U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28FN3O6S
Molecular Weight 481.538
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ROSUVASTATIN

SMILES

CC(C)C1=C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)C(=NC(=N1)N(C)S(C)(=O)=O)C2=CC=C(F)C=C2

InChI

InChIKey=BPRHUIZQVSMCRT-VEUZHWNKSA-N
InChI=1S/C22H28FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32/h5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30)/b10-9+/t16-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H28FN3O6S
Molecular Weight 481.538
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

CRESTOR (rosuvastatin calcium) is an inhibitor of HMG-CoA reductase. It has been widely launched for the treatment of patients with dyslipidaemia and has also been approved in the US and EU to slow the progression of atherosclerosis.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
A new HMG-CoA reductase inhibitor, rosuvastatin, exerts anti-inflammatory effects on the microvascular endothelium: the role of mevalonic acid.
2001 Jun
Preclinical and clinical pharmacology of Rosuvastatin, a new 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor.
2001 Mar 8
Rosuvastatin, a new HMG-CoA reductase inhibitor, upregulates endothelial nitric oxide synthase and protects from ischemic stroke in mice.
2002 Jun 28
Direct vascular and cardioprotective effects of rosuvastatin, a new HMG-CoA reductase inhibitor.
2002 Sep 18
Comparison of the efficacy and safety of rosuvastatin versus atorvastatin, simvastatin, and pravastatin across doses (STELLAR* Trial).
2003 Jul 15
Beneficial effects of rosuvastatin alone and in combination with extended-release niacin in patients with a combined hyperlipidemia and low high-density lipoprotein cholesterol levels.
2003 Jun 1
The statin wars.
2003 Nov 1
The statin wars: why AstraZeneca must retreat.
2003 Oct 25
Rosuvastatin-induced arrest in progression of renal disease.
2004
Rosuvastatin alone or with extended-release niacin: a new therapeutic option for patients with combined hyperlipidemia.
2004 Fall
Rosuvastatin treatment reverses impaired coronary artery vasodilation in fructose-fed, insulin-resistant rats.
2004 Jul
Effects of switching statins on lipid and apolipoprotein ratios in the MERCURY I study.
2005 Apr 20
Bile salt export pump (BSEP/ABCB11) can transport a nonbile acid substrate, pravastatin.
2005 Aug
Aggravation of focal cerebral ischemia by tissue plasminogen activator is reversed by 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor but does not depend on endothelial NO synthase.
2005 Feb
Comparison of rosuvastatin with atorvastatin, simvastatin and pravastatin in achieving cholesterol goals and improving plasma lipids in hypercholesterolaemic patients with or without the metabolic syndrome in the MERCURY I trial.
2005 Jul
Chronic treatment with rosuvastatin modulates nitric oxide synthase expression and reduces ischemia-reperfusion injury in rat hearts.
2005 Jun 1
Rosuvastatin, but not simvastatin, provides end-organ protection in stroke-prone rats by antiinflammatory effects.
2005 Mar
Binding thermodynamics of statins to HMG-CoA reductase.
2005 Sep 6
Effect of very high-intensity statin therapy on regression of coronary atherosclerosis: the ASTEROID trial.
2006 Apr 5
Rosuvastatin treatment protects against nitrate-induced oxidative stress in eNOS knockout mice: implication of the NAD(P)H oxidase pathway.
2006 Jun
Statin-associated myasthenia gravis: report of 4 cases and review of the literature.
2006 Mar
Drug and bile acid transporters in rosuvastatin hepatic uptake: function, expression, and pharmacogenetics.
2006 May
An overview of statin-associated proteinuria.
2006 May
Design and synthesis of hepatoselective, pyrrole-based HMG-CoA reductase inhibitors.
2007 Aug 15
Statin treatment and 3' polyadenylation of eNOS mRNA.
2007 Dec
Myopathy caused by a combination rosuvastatin and fenofibrate.
2007 Feb
McArdle disease with rhabdomyolysis induced by rosuvastatin: case report.
2007 Sep
Rosuvastatin protects against oxidative stress and DNA damage in vitro via upregulation of glutathione synthesis.
2008 Aug
Statin therapy alters the relationship between apolipoprotein B and low-density lipoprotein cholesterol and non-high-density lipoprotein cholesterol targets in high-risk patients: the MERCURY II (Measuring Effective Reductions in Cholesterol Using Rosuvastatin) trial.
2008 Aug 19
In-vivo effects of simvastatin and rosuvastatin on global gene expression in peripheral blood leucocytes in a human inflammation model.
2008 Feb
Vascular and neural dysfunction in Zucker diabetic fatty rats: a difficult condition to reverse.
2008 Jan
Rationale and design of the carotid plaque in human for all evaluations with aggressive rosuvastatin therapy (CHALLENGER trial): evaluation by magnetic resonance imaging.
2009 Jan
Rosuvastatin prevents endothelial cell death and reduces atherosclerotic lesion formation in ApoE-deficient mice.
2009 Jan
Rosuvastatin-associated adverse effects and drug-drug interactions in the clinical setting of dyslipidemia.
2010
WT-1 mRNA expression is modulated by nitric oxide availability and Hsp70 interaction after neonatal unilateral ureteral obstruction.
2010 Dec
Functional characterization of mouse organic anion transporting peptide 1a4 in the uptake and efflux of drugs across the blood-brain barrier.
2010 Jan
Rosuvastatin in the prevention of stroke among men and women with elevated levels of C-reactive protein: justification for the Use of Statins in Prevention: an Intervention Trial Evaluating Rosuvastatin (JUPITER).
2010 Jan 5
Biliary efflux transporters involved in the clearance of rosuvastatin in sandwich culture of primary rat hepatocytes.
2010 Mar
Effect of rosuvastatin on cholestasis-induced hepatic injury in rat livers.
2010 Mar-Apr
Case report. Hyperlipoproteinaemia(a): which is the optimal therapy? A case report.
2010 Oct
Rosuvastatin induces apoptosis in CD4(+)CD28 (null) T cells in patients with acute coronary syndromes.
2011 Feb
Rosuvastatin attenuates the elevation in blood pressure induced by overexpression of human C-reactive protein.
2011 Jul
Rosuvastatin induces apoptosis in cultured human papillary thyroid cancer cells.
2011 Jul
Rosuvastatin prevents myocardial necrosis in an experimental model of acute myocardial infarction.
2011 May
Renal toxicity of lisinopril and rosuvastatin, alone and in combination, in Wistar rats.
2011 Oct
Detection of statin cytotoxicity is increased in cells expressing the OATP1B1 transporter.
2013 Jul
ATP-dependent transport of statins by human and rat MRP2/Mrp2.
2013 Jun 1
Statins alter the hepatobiliary transport of unconjugated and conjugated bilirubin in sandwich-cultured rat hepatocytes.
2014 Sep
Patents

