atorvastatin   Click here for help

GtoPdb Ligand ID: 2949

Synonyms: Lipitor®
Approved drug PDB Ligand
atorvastatin is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: The 3S, 5S-Atorvastatin enantiomer is inactive [4]. Atorvastatin is metabolised to form active metabolites atorvastatin lactone (CID 6483036), o-hydroxyatorvastatin (CID 9808225) and p-hydroxyatorvastatin (CID 9851106).

Atorvastatin calcium is found in combination with amlodipine besylate in the drug Caduet®.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 13
Topological polar surface area 111.79
Molecular weight 558.25
XLogP 5.68
No. Lipinski's rules broken 2
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Canonical SMILES OC(CC(CC(=O)O)O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1
Isomeric SMILES O[C@@H](C[C@H](CC(=O)O)O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1
InChI InChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996))
Is prodrug? Yes
Active form o-hydroxyatorvastatinp-hydroxyatorvastatin
IUPAC Name Click here for help
(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid
International Nonproprietary Names Click here for help
INN number INN
7259 atorvastatin
Synonyms Click here for help
Database Links Click here for help
CAS Registry No. 134523-00-5 (source: Scifinder)
ChEMBL Ligand CHEMBL1487
DrugBank Ligand DB01076
DrugCentral Ligand 257
GtoPdb PubChem SID 135649972
PubChem CID 60823
RCSB PDB Ligand 117
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Wikipedia Atorvastatin