lowering lipids |journal=The Cochrane Database of Systematic Reviews|issue=11 | vauthors = Adams SP, Sekhon SS, Wright JM |date=November 2014 |volume=2014 |pages=CD010254|doi=10.1002/14651858.cd010254.pub2|pmid=25415541|pmc=6463960 | doi-access = free | title-link = doi }}</ref>

==Pharmacokinetics==
Absolute ] of rosuvastatin is about 20% and ] is reached in 3 to 5 hours; administration with food did not affect the ] according to the original sponsor submitted clinical study and as per product label.<ref name="Crestor FDA label" /> However, a subsequent clinical study has shown a marked reduction in rosuvastatin exposure when administered with food.<ref>{{cite journal | vauthors = Li Y, Jiang X, Lan K, Zhang R, Li X, Jiang Q |date=October 2007|title=Pharmacokinetic properties of rosuvastatin after single-dose, oral administration in Chinese volunteers: a randomized, open-label, three-way crossover study|journal=Clinical Therapeutics|volume=29|issue=10|pages=2194–203|doi=10.1016/j.clinthera.2007.10.005|pmid=18042475 }}</ref> It is 88% ], mainly to ].<ref name=AHFS2018/> Fraction absorbed of rosuvastatin is frequently misquoted in the literature as approximately 0.5 (50%)<ref>{{cite journal | vauthors = Bergman E, Lundahl A, Fridblom P, Hedeland M, Bondesson U, Knutson L, Lennernäs H |date=December 2009|title=Enterohepatic disposition of rosuvastatin in pigs and the impact of concomitant dosing with cyclosporine and gemfibrozil |journal=Drug Metabolism and Disposition|volume=37|issue=12|pages=2349–58|doi=10.1124/dmd.109.029363|pmid=19773540|s2cid=24783238 }}</ref> due to a miscalculated hepatic extraction ratio in the original submission package subsequently corrected by the FDA reviewer.<ref>{{Cite web|url=http://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-366_Crestor.cfm|title=Page 45 of FDA Drug Approval Package, Clinical Pharmacology Biopharmaceutics Review(s) (PDF)|date=29 January 2004|publisher=U.S. ] (FDA)|access-date=22 June 2016|archive-date=28 August 2016|archive-url=https://web.archive.org/web/20160828094451/http://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-366_Crestor.cfm|url-status=live}}</ref>

Rosuvastatin is metabolized mainly by ] and not extensively metabolized; approximately 10% is recovered as ] ''N''-desmethyl rosuvastatin. It is excreted in ] (90%) primarily and the ] is approximately 19 hours.<ref name="Crestor FDA label" /><ref name=AHFS2018/>

Both AUC and C<sub>max</sub> are approximately 2-fold higher in Asian patients compared to Caucasian patients given the same dose of rosuvastatin.<ref name="Crestor FDA label" />

==Society and culture==
Rosuvastatin is the ].<ref name="INN">{{cite web | title = International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 45 | url = https://www.who.int/medicines/publications/druginformation/innlists/RL45.pdf | publisher = World Health Organization | access-date = 29 November 2016 | page = 50 | date = 2001 | archive-date = 18 May 2016 | archive-url = https://web.archive.org/web/20160518192927/http://www.who.int/medicines/publications/druginformation/innlists/RL45.pdf | url-status = live }}</ref>

