Compound: simvastatin
SMILES: O=C1O[C@@H](C[C@H](C1)O)CC[C@@H]2[C@@H]3C(C=C[C@@H]2C)=C[C@H](C)C[C@@H]3OC(=O)C(CC)(C)C
InChIKey: RYMZZMVNJRMUDD-HGQWONQESA-N
Synonyms: simvastatin, 79902-63-9, Zocor, Synvinolin, MK-733, Sinvacor, Denan, Lipex, Simvastatine, Sivastin, Lodales, Cholestat, Simvastatina, Colemin, Medipo, Simovil, Labistatin, Simvastatinum, Velostatin, Nivelipol, Rechol, (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, MK-0733, Simvastatinum [Latin], DTXSID0023581, AGG2FN16EV, MK733, 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, MK 733, NSC-758706, C10AA01, (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, CHEBI:9150, DTXCID103581, Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, NSC633782, [(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, Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, Simvastatinum (Latin), Butanoic acid, 2,2-dimethyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1alpha,3alpha,7beta,8beta(2S*,4S*),8abeta))-, Lacersa, Ranzolont, Simvador, Zocor heart-pro, ((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, 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, FLOLIPID, RefChem:6225, (1S-(1alpha,3alpha,7beta,8beta(2S*,4S*),8abeta))-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl 2,2-dimethylbutanoate, 616-751-8, Pantok, Zocord, Lipovas, Zorced, Simvastatin lactone, Simvastatin (Zocor), Simcard, Simvacor, Simvoget, Simlup, MFCD00072007, Statin, (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, Coledis, Corolin, Rendapid, Vasotenal, C25H38O5, A1BYZ, Simvastatine [French], Simvastatina [Spanish], [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-tetrahydropyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate, Zosta, Simvast CR, DRG-0320, SMR000718785, MK 0733, CCRIS 7558, Zocor (TN), HSDB 7208, Simvastatin & Primycin, SR-05000001894, UNII-AGG2FN16EV, L 644128-000U, BRN 4768037, Kolestevan, Lipinorm, Modutrol, Simvotin, Sinvascor, Valemia, Eucor, Synvinolin;, Velastatin;, Liponorm;, Sinvacor;, Sivastin;, Colemin;, Lodales;, Nor-Vastina, Simvastatin CRS, Medipo;, Pantok;, Denan;, Lipex;, Zocor;, simvastatin predrug, (+)-Simvastatin, NCGC00016940-01, inactive simvastatin, 8-[2-((2R,4R)-4-hydroxy-6-oxo(2H-3,4,5-trihydropyran-2-yl))ethyl](1S,7S,8S,3R, 8aR)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthyl 2,2-dimethylbutanoate, Simvastatin [USAN:USP:INN:BAN], TNP00259, Prestwick_171, CAS-79902-63-9, KS-1113, Simvastatin (Zocor)?, Simvastatin (Standard), Spectrum_001717, SpecPlus_000895, SIMVASTATIN [MI], Prestwick0_000865, Prestwick1_000865, Prestwick2_000865, Prestwick3_000865, Spectrum2_001671, Spectrum3_000669, Spectrum4_000632, Spectrum5_001428, SIMVASTATIN [INN], SIMVASTATIN [JAN], SIMVASTATIN [HSDB], SIMVASTATIN [USAN], SIMVASTATIN [VANDF], SCHEMBL2471, CHEMBL1064, SIMVASTATIN [MART.], BSPBio_000909, BSPBio_002337, KBioGR_001244, KBioSS_002197, SIMVASTATIN [USP-RS], SIMVASTATIN [WHO-DD], MLS001304029, MLS001333077, MLS001333078, MLS002154038, MLS006011866, BIDD:GT0769, DivK1c_006991, SPECTRUM1504236, SPBio_001881, SPBio_002830, BPBio1_001001, GTPL2955, orb1310385, orb3025100, Simvastatin (JP18/USP/INN), Simvastatin, analytical standard, Simvastatin - Bio-X trade mark, BCBcMAP01_000007, KBio1_001935, KBio2_002197, KBio2_004765, KBio2_007333, KBio3_001557, RYMZZMVNJRMUDD-HGQWONQESA-, SIMVASTATIN [ORANGE BOOK], GLXC-06021, HMS1570N11, HMS1922H13, HMS2089D12, HMS2093E06, HMS2097N11, HMS2231N22, HMS3259B12, HMS3412P08, HMS3676P08, HMS3714N11, HMS3884G10, Pharmakon1600-01504236, SIMVASTATIN [EP MONOGRAPH], SIMCOR COMPONENT SIMVASTATIN, SIMVASTATIN [USP MONOGRAPH], BUTANOIC ACID, 2,2-DIMETHYL-, 1,2,3,7,8,8A-HEXAHYDRO-3,7-DIMETHYL-8-(2-(TETRAHYDRO-4-HYDROXY-6-OXO-2H-PYRAN-2-YL)ETHYL)-1-NAPHTHALENYL ESTER, (1S-(1.ALPHA.,3.ALPHA.,7.BETA.,8.BETA.