Responsive image

Common name


Simvastatin

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


[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)C(C)(C)CC

Compound class


Anticholesteremic Agents; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypolipidemic Agents; Drugs Used in Diabetes; Alimentary Tract and Metabolism; HMG CoA Reductase Inhibitors; Lipid Modifying Agents, Plain; Lipid Modifying Agents; Cardiovascular System; Blood Glucose Lowering Drugs, Excl. Insulins; Cytochrome P-450 CYP2C9 Inhibitors; Cytochrome P-450 CYP2C8 Inhibitors; Cytochrome P-450 CYP2C9 Inducers; Cytochrome P-450 CYP2C19 Inducers; Cytochrome P-450 CYP2C8 Inducers; Cytochrome P-450 CYP2B6 Inducers; Cytochrome P-450 CYP2B6 Inhibitors; CYP2B6 Inhibitors (strong); CYP2D6 Inducers; CYP2D6 Inducers (strong); CYP3A4 Inhibitors; Combined Inhibitors of CYP3A4 and P-glycoprotein;

Therapeutic area


For the treatment of hypercholesterolemia and for the reduction in the risk of cardiac heart disease mortality and cardiovascular events. It can also be used in adolescent patients for the treatment of heterozygous familial hypercholesterolemia.

Common name


Simvastatin

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


[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)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

FORMULA


C25H38O5

Responsive image

Common name


Simvastatin

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

Molecular weight


418.566

clogP


3.765

clogS


-3.562

HBond Acceptor


5

HBond Donor


1

Total Polar
Surface Area


72.83

Number of Rings


3

Rotatable Bond


7

Drug ID Common name Structure CAS SMILE Frequency
FDBF00007 propane Responsive image C(C)C 0.2412
FDBF00115 2-methylbutane Responsive image C(C)(C)CC 0.0103
FDBF00455 [(1S,3R,7S,8S,8aR)-3,7,8-trimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] formate Responsive image CC1C2C(=CC(CC2OC=O)C)C=CC1C 0.0007
FDBF00456 (4R,6R)-4-hydroxy-6-methyl-tetrahydropyran-2-one Responsive image CC1OC(=O)CC(C1)O 0.0007
FDBF00458 [(1S,3R,7S,8S,8aR)-8-ethyl-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] formate Responsive image CCC1C2C(=CC(CC2OC=O)C)C=CC1C 0.0007
FDBF00460 (4R,6R)-6-ethyl-4-hydroxy-tetrahydropyran-2-one Responsive image C(C)C1OC(=O)CC(C1)O 0.0007
FDBF00461 [(1S,3R,7R,8aR)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] formate Responsive image O(C=O)C1C2CC(C=CC2=CC(C1)C)C 0.0007
FDBF00462 (4R)-4-hydroxytetrahydropyran-2-one Responsive image O1CCC(CC1=O)O 0.0007
FDBF01465 [(1S,3R,7R,8aR)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2-methylpropanoate Responsive image O(C(=O)C(C)C)C1C2CC(C=CC2=CC(C1)C)C 0.0003
FDBF01466 [(1S,3R,7S,8S,8aR)-3,7,8-trimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2-methylpropanoate Responsive image CC1C2C(=CC(CC2OC(=O)C(C)C)C)C=CC1C 0.0003
10 , 2