===Economics===
Because low- to moderate dose statins are strongly recommended by the ] (USPSTF) for ] of cardiovascular disease in adults aged 40–75 years who are at risk,<ref name=USPSTFstatins>{{cite journal | title=Statin Use for the Primary Prevention of Cardiovascular Disease in Adults: Recommendation Statement | journal=American Family Physician | volume=95 | issue=2 | date=January 2017 | url=https://www.aafp.org/afp/2017/0115/od1.html | access-date=9 May 2022 | archive-date=3 August 2020 | archive-url=https://web.archive.org/web/20200803014843/https://www.aafp.org/afp/2017/0115/od1.html | url-status=live }}</ref> the ] (PPACA) in the United States requires most health insurance plans to cover the costs of these drugs without charging the insured patient a ] or ], even if he or she has not yet reached his or her annual ].<ref name="AZHR">{{cite web |title=Affordable Care Act (ACA)-Essential Health Benefit (EHB) Zero Dollar Copay Preventive Medication List White Paper |url=https://benefitoptions.az.gov/sites/default/files/PHARM_F_Essential_Health_Benefit_List.pdf |website=Arizona Department of Administration Human Resources |publisher=State of Arizona |access-date=8 May 2022 |archive-date=3 March 2022 |archive-url=https://web.archive.org/web/20220303022220/https://benefitoptions.az.gov/sites/default/files/PHARM_F_Essential_Health_Benefit_List.pdf |url-status=live }}</ref><ref name="HealthcareDotGovPreventiveCare">{{cite web |title=Preventive care benefits for adults |url=https://www.healthcare.gov/preventive-care-adults/ |website=] |publisher=] |access-date=7 May 2022 |archive-date=7 May 2022 |archive-url=https://web.archive.org/web/20220507192559/https://www.healthcare.gov/preventive-care-adults/ |url-status=live }}</ref><ref name="KFFACApreventive">{{cite web |title=Preventive Services Covered by Private Health Plans under the Affordable Care Act |date=4 August 2015 |url=https://www.kff.org/health-reform/fact-sheet/preventive-services-covered-by-private-health-plans/ |publisher=] |access-date=7 May 2022 |archive-date=2 May 2022 |archive-url=https://web.archive.org/web/20220502082404/https://www.kff.org/health-reform/fact-sheet/preventive-services-covered-by-private-health-plans/ |url-status=live }}</ref> Rosuvastatin 5&nbsp;mg and 10&nbsp;mg are examples of regimens meeting the USPSTF guideline;<ref name=USPSTFstatins/> however, insurers have discretion as to which low- and moderate-dose statin regimens to cover under this requirement,<ref name=ACApreventiveFAQ>{{cite web | title=Affordable Care Act Implementation FAQs - Set 12 | website=CMS | date=22 April 2013 | url=https://www.cms.gov/CCIIO/Resources/Fact-Sheets-and-FAQs/aca_implementation_faqs12 | access-date=7 May 2022 | archive-date=5 May 2022 | archive-url=https://web.archive.org/web/20220505071209/https://www.cms.gov/CCIIO/Resources/Fact-Sheets-and-FAQs/aca_implementation_faqs12 | url-status=live }}</ref> and some only cover other statins.<ref>{{cite web|url=https://www.uhc.com/content/dam/uhcdotcom/en/Pharmacy/PDFs/UHC-SignatureValue-Formulary-PPACA-ZeroCost-Preventive-Meds-Eff-Sept-2021.pdf|date=September 2021|title=SignatureValue Zero Cost Share Preventive Medications PDL|website=Uhc.com|access-date=26 May 2022|archive-date=5 February 2022|archive-url=https://web.archive.org/web/20220205144210/https://www.uhc.com/content/dam/uhcdotcom/en/Pharmacy/PDFs/UHC-SignatureValue-Formulary-PPACA-ZeroCost-Preventive-Meds-Eff-Sept-2021.pdf|url-status=live}}</ref>

The drug was billed as a "super-statin" during its clinical development; the claim was that it offered high potency and improved cholesterol reduction compared to rivals in the class. The main competitors to rosuvastatin are ] and ]. However, people can also combine ] with either simvastatin or atorvastatin and other agents on their own, for somewhat similar augmented response rates. {{as of|2006}} some published information for comparing rosuvastatin, atorvastatin, and ezetimibe/simvastatin results are available, but many of the relevant studies are still{{when|date=October 2019}} in progress.<ref name="ASTEROID"/>{{update inline|date=July 2021}}

First launched in 2003, sales of rosuvastatin were $129{{nbsp}}million and $908{{nbsp}}million in 2003, and 2004, respectively, with a total patient treatment population of over 4{{nbsp}}million by the end of 2004.{{Citation needed|date=January 2008}}
Annual cost to the UK ] (NHS) in 2018, for 5–40&nbsp;mg rosuvastatin daily (of one person) was £24-40, compared to £10-20 for 20–80&nbsp;mg simvastatin.<ref>{{Cite web|url=http://gmmmg.nhs.uk/docs/cost_comparison_charts.pdf|title=COST COMPARISON CHARTS|publisher=REGIONAL DRUG AND THERAPEUTICS CENTRE (NEWCASTLE)|date=August 2018|access-date=4 December 2018|archive-date=20 October 2018|archive-url=https://web.archive.org/web/20181020032741/http://gmmmg.nhs.uk/docs/cost_comparison_charts.pdf|url-status=dead}}</ref>

In 2013, it was the fourth-highest-selling drug in the United States, accounting for approximately $5.2{{nbsp}}billion in sales.<ref>{{cite web|title=Top 100 Drugs for Q2 2013 by Sales|url=https://www.drugs.com/stats/top100/sales|access-date=24 August 2013|archive-date=23 June 2018|archive-url=https://web.archive.org/web/20180623222024/https://www.drugs.com/stats/top100/sales|url-status=live}}</ref> In 2021, it was the thirteenth most commonly prescribed medication in the United States, with more than 32{{nbsp}}million prescriptions.<ref name="Rosuvastatin - Drug Usage Statistics">{{cite web | title=Rosuvastatin - Drug Usage Statistics | website=ClinCalc | url=https://clincalc.com/DrugStats/Drugs/Rosuvastatin | access-date=14 January 2024}}</ref>

