Simvastatin

Simvastatin
Clinical data
Pronunciation/ˈsɪmvəstætɪn/
Trade namesZocor, other
AHFS/Drugs.comMonograph
MedlinePlusa692030
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability5%
Protein binding95%
MetabolismLiver (CYP3A4)
Elimination half-life2 hours for simvastatin and 1.9 hours for simvastatin acid
ExcretionKidney 13%, faecal 60%
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.115.749 Edit this at Wikidata
Chemical and physical data
FormulaC25H38O5
Molar mass418.574 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:RYMZZMVNJRMUDD-HGQWONQESA-N checkY
  (verify)

Simvastatin, sold under the brand name Zocor among others, is a statin, a type of lipid-lowering medication.[4] It is used along with exercise, diet, and weight loss to decrease elevated lipid levels.[4] It is also used to decrease the risk of heart problems in those at high risk.[4] It is taken by mouth.[4]

Common side effects include constipation, headaches, and nausea.[4] Serious side effects may include muscle breakdown, liver problems, and increased blood sugar levels.[4] A lower dose may be needed in people with kidney problems.[4] There is evidence of harm to the developing baby when taken during pregnancy[4][5] and it should not be used by those who are breastfeeding.[4] It is in the statin class of medications and works by decreasing the manufacture of cholesterol by the liver.[4]

Simvastatin is made from the fungus Aspergillus terreus.[6] It was patented by Merck in 1980, and came into medical use in 1992.[6][7] Simvastatin is available as a generic medication,[4] and is on the World Health Organization's List of Essential Medicines.[8] In 2022, it was the nineteenth most commonly prescribed medication in the United States, with more than 26 million prescriptions.[9][10]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  2. ^ Cite error: The named reference Zocor FDA label was invoked but never defined (see the help page).
  3. ^ "Active substance: simvastatin" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 26 November 2020.
  4. ^ 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.
  5. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  6. ^ 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.
  7. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 472. ISBN 9783527607495.
  8. ^ 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.
  9. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  10. ^ "Simvastatin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.