Simvastatin

Simvastatin
Clinical data
Pronunciation	/ˈsɪmvəstætɪn/ ⓘ
Trade names	Zocor, other
AHFS/Drugs.com	Monograph
MedlinePlus	a692030
License data	US DailyMed: Simvastatin;
Pregnancy; category	AU: D;
Routes of; administration	By mouth
ATC code	C10AA01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	5%
Protein binding	95%
Metabolism	Liver (CYP3A4)
Elimination half-life	2 hours for simvastatin and 1.9 hours for simvastatin acid
Excretion	Kidney 13%, faecal 60%
Identifiers
	IUPAC name (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate;
CAS Number	79902-63-9 ;
PubChem CID	54454;
IUPHAR/BPS	2955;
DrugBank	DB00641 ;
ChemSpider	49179 ;
UNII	AGG2FN16EV;
KEGG	D00434 ;
ChEBI	CHEBI:9150 ;
ChEMBL	ChEMBL1064 ;
CompTox Dashboard (EPA)	DTXSID0023581 ;
ECHA InfoCard	100.115.749
Chemical and physical data
Formula	C25H38O5
Molar mass	418.574 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI InChI=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 ; Key:RYMZZMVNJRMUDD-HGQWONQESA-N ;
	(verify)

Simvastatin, sold under the brand name Zocor among others, is a statin, a type of lipid-lowering medication.^[3] It is used along with exercise, diet, and weight loss to decrease elevated lipid levels.^[3] It is also used to decrease the risk of heart problems in those at high risk.^[3] It is taken by mouth.^[3]

Common side effects include constipation, headaches, and nausea.^[3] Serious side effects may include muscle breakdown, liver problems, and increased blood sugar levels.^[3] A lower dose may be needed in people with kidney problems.^[3] There is evidence of harm to the developing baby when taken during pregnancy^[3]^[4] and it should not be used by those who are breastfeeding.^[3] It is in the statin class of medications and works by decreasing the manufacture of cholesterol by the liver.^[3]

Simvastatin is made from the fungus Aspergillus terreus.^[5] It was patented by Merck in 1980, and came into medical use in 1992.^[5]^[6] Simvastatin is available as a generic medication,^[3] and is on the World Health Organization's List of Essential Medicines.^[7] In 2023, it was the 22nd most commonly prescribed medication in the United States, with more than 24 million prescriptions.^[8]^[9]

^ Cite error: The named reference Zocor FDA label was invoked but never defined (see the help page).
^ "Active substance: simvastatin" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 26 November 2020.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "Simvastatin". The American Society of Health-System Pharmacists. Archived from the original on 10 January 2015. Retrieved 8 January 2015.
^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
^ ^a ^b Cechinel-Filho V (2012). Plant bioactives and drug discovery : principles, practice, and perspectives. Hoboken, N.J.: John Wiley & Sons. p. 104. ISBN 9780470582268. Archived from the original on 5 March 2016.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 472. ISBN 9783527607495.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ "Top 300 of 2023". ClinCalc. Archived from the original on 12 August 2025. Retrieved 12 August 2025.
^ "Simvastatin Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 12 August 2025.

[Zocor_FDA_label-1] Cite error: The named reference Zocor FDA label was invoked but never defined (see the help page).

[2] "Active substance: simvastatin" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 26 November 2020.

[AHFS2015-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "Simvastatin". The American Society of Health-System Pharmacists. Archived from the original on 10 January 2015. Retrieved 8 January 2015.

[4] "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.

[Cec2012-5] Cechinel-Filho V (2012). Plant bioactives and drug discovery : principles, practice, and perspectives. Hoboken, N.J.: John Wiley & Sons. p. 104. ISBN 9780470582268. Archived from the original on 5 March 2016.

[Fis2006-6] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 472. ISBN 9783527607495.

[WHO21st-7] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[Top300Drugs-8] "Top 300 of 2023". ClinCalc. Archived from the original on 12 August 2025. Retrieved 12 August 2025.

[9] "Simvastatin Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 12 August 2025.

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