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: WARNINGRx-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. It is used along with exercise, diet, and weight loss to decrease elevated lipid levels. It is also used to decrease the risk of heart problems in those at high risk. It is taken by mouth.

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

Simvastatin is made from the fungus Aspergillus terreus. It was patented by Merck in 1980, and came into medical use in 1992. Simvastatin is available as a generic medication, and is on the World Health Organization's List of Essential Medicines. In 2021, it was the sixteenth most commonly prescribed medication in the United States, with more than 30 million prescriptions.

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