===Legal status===
Rosuvastatin is approved in the United States for the treatment of high ] (]), total cholesterol (]), and/or ]s (]).<ref name="pill">{{cite web | title=Core Data Sheet, Crestor Tablets | url=http://www.crestor.info/gUserFiles/CRESTOR_CDS_10_40_mg_FINAL_170603.pdf | date=17 June 2003 | publisher=] | access-date=20 March 2005 | archive-url=https://web.archive.org/web/20050508053622/http://www.crestor.info/gUserFiles/CRESTOR_CDS_10_40_mg_FINAL_170603.pdf | archive-date=8 May 2005 | url-status=dead | df=mdy-all }} - NOTE: this is provider-oriented information and should not be used without the supervision of a physician.</ref> In February 2010, rosuvastatin was approved by the FDA for the primary prevention of cardiovascular events.<ref name="fdaap">{{Cite report|url=http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2010/021366s016ltr.pdf|publisher=U.S. ] (FDA)|id=NDA 21366/S-016|title=Supplement approval - CRESTOR (rosuvastatin calcium) Tablets | vauthors = Colman EC |date=8 February 2010|access-date=31 October 2010|archive-date=17 October 2012|archive-url=https://web.archive.org/web/20121017170917/http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2010/021366s016ltr.pdf|url-status=live}}</ref>

{{As of|2004}}, rosuvastatin had been approved in 154 countries and launched in 56. Approval in the United States by the ] (FDA) came on 13 August 2003.<ref>{{cite web | title=Drug Approval Package: Crestor (Rosuvastatin Calcium) NDA #021366 | website=U.S. ] (FDA) | date=29 January 2004 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-366_Crestor.cfm | access-date=15 March 2020 | archive-date=6 August 2020 | archive-url=https://web.archive.org/web/20200806005318/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-366_Crestor.cfm | url-status=live }}</ref><ref name="FDAapproval">{{cite news|title=FDA Approves New Drug for Lowering Cholesterol |url=https://www.fda.gov/bbs/topics/ANSWERS/2003/ANS01247.html |date=12 August 2003 |publisher=U.S. ] (FDA) |access-date=20 March 2005 |archive-url=https://web.archive.org/web/20050207153150/https://www.fda.gov/bbs/topics/ANSWERS/2003/ANS01247.html |archive-date=7 February 2005 |url-status=dead }}</ref>

===Patent protection and generic versions===
The main patent that protected rosuvastatin (RE37,314, which expired in 2016) was challenged as being an improper reissue of an earlier patent. This challenge was rejected in 2010, and thus patent protection continued until 2016.<ref>{{Cite web|url=http://www.delawareonline.com/article/20100701/BUSINESS/7010316/1003/RSS01|title=AstraZeneca's Crestor patent upheld;No generic competition until 2016|website=Delawareonline.com|access-date=26 May 2022}}{{Dead link|date=January 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref><ref>{{cite press release| url=https://www.prnewswire.com/news-releases/crestor-patent-upheld-by-us-court-97435724.html| title=Crestor Patent Upheld By US Court| access-date=25 April 2012| publisher=]| date=29 June 2010| via=PR Newswire| archive-date=27 November 2020| archive-url=https://web.archive.org/web/20201127003059/https://www.prnewswire.com/news-releases/crestor-patent-upheld-by-us-court-97435724.html| url-status=live}}</ref><ref>{{cite news| url=https://www.reuters.com/article/astrazeneca-crestor-idUSN2917115320100629| access-date=25 April 2012| date=29 June 2010| title=U.S. judge rules AstraZeneca Crestor patent valid| publisher=]| vauthors = Berkrot B, Hals T | archive-date=12 March 2016| archive-url=https://web.archive.org/web/20160312124530/http://www.reuters.com/article/astrazeneca-crestor-idUSN2917115320100629| url-status=live}}</ref><ref>{{cite news| url=https://pqasb.pqarchiver.com/delawareonline/access/2074695931.html?FMT=ABS&date=Jul+01%2C+2010| archive-url=https://archive.today/20130131145710/http://pqasb.pqarchiver.com/delawareonline/access/2074695931.html?FMT=ABS&date=Jul+01,+2010| url-status=dead| archive-date=31 January 2013| access-date=25 April 2012| title=AstraZeneca patent upheld| date=1 July 2010| newspaper=]| location=Wilmington, Delaware| vauthors = Starkey J | url-access=subscription }} {{subscription required}}</ref><ref>{{cite press release | title=Crestor US patent upheld by Court of Appeals for the Federal Circuit | website=AstraZeneca | date=14 December 2012 | url=https://www.astrazeneca.com/media-centre/press-releases/2012/CRESTOR-US-patent-upheld-by-Court-of-Appeals-for-the-Federal-Circuit-14122012.html | access-date=9 July 2021 | archive-date=9 July 2021 | archive-url=https://web.archive.org/web/20210709193242/https://www.astrazeneca.com/media-centre/press-releases/2012/CRESTOR-US-patent-upheld-by-Court-of-Appeals-for-the-Federal-Circuit-14122012.html | url-status=live }}</ref>