Sample Use Guides

In Vivo Use Guide
The dose range for CRESTOR (rosuvastatin calcium) is 5 to 40 mg orally once daily. The usual starting dose is 10-20 mg.
Route of Administration: Oral
In Vitro Use Guide
HUVECs treated with 30 mM glucose were used to simulate high-glucose conditions, and rosuvastatin concentrations ranging from 0.1 to 10 nM were used.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:06:05 UTC 2019
Edited
by admin
on Tue Oct 22 00:06:05 UTC 2019
Record UNII
413KH5ZJ73
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROSUVASTATIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ROSUVASTATIN [HSDB]
Common Name English
ZD4522
Code English
ROSUVASTATIN [MI]
Common Name English
6-HEPTENOIC ACID, 7-(4-(4-FLUOROPHENYL)-6-(1-METHYLETHYL)-2-(METHYL(METHYLSULFONYL)AMINO)-5-PYRIMIDINYL)-3,5-DIHYDROXY-, (3R,5S,6E)-
Common Name English
(3R,5S,6E)-7-(4-(4-FLUOROPHENYL)-6-ISOPROPYL-2-(METHYL(METHYLSULFONYL)AMINO)PYRIMIDIN-5-YL)-3,5-DIHYDROXYHEPT-6-ENOIC ACID
Systematic Name English
ROSUVASTATIN [WHO-DD]
Common Name English
ROSUVASTATIN [VANDF]
Common Name English
CRESTON
Brand Name English
ROSUVASTATIN [INN]
Common Name English
X-PLENDED
Common Name English
ZD-4522
Code English
Classification Tree Code System Code
WHO-ATC C10BX09
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-ATC C10BX14
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-VATC QC10BX05
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-ATC C10BX07
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-ATC C10AA07
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
NDF-RT N0000000121
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
FDA ORPHAN DRUG 420513
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-ATC A10BH52
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-ATC C10BA06
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-VATC QC10AA07
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-ATC C10BX10
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
NCI_THESAURUS C1655
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-ATC C10BX13
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
LIVERTOX 864
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-ATC C10BX05
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
NDF-RT N0000175589
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
WHO-VATC QC10BA06
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C66523
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
EPA CompTox
287714-41-4
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
WIKIPEDIA
ROSUVASTATIN
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
PUBCHEM
446157
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
MESH
C422923
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
RXCUI
301542
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY RxNorm
CAS
287714-41-4
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
ChEMBL
CHEMBL1496
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
EVMPD
SUB20634
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
DRUG BANK
DB01098
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
MERCK INDEX
M9672
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY Merck Index
LactMed
287714-41-4
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
IUPHAR
2954
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
INN
8021
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
HSDB
287714-41-4
Created by admin on Tue Oct 22 00:06:05 UTC 2019 , Edited by admin on Tue Oct 22 00:06:05 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Km
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE LESS ACTIVE -> PARENT
N-desmethyl rosuvastatin has approximately one-sixth to one-half the HMG-CoA reductase inhibitory activity of the parent compound.
METABOLITE LESS ACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
MAXIMUM TOLERATED DOSE TOXICITY
Tmax PHARMACOKINETIC