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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

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-KAYWLYCHSA-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
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Targets

Primary TargetPharmacologyConditionPotency
14.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
LIPITOR
Primary
LIPITOR
PubMed

PubMed

TitleDatePubMed
Hypertriglyceridemia: a review of clinical relevance and treatment options: focus on cerivastatin.
2001
A comparison of simvastatin and atorvastatin up to maximal recommended doses in a large multicenter randomized clinical trial.
2001
Atorvastatin prevents glomerulosclerosis and renal endothelial dysfunction in hypercholesterolaemic rabbits.
2001
Effects of statins on biomarkers of bone metabolism: a randomised trial.
2001 Apr
Possible short-term amelioration of basilar plaque by high-dose atorvastatin: use of reductase inhibitors for intracranial plaque stabilization.
2001 Apr
Tachyphylaxis in 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors.
2001 Apr 15
Assessing the results: phase 1 hyperlipidemia outcomes in 27 health plans.
2001 Apr 16
Effect of hydroxymethyl glutaryl coenzyme a reductase inhibitor therapy on high sensitive C-reactive protein levels.
2001 Apr 17
Lipid-lowering therapy in acute coronary syndromes.
2001 Apr 4
Effects of atorvastatin on early recurrent ischemic events in acute coronary syndromes: the MIRACL study: a randomized controlled trial.
2001 Apr 4
Effect of atorvastatin on low-density lipoprotein subtypes in patients with different forms of hyperlipoproteinemia and control subjects.
2001 Aug
The effect of aggressive versus standard lipid lowering by atorvastatin on diabetic dyslipidemia: the DALI study: a double-blind, randomized, placebo-controlled trial in patients with type 2 diabetes and diabetic dyslipidemia.
2001 Aug
Heart rate variability after long-term treatment with atorvastatin in hypercholesterolaemic patients with or without coronary artery disease.
2001 Aug
Human breath isoprene and its relation to blood cholesterol levels: new measurements and modeling.
2001 Aug
Effect of niacin and atorvastatin on lipoprotein subclasses in patients with atherogenic dyslipidemia.
2001 Aug 1
Correlation of non-high-density lipoprotein cholesterol with apolipoprotein B: effect of 5 hydroxymethylglutaryl coenzyme A reductase inhibitors on non-high-density lipoprotein cholesterol levels.
2001 Aug 1
Treatment of heterozygous familial hypercholesterolemia: atorvastatin vs simvastatin.
2001 Feb
[Statins and unstable angina: MIRACL].
2001 Feb
Celecoxib-induced cholestatic hepatitis.
2001 Feb 6
Aggressive LDL-cholesterol lowering with atorvastatin results in regression of atherosclerosis.
2001 Feb-Mar
Elevated baseline triglyceride levels modulate effects of HMGCoA reductase inhibitors on plasma lipoproteins.
2001 Jan
[Atorvastatin (Lipitor): a review of its pharmacological and clinical profile].
2001 Jan
[Cost-effectiveness of atorvastatin against simvastatin as hypolipemic treatment in hypercholesterolemic patients in primary care].
2001 Jan
Hypolipidemic effect of NK-104 and other 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors in guinea pigs.
2001 Jan
Efficacy and drug interactions of the new HMG-CoA reductase inhibitors cerivastatin and atorvastatin in CsA-treated renal transplant recipients.
2001 Jan
Effective use of statins to prevent coronary heart disease.
2001 Jan 15
[The role of HDL in the prevention of cardiovascular events].
2001 Jan 21
The effects of converting from simvastatin to atorvastatin on plasminogen activator inhibitor type-1.
2001 Jul
Cerivastatin triggers tumor-specific apoptosis with higher efficacy than lovastatin.
2001 Jul
Prolonged inhibition of cholesterol synthesis by atorvastatin inhibits apo B-100 and triglyceride secretion from HepG2 cells.
2001 Jul
Use of intravascular ultrasound to compare effects of different strategies of lipid-lowering therapy on plaque volume and composition in patients with coronary artery disease.
2001 Jul 24
Statin-stimulated nitric oxide release from endothelium.
2001 Jul-Aug
HMG-CoA reductase inhibitors (statins) characterized as direct inhibitors of P-glycoprotein.
2001 Jun
The effect of atorvastatin on postprandial lipaemia in overweight or obese women homozygous for apo E3.
2001 Jun
Effects of low doses of simvastatin and atorvastatin on high-density lipoprotein cholesterol levels in patients with hypercholesterolemia.
2001 Jun
Is a mechanical or a metabolic approach superior in the treatment of coronary disease? Results of the atorvastatin versus revascularization (AVERT) trial.
2001 Jun
HMG-CoA reductase inhibitors improve endothelial dysfunction in normocholesterolemic hypertension via reduced production of reactive oxygen species.
2001 Jun
Rationale, design, methods and baseline demography of participants of the Anglo-Scandinavian Cardiac Outcomes Trial. ASCOT investigators.
2001 Jun
Effect of atorvastatin on plasminogen activator inhibitor type-1 synthesis in human monocytes/macrophages.
2001 Jun
Growth hormone reduces plasma cholesterol in LDL receptor-deficient mice.
2001 Jun
Efficacy of atorvastatin in achieving National Cholesterol Education Program low-density lipoprotein targets in women with severe dyslipidemia and cardiovascular disease or risk factors for cardiovascular disease: The Women's Atorvastatin Trial on Cholesterol (WATCH).
2001 Jun
Increase in circulating endothelial progenitor cells by statin therapy in patients with stable coronary artery disease.
2001 Jun 19
[Atorvastatin].
2001 Mar
Preclinical and clinical pharmacology of Rosuvastatin, a new 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor.
2001 Mar 8
Effects of atorvastatin on early recurrent ischemic events in acute coronary syndromes. The MIRACL study.
2001 Mar-Apr
A cost-effectiveness model of alternative statins to achieve target LDL-cholesterol levels.
2001 May
Statin induced myopathy does not show up in MIBI scintigraphy.
2001 May
Aggressive versus moderate lipid-lowering therapy in postmenopausal women with hypercholesterolemia: Rationale and design of the Beyond Endorsed Lipid Lowering with EBT Scanning (BELLES) trial.
2001 May
Genetic analysis of digestive physiology using fluorescent phospholipid reporters.
2001 May 18
Cost effectiveness of HMG-CoA reductase inhibition in Canada.
2001 Spring
Patents

