simvastatin   Click here for help

GtoPdb Ligand ID: 2955

Synonyms: MK-733 | Zocor®
Approved drug
simvastatin is an approved drug (FDA (1991), EMA (2013))
Compound class: Synthetic organic
Comment: Simvastatin is a statin class anti-dyslipidemia drug. It is synthetically derived from a fermantation product from Aspergillus terreus.
Simvastatin is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 72.83
Molecular weight 418.27
XLogP 4.78
No. Lipinski's rules broken 0
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Isomeric SMILES CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)(C)C
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1991), EMA (2013))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
[(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
International Nonproprietary Names Click here for help
INN number INN
6147 simvastatin
Synonyms Click here for help
MK-733 | Zocor®
Database Links Click here for help
CAS Registry No. 79902-63-9 (source: Scifinder)
ChEMBL Ligand CHEMBL1064
DrugBank Ligand DB00641
DrugCentral Ligand 2445
GtoPdb PubChem SID 135651045
PubChem CID 54454
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UniChem Compound Search for chemical match using the InChIKey RYMZZMVNJRMUDD-HGQWONQESA-N
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Wikipedia Simvastatin

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Simvastatin (links to external site)
Cat. No. 1965