In April 2016, the FDA approved the first ] version of rosuvastatin (from Watson Pharmaceuticals Inc).<ref>{{cite web|title=FDA approves first generic Crestor|url=https://www.fda.gov/news-events/press-announcements/fda-approves-first-generic-crestor|publisher=U.S. ] (FDA)|access-date=3 May 2016|date=29 April 2016|archive-date=15 March 2020|archive-url=https://web.archive.org/web/20200315024145/https://www.fda.gov/news-events/press-announcements/fda-approves-first-generic-crestor|url-status=live}}</ref> In July 2016, ] gained approval for its generic rosuvastatin calcium.<ref>{{cite press release |url=https://www.prnewswire.com/news-releases/mylan-launches-generic-crestor-tablets-300301446.html |title=Mylan Launches Generic Crestor Tablets |date=20 July 2016 |publisher=] |via=PR Newswire |access-date=15 March 2020 |archive-date=9 March 2021 |archive-url=https://web.archive.org/web/20210309012223/https://www.prnewswire.com/news-releases/mylan-launches-generic-crestor-tablets-300301446.html |url-status=live }}</ref>

===Debate and criticisms===
In October 2003, several months after its introduction in Europe, ], the editor of the ] '']'', criticized the way Crestor had been introduced. "AstraZeneca's tactics in marketing its cholesterol-lowering drug, rosuvastatin, raise disturbing questions about how drugs enter clinical practice and what measures exist to protect patients from inadequately investigated medicines," according to his editorial. ''The Lancet's'' editorial position is that the data for Crestor's superiority rely too much on extrapolation from the lipid profile data (surrogate end-points) and too little on hard clinical end-points, which are available for other statins that had been on the market longer. The manufacturer responded by stating that few drugs had been tested so successfully on so many patients. In correspondence published in ''The Lancet'', AstraZeneca's CEO ] called the editorial "flawed and incorrect" and slammed the journal for making "such an outrageous critique of a serious, well-studied medicine."<!--
--><ref name="lancetoped">{{cite journal | vauthors = Horton R | title = The statin wars: why AstraZeneca must retreat | journal = Lancet | volume = 362 | issue = 9393 | pages = 1341 | date = October 2003 | pmid = 14585629 | doi = 10.1016/S0140-6736(03)14669-7 | s2cid = 39528790 | title-link = doi | doi-access = free }}<br /><!--
-->{{cite journal | vauthors = McKillop T | title = The statin wars | journal = Lancet | volume = 362 | issue = 9394 | page = 1498 | date=November 2003 | pmid = 14602449 | doi = 10.1016/S0140-6736(03)14698-3| s2cid = 5300990 | doi-access = free }}</ref>

In 2004, the consumer interest organization ] filed a ] with the FDA, asking that Crestor be withdrawn from the US market. On 11 March 2005, the FDA issued a letter to ] of Public Citizen both denying the petition and providing an extensive detailed analysis of findings that demonstrated no basis for concerns about rosuvastatin compared with the other statins approved for marketing in the United States.<ref name="FDA ruling">{{cite web | publisher=U.S. ] (FDA) | title=Docket No. 2004P-0113/CP1 | url=https://www.regulations.gov/contentStreamer?documentId=FDA-2004-P-0009-0004&attachmentNumber=1&contentType=pdf | access-date=2 July 2020 | archive-date=2 July 2020 | archive-url=https://web.archive.org/web/20200702175551/https://www.regulations.gov/contentStreamer?documentId=FDA-2004-P-0009-0004&attachmentNumber=1&contentType=pdf | url-status=live }}</ref> In 2015, Wolfe explained why he thought that "the drug should have been withdrawn and why it should not be used", due to the incidence of rhabdomyolysis, renal problems, and significant increase in ] (HbA<sub>1C</sub>) and fasting ] levels, and decreased ] in diabetic patients. Rosuvastatin indeed lowered cholesterol more than other statins, but Wolfe asked "what about actually improving health, preventing heart attacks and strokes?"<ref name=wolfe>{{cite journal | vauthors = Wolfe S | title=Rosuvastatin: winner in the statin wars, patients' health notwithstanding | journal=BMJ| volume=350 | date=March 2015 | doi=10.1136/bmj.h1388|doi-access=free | pages=h1388 | title-link=doi | pmid = 25787130 }}</ref>

==References==
{{reflist}}

{{Statins}}
{{AstraZeneca}}
{{Portal bar | Medicine}}
{{Authority control}}

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