(2S*,4S*),8A.BETA.))-, MSK10236, VYTORIN COMPONENT SIMVASTATIN, Tox21_110696, Tox21_300400, BBL024390, BDBM50139181, CCG-39069, EBC-00672, HY-17502R, NSC758706, s1792, SBB080618, STK801938, AKOS005111006, AKOS015842733, Simvastatin, >=97% (HPLC), solid, Tox21_110696_1, AC-1530, DB00641, FS27832, NC00719, NSC 758706, NSC-633782, MRF-0000729, NCGC00017324-01, NCGC00017324-02, NCGC00017324-03, NCGC00017324-04, NCGC00017324-05, NCGC00017324-07, NCGC00017324-08, NCGC00017324-09, NCGC00254418-01, 2,2-Dimethylbutanoic acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, BS164407, HY-17502, ST057168, SY002874, SBI-0206773.P001, Simvastatin 100 microg/mL in Acetonitrile, NS00008782, S0509, EN300-52503, D00434, M03997, AB00053395-07, AB00053395-08, AB00053395-10, AB00053395_11, AB00053395_13, Q670131, SR-05000001894-1, SR-05000001894-2, BRD-K22134346-001-05-8, BRD-K22134346-001-11-6, BRD-K22134346-001-15-7, BRD-K22134346-001-21-5, BRD-K22134346-001-22-3, BRD-K22134346-001-24-9, Z754918914, Simvastatin, British Pharmacopoeia (BP) Reference Standard, Simvastatin, European Pharmacopoeia (EP) Reference Standard, Simvastatin, United States Pharmacopeia (USP) Reference Standard, Simvastatin, Pharmaceutical Secondary Standard; Certified Reference Material, Simvastatin for peak identification, European Pharmacopoeia (EP) Reference Standard, (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxo-tetrahydro-2H-2-pyranyl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl 2,2-Dimethylbutanoate, (1S,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, InChI=1/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
Theoretical properties:
molecular_formula: C25H38O5
molecular_weight: 418.6 g/mol
exact_mass: 418.27192431 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 7
heavy_atom_count: 30
topological_polar_surface_area: 72.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off-white crystalline powder from n-butyl chloride + hexane
color: White to off-white crystalline powder from n-butyl chloride + hexane
melting_point: 135-138 °C
solubility: Insoluble
Descriptions:
{"pubchem": "Simvastatin is a member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug. It has a role as a ferroptosis inducer, a geroprotector, an EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor, a prodrug and an EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor. It is a member of hexahydronaphthalenes, a delta-lactone, a fatty acid ester and a statin (semi-synthetic). It is functionally related to a lovastatin.", "chebi": "A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.", "chembl": "SIMVASTATIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "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.\nCommon 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.\nSimvastatin 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 2023, it was the 22nd most commonly prescribed medication in the United States, with more than 24 million prescriptions."}