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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C33H34FN2O5.Ca.3H2O
Molecular Weight 1209.388
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATORVASTATIN CALCIUM TRIHYDRATE

SMILES

O.O.O.[Ca++].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.CC(C)C5=C(C(=O)NC6=CC=CC=C6)C(=C(N5CC[C@@H](O)C[C@@H](O)CC([O-])=O)C7=CC=C(F)C=C7)C8=CC=CC=C8

InChI

InChIKey=SHZPNDRIDUBNMH-NIJVSVLQSA-L
InChI=1S/2C33H35FN2O5.Ca.3H2O/c2*1-21(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;;;;/h2*3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40);;3*1H2/q;;+2;;;/p-2/t2*26-,27-;;;;/m11..../s1

HIDE SMILES / InChI

Description

Atorvastatin calcium (LIPITOR®) is a pyrrole and heptanoic acid derivative, a synthetic lipid-lowering agent. Atorvastatin is a selective, competitive inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase. This enzyme catalyzes the conversion of HMG-CoA to mevalonate, an early and rate-limiting step in cholesterol biosynthesis. Atorvastatin is used to reduce serum levels of LDL(low-density lipoprotein)-cholesterol; apolipoprotein B; and triglycerides and to increase serum levels of HDL(high-density lipoprotein)-cholesterol in the treatment of hyperlipidemias and prevention of cardiovascular disease in patients with multiple risk factors.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
14.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
LIPITOR
Primary
LIPITOR

Cmax

ValueDoseCo-administeredAnalytePopulation
33.24 ng/mL
80 mg single, oral
ATORVASTATIN plasma
Homo sapiens
8.8 ng/mL
20 mg single, oral
ATORVASTATIN blood
Homo sapiens
9.52 ng/mL
20 mg single, oral
ATORVASTATIN blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
140.79 ng*h/mL
80 mg single, oral
ATORVASTATIN plasma
Homo sapiens
142.86 ng*h/mL
80 mg single, oral
ATORVASTATIN plasma
Homo sapiens
137.49 ng*h/mL
80 mg single, oral
ATORVASTATIN plasma
Homo sapiens
45 ng × h/mL
20 mg single, oral
ATORVASTATIN blood
Homo sapiens
35.04 ng × h/mL
20 mg single, oral
ATORVASTATIN blood
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.21 h
80 mg single, oral
ATORVASTATIN plasma
Homo sapiens
6.2 h
20 mg single, oral
ATORVASTATIN blood
Homo sapiens
16.57 h
20 mg single, oral
ATORVASTATIN blood
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended starting dose of atorvastatin calcium (LIPITOR®) is 10 or 20 mg once daily. Patients who require a large reduction in LDL(low-density lipoprotein)-cholesterol (more than 45%) may be started at 40 mg once daily. The dosage range of atorvastatin calcium is 10 to 80 mg once daily. Atorvastatin calcium can be administered as a single dose at any time of the day, with or without food. The starting dose and maintenance doses of atorvastatin calcium should be individualized according to patient characteristics such as goal of therapy and response. After initiation and/or upon titration of atorvastatinc calcium, lipid levels should be analyzed within 2 to 4 weeks and dosage adjusted accordingly.
Route of Administration: Oral
In Vitro Use Guide
In vitro, atorvastatin (CI-981) was equipotent as HMG-CoA reductase inhibitor in rat liver, spleen, testis and adrenal tissue (IC50 38.7 nM, 29.5 nM, 36.4, and 100.4 nM, respectively).