Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H35FN2O5 |
Molecular Weight | 558.6398 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C1=C(C(=O)NC2=CC=CC=C2)C(=C(N1CC[C@@H](O)C[C@H](O)CC(O)=O)C3=CC=C(F)C=C3)C4=CC=CC=C4
InChI
InChIKey=XUKUURHRXDUEBC-SXOMAYOGSA-N
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
(3S,5R)-atorvastatin is a stereoisomer of atorvastatin. Atorvastatin is a synthetic hydroxymethylglutaryl coenzyme A (HMG-CoA) reductase inhibitor. 3R,5R enantiopure form of atorvastatin (Lipitor, Pfizer; since Nov 2011 generic) is used clinically. It reduces levels of total cholesterol, low-density lipoprotein (LDL)-cholesterol, triglyceride and very low-density lipoprotein (VLDL)-cholesterol and increases high-density lipoprotein (HDL)-cholesterol in patients with a wide variety of dyslipidaemias.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26366873 |
11.6 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26366873
30 uM (3S,5R)-atorvastatin induces the expression of drug-metabolizing cytochromes P450 CYP2B6 and CYP3A4 at protein level in primary human hepatocytes.
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SUBSTANCE RECORD