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Simvastatin
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{{Short description|Lipid-lowering medication}} {{Use dmy dates|date=January 2024}} {{cs1 config |name-list-style=vanc |display-authors=6}} {{Drugbox | verifiedrevid = 464391842 | image = Simvastatin.svg | image_class = skin-invert-image | width = 200 | alt = | image2 = Simvastatin3Dan.gif | image_class2 = bg-transparent | width2 = 200 | alt2 = <!--Clinical data--> | pronounce = {{IPAc-en|Λ|s|Ιͺ|m|v|Ι|s|t|Γ¦|t|α΅»|n|audio=LL-Q1860 (eng)-Naomi Persephone Amethyst (NaomiAmethyst)-simvastatin.wav}} | tradename = Zocor, other | Drugs.com = {{drugs.com|monograph|simvastatin}} | MedlinePlus = a692030 | DailyMedID = Simvastatin | pregnancy_AU = D | routes_of_administration = [[Oral administration|By mouth]] | ATC_prefix = C10 | ATC_suffix = AA01 | legal_AU = S4 | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = <ref name="Zocor FDA label" /> | legal_EU = Rx-only | legal_EU_comment = <ref>{{cite web | title = Active substance: simvastatin | work = List of nationally authorised medicinal products | url = https://www.ema.europa.eu/documents/psusa/simvastatin-list-nationally-authorised-medicinal-products-psusa/00002709/202004_en.pdf | date = 26 November 2020 | publisher = European Medicines Agency }}</ref> <!--Pharmacokinetic data--> | bioavailability = 5% | protein_bound = 95% | metabolism = [[Liver]] ([[CYP3A4]]) | elimination_half-life = 2 hours for simvastatin and 1.9 hours for simvastatin acid | excretion = [[Kidney]] 13%, [[feces|faecal]] 60% <!--Identifiers--> | IUPHAR_ligand = 2955 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 79902-63-9 | PubChem = 54454 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00641 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 49179 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = AGG2FN16EV | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D00434 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 9150 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1064 <!--Chemical data--> | IUPAC_name = (1''S'',3''R'',7''S'',8''S'',8a''R'')-8-{2-[(2''R'',4''R'')-4-hydroxy-6-oxotetrahydro-2''H''-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate | C=25 | H=38 | O=5 | smiles = O=C(O[C@@H]1[C@H]3C(=C/[C@H](C)C1)\C=C/[C@@H]([C@@H]3CC[C@H]2OC(=O)C[C@H](O)C2)C)C(C)(C)CC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RYMZZMVNJRMUDD-HGQWONQESA-N }} <!-- Definition and medical uses --> '''Simvastatin''', sold under the brand name '''Zocor''' among others, is a [[statin]], a type of [[lipid-lowering medication]].<ref name=AHFS2015>{{cite web|title=Simvastatin|url=https://www.drugs.com/monograph/simvastatin.html|publisher=The American Society of Health-System Pharmacists|access-date=8 January 2015|url-status=live|archive-url=https://web.archive.org/web/20150110101755/http://www.drugs.com/monograph/simvastatin.html|archive-date=10 January 2015}}</ref> It is used along with exercise, diet, and weight loss to decrease [[hyperlipidemia|elevated lipid levels]].<ref name=AHFS2015/> It is also used to decrease the risk of [[Cardiovascular disease|heart problems]] in those at high risk.<ref name=AHFS2015/> It is taken by mouth.<ref name=AHFS2015/> <!-- Side effects and mechanism --> Common side effects include constipation, headaches, and nausea.<ref name=AHFS2015/> Serious side effects may include [[rhabdomyolysis|muscle breakdown]], liver problems, and increased blood sugar levels.<ref name=AHFS2015/> A lower dose may be needed in people with [[chronic kidney disease|kidney problems]].<ref name=AHFS2015/> There is evidence of harm to the developing baby when taken during [[pregnancy]]<ref name=AHFS2015/><ref>{{cite web|title=Prescribing medicines in pregnancy database|url=http://www.tga.gov.au/hp/medicines-pregnancy.htm#.U1Yw8Bc3tqw|work=Australian Government|access-date=22 April 2014|date=3 March 2014|url-status=live|archive-url=https://web.archive.org/web/20140408040902/http://www.tga.gov.au/hp/medicines-pregnancy.htm#.U1Yw8Bc3tqw|archive-date=8 April 2014}}</ref> and it should not be used by those who are [[breastfeeding]].<ref name=AHFS2015/> It is in the [[statin]] class of medications and works by decreasing the manufacture of cholesterol by the liver.<ref name=AHFS2015/> <!--History, society and culture --> Simvastatin is made from the fungus ''[[Aspergillus terreus]]''.<ref name=Cec2012/> It was patented by [[Merck and Co.|Merck]] in 1980, and came into medical use in 1992.<ref name=Cec2012>{{cite book| vauthors = Cechinel-Filho V |title=Plant bioactives and drug discovery : principles, practice, and perspectives|date=2012|publisher=John Wiley & Sons|location=Hoboken, N.J.|isbn=9780470582268|page=104|url=https://books.google.com/books?id=hhraBwhymOUC&pg=PA104|url-status=live|archive-url=https://web.archive.org/web/20160305085553/https://books.google.ca/books?id=hhraBwhymOUC&pg=PA104|archive-date=5 March 2016}}</ref><ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=472 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA472 |language=en}}</ref> Simvastatin is available as a [[generic medication]],<ref name=AHFS2015/> and is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> In 2022, it was the nineteenth most commonly prescribed medication in the United States, with more than 26{{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 = Simvastatin Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Simvastatin | access-date = 30 August 2024 }}</ref>
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