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).
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:12:11 UTC 2019
Edited
by admin
on Tue Oct 22 00:12:11 UTC 2019
Record UNII
A0JWA85V8F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ATORVASTATIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ATORVASTATIN [WHO-DD]
Common Name English
ATORVASTATIN [HSDB]
Common Name English
(.BETA.R,.DELTA.R)-2-(P-FLUOROPHENYL)-.BETA.,.DELTA.-DIHYDROXY-5-ISOPROPYL-3-PHENYL-4-(PHENYLCARBAMOYL)PYRROLE-1-HEPTANOIC ACID
Common Name English
1H-PYRROLE-1-HEPTANOIC ACID, 2-(4-FLUOROPHENYL)-.BETA.,.DELTA.-DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-((PHENYLAMINO)CARBONYL)-, (R-(R*,R*))-
Common Name English
ATORVASTATIN [MI]
Common Name English
ATORVASTATIN [INN]
Common Name English
ATORVASTATIN [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QC10BX03
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
WHO-ATC C10AA05
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
WHO-VATC QC10AA05
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
WHO-ATC C10BX08
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
LIVERTOX 72
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
NDF-RT N0000175589
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
NCI_THESAURUS C1655
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
WHO-ATC C10BX11
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
WHO-ATC C10BA05
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
WHO-ATC C10BX03
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
WHO-ATC C10BX06
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
WHO-VATC QC10BA05
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
WHO-ATC C10BX15
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
NDF-RT N0000000121
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
WHO-ATC C10BX12
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL1487
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
IUPHAR
2949
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
INN
7259
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
RXCUI
83367
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB01076
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
NCI_THESAURUS
C61527
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
MERCK INDEX
M2125
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY Merck Index
PUBCHEM
60823
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
MESH
C065179
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
LactMed
134523-00-5
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
HSDB
134523-00-5
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
CAS
134523-00-5
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
EVMPD
SUB05600MIG
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
WIKIPEDIA
Atorvastatin
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
EPA CompTox
134523-00-5
Created by admin on Tue Oct 22 00:12:11 UTC 2019 , Edited by admin on Tue Oct 22 00:12:11 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
PARENT -> SALT/SOLVATE
TRANSPORTER -> SUBSTRATE
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC HMG-CoA REDUCTASE INHIBITORY ACTIVITY

Biological Half-life PHARMACOKINETIC