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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 ATORVASTATIN, (3S,5R)-

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

HIDE SMILES / InChI

Molecular Formula C33H35FN2O5
Molecular Weight 558.6398
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

(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

Targets

Primary TargetPharmacologyConditionPotency
11.6 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
30 uM (3S,5R)-atorvastatin induces the expression of drug-metabolizing cytochromes P450 CYP2B6 and CYP3A4 at protein level in primary human hepatocytes.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:42:27 GMT 2023
Edited
by admin
on Sat Dec 16 05:42:27 GMT 2023
Record UNII
W6MO59C0CE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ATORVASTATIN, (3S,5R)-
Common Name English
7-(2-(4-FLUOROPHENYL)-5-ISOPROPYL-3-PHENYL-4-(PHENYLCARBAMOYL)-1H-PYRROL-1-YL)-3,5-DIHYDROXYHEPTANOIC ACID, (3S,5R)-
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.R)-
Common Name English
Code System Code Type Description
PUBCHEM
6093359
Created by admin on Sat Dec 16 05:42:27 GMT 2023 , Edited by admin on Sat Dec 16 05:42:27 GMT 2023
PRIMARY
CAS
887324-52-9
Created by admin on Sat Dec 16 05:42:27 GMT 2023 , Edited by admin on Sat Dec 16 05:42:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID80237276
Created by admin on Sat Dec 16 05:42:27 GMT 2023 , Edited by admin on Sat Dec 16 05:42:27 GMT 2023
PRIMARY
FDA UNII
W6MO59C0CE
Created by admin on Sat Dec 16 05:42:27 GMT 2023 , Edited by admin on Sat Dec 16 05:42:27 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
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