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Details

Stereochemistry RACEMIC
Molecular Formula C33H35FN2O5
Molecular Weight 558.6398
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATORVASTATIN, (±)-

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-SVBPBHIXSA-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-/m0/s1

HIDE SMILES / InChI

Description

Ent-atorvastatin (3S,5S-atorvastatin) is impurity and inactive enantiomer of lipid-lowering agent Atorvastatin.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Freshly isolated hepatocytes were prepared from two different rat livers and placed into primary culture. Forty-eight hours after plating, the cultures were incubated with Williams’ Medium E alone (UT), or containing 0.1% DMSO (vehicle control), 3 x 10_5 M of the active (Atorvastatin) or inactive (Ent-atorvastatin) enantiomer of atorvastatin (in DMSO). Twenty-four hours after treatment, hepatocytes were harvested for the preparation of total RNA, followed by analysis of CYP1A1, CYP2B, CYP3A, CYP4A, and HMG-CoA reductase (HMGRed) mRNA levels by Northern blot hybridization. After initial hybridization of membranes with cDNA probe, blots were rehybridized with a cDNA to 7S RNA, to permit normalization for loading and transfer among samples.