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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
Structure of ENT-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
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12433810

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

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Regulation of CYP2B6 and CYP3A expression by hydroxymethylglutaryl coenzyme A inhibitors in primary cultured human hepatocytes.
2002 Dec
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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.
Name Type Language
ENT-ATORVASTATIN
Common Name English
ATORVASTATIN CALCIUM IMPURITY E [EP IMPURITY]
Common Name English
1H-PYRROLE-1-HEPTANOIC ACID, 2-(4-FLUOROPHENYL)-.BETA.,.DELTA.-DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-((PHENYLAMINO)CARBONYL)-, (.BETA.S,.DELTA.S)-
Systematic Name English
3S,5S-ATORVASTATIN
Common Name English
(3S,5S)-7-(2-(4-FLUOROPHENYL)-5-(1-METHYLETHYL)-3-PHENYL-4-(PHENYLCARBAMOYL)-1H-PYRROL-1-YL)-3,5-DIHYDROXYHEPTANOIC ACID
Systematic Name English
Code System Code Type Description
FDA UNII
U2H272PQ8B
Created by admin on Sat Dec 16 05:18:12 GMT 2023 , Edited by admin on Sat Dec 16 05:18:12 GMT 2023
PRIMARY
PUBCHEM
62976
Created by admin on Sat Dec 16 05:18:12 GMT 2023 , Edited by admin on Sat Dec 16 05:18:12 GMT 2023
PRIMARY
CAS
501121-34-2
Created by admin on Sat Dec 16 05:18:12 GMT 2023 , Edited by admin on Sat Dec 16 05:18:12 GMT 2023
PRIMARY