simvastatin

Also known as MK-733, Zocor®, Zocor, 2,2-dimethylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one, Cholestat, Sinvacor, Simcor

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.

Chemical data

Formula: C25H38O5
Molecular weight: 418.6 g/mol
IUPAC name: [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
SMILES: CCC(C)(C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O)C
InChIKey: RYMZZMVNJRMUDD-HGQWONQESA-N
XLogP: 4.7
Polar surface area: 72.8 Å²
H-bond donors: 1
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

13,209 papers

~14 min read

Article

12 sections

Contents

Medical uses
Contraindications
Adverse effects
Interactions
Pharmacology
Pharmacodynamics
Pharmacokinetics
History
Society and culture
Economics
Brand names
References

{{Drugbox | verifiedrevid = 464391842 | image = Simvastatin.svg | image_class = skin-invert-image | width = 200 | alt = | image2 = Simvastatin3Dan.gif | image_class2 = bg-transparent | width2 = 200 | alt2 = | pronounce = | tradename = Zocor, other | Drugs.com = | MedlinePlus = a692030 | DailyMedID = Simvastatin | pregnancy_AU = D | routes_of_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 = | legal_EU = Rx-only | legal_EU_comment = | 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%, faecal 60% | IUPHAR_ligand = 2955 | CAS_number_Ref = | CAS_number = 79902-63-9 | PubChem = 54454 | DrugBank_Ref = | DrugBank = DB00641 | ChemSpiderID_Ref = | ChemSpiderID = 49179 | UNII_Ref = | UNII = AGG2FN16EV | KEGG_Ref = | KEGG = D00434 | ChEBI_Ref = | ChEBI = 9150 | ChEMBL_Ref = | ChEMBL = 1064 | 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 | 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 = | 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 = | StdInChIKey = RYMZZMVNJRMUDD-HGQWONQESA-N }}