Structure via PubChem · Public domain (PubChem)
simvastatin
Sign in to saveAlso 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.
OverviewAI-generated
Simvastatin is a chemical compound with the formula C₂₅H₃₈O₅. It has a mass of 418.272 and a weight of 418.6. The substance possesses a charge of 0, an xlogp value of 4.7, and a topological polar surface area of 72.8. Its molecular structure includes one hydrogen bond donor and five hydrogen bond acceptors.
The defined daily dose for simvastatin is 30. The compound is referenced by 462 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1991
- Admin. routes
- oral
- Indications
- chronic obstructive pulmonary disease, Disorder of lipid metabolism, Hypercholesterolemia, atrial fibrillation
via ChEMBL · EBI
Research
13,209 papers- Simvastatin-Incorporated Drug Delivery Systems for Bone Regeneration.ACS biomaterials science & engineering · 2021
- Repurposing simvastatin in cancer treatment: an updated review on pharmacological and nanotechnological aspects.Naunyn-Schmiedeberg's archives of pharmacology · 2024
- Niacin extended-release/simvastatin.Drugs · 2008
- Simvastatin interactions with other drugs.Expert opinion on drug safety · 2012
- Ezetimibe/Simvastatin: a review of its use in the management of hypercholesterolemia.American journal of cardiovascular drugs : drugs, devices, and other interventions · 2004
via PubMed
Wikidata facts
- Subclass of
- statin
- Has part
- carbon
- Mass
- 418.272
- Has use
- medication
Show 11 more facts
- significant drug interaction
- posaconazole
- chemical formula
- C₂₅H₃₈O₅
- medical condition treated
- lipedema
- isomeric 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
- canonical SMILES
- CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C
- World Health Organisation international non-proprietary name
- simvastatin
- Commons category
- Simvastatin
- defined daily dose
- 30
- subject has role
- essential medicine
- physically interacts with
- 3-hydroxy-3-methylglutaryl-CoA reductase
- legal status (medicine)
- boxed warning
Sources (9)
via Wikidata · CC0
~14 min read
Encyclopedic overview
12 sectionsContents
- 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 }}
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.
Excerpted from Wikipedia’s “simvastatin” article, available under the CC BY-SA 4.0 licence.