Identification

Name
Rosuvastatin
Accession Number
DB01098  (APRD00546)
Type
Small Molecule
Groups
Approved
Description

Rosuvastatin is an antilipemic agent that competitively inhibits hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase. HMG-CoA reducuase catalyzes the conversion of HMG-CoA to mevalonic acid, the rate-limiting step in cholesterol biosynthesis. Rosuvastatin belongs to a class of medications called statins and is used to reduce plasma cholesterol levels and prevent cardiovascular disease.

Structure
Thumb
Synonyms
  • (3R,5S,6E)-7-(4-(4-fluorophenyl)-6-(1-methylethyl)-2-(ethyl(methylsulfonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-6-heptenoic acid
  • (3R,5S,6E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoic acid
  • Rosuvastatin
  • Rosuvastatina
External IDs
ZD-4522 / ZD4522
Product Ingredients
IngredientUNIICASInChI Key
Rosuvastatin calcium83MVU38M7Q147098-20-2LALFOYNTGMUKGG-JGMJEEPBSA-L
Rosuvastatin zinc70VE4E19Z7953412-08-3KUQHZGJLQWUFPU-BGRFNVSISA-L
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act RosuvastatinTablet20 mgOralActavis Pharma Company2012-03-16Not applicableCanada
Act RosuvastatinTablet5 mgOralActavis Pharma Company2012-03-16Not applicableCanada
Act RosuvastatinTablet40 mgOralActavis Pharma Company2012-03-16Not applicableCanada
Act RosuvastatinTablet10 mgOralActavis Pharma Company2012-03-16Not applicableCanada
CrestorTablet, film coated5 mg/1Oralbryant ranch prepack2003-08-18Not applicableUs63629 437220180913 8702 iqzde4
CrestorTablet, film coated5 mg/1OralCardinal Health2010-12-012018-03-31Us55154 692320180913 8702 plemsz
CrestorTablet, film coated5 mg/1OralRebel Distributors2005-06-22Not applicableUs00310 0755 90 nlmimage10 891344fa
CrestorTablet, film coated5 mg/1OralAstraZeneca Pharmaceuticals LP2003-08-18Not applicableUs0310 075520180907 15195 vgonc
CrestorTablet, film coated20 mg/1OralMed Health Pharma LLC.2011-02-222012-04-05Us
CrestorTablet, film coated10 mg/1OralAphena Pharma Solutions Tennessee, Inc.2003-08-18Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ach-rosuvastatinTablet5 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Ach-rosuvastatinTablet20 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Ach-rosuvastatinTablet10 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Ach-rosuvastatinTablet40 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Apo-rosuvastatinTablet5 mgOralApotex Corporation2012-04-02Not applicableCanada
Apo-rosuvastatinTablet20 mgOralApotex Corporation2012-04-02Not applicableCanada
Apo-rosuvastatinTablet10 mgOralApotex Corporation2012-04-02Not applicableCanada
Apo-rosuvastatinTablet40 mgOralApotex Corporation2012-04-02Not applicableCanada
Auro-rosuvastatinTablet5 mgOralAuro Pharma Inc2015-11-30Not applicableCanada
Auro-rosuvastatinTablet20 mgOralAuro Pharma Inc2015-11-30Not applicableCanada
International/Other Brands
Astende (Lazar (Argentina)) / Cirantan (AstraZeneca (Netherlands)) / Cresadex (Drugtech (Chile)) / Provisacor (AstraZeneca (Italy, Netherlands) ) / Razel (Glenmark (India)) / Rosedex (Roux-Ocefa (Argentina)) / Rosimol (Sandoz (Argentina)) / Rosumed (Labomed (Chile)) / Rosustatin (Montpellier (Argentina)) / Rosuvas (Ranbaxy (India)) / Rosuvast (Bago (Argentina)) / Rosvel (Laboratorios Chile (Chile)) / Rovartal (Roemmers (Argentina)) / Simestat (Simesa (Italy)) / Sinlip (Gador (Argentina)) / Visacor (AstraZeneca (Portugal)) / Vivacor (AstraZeneca (Brazil))
Categories
UNII
413KH5ZJ73
CAS number
287714-41-4
Weight
Average: 481.538
Monoisotopic: 481.168284538
Chemical Formula
C22H28FN3O6S
InChI Key
BPRHUIZQVSMCRT-VEUZHWNKSA-N
InChI
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
IUPAC Name
(3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid
SMILES
CC(C)C1=NC(=NC(C2=CC=C(F)C=C2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(=O)O)N(C)S(C)(=O)=O

Pharmacology

Indication

Used as an adjunct to dietary therapy to treat primary hyperlipidemia (heterozygous familial and nonfamilial), mixed dyslipidemia and hypertriglyceridemia. Also indicated for homozygous familial hypercholesterolemia as an adjunct to other lipid-lowering therapies or when other such therapies are not available. Furthermore, it is used to slow the progression of atherosclerosis and for primary prevention of cardiovascular disease.

Associated Conditions
Pharmacodynamics

Rosuvastatin is a synthetic, enantiomerically pure antilipemic agent. It is used to lower total cholesterol, low density lipoprotein-cholesterol (LDL-C), apolipoprotein B (apoB), non-high density lipoprotein-cholesterol (non-HDL-C), and trigleride (TG) plasma concentrations while increasing HDL-C concentrations. High LDL-C, low HDL-C and high TG concentrations in the plasma are associated with increased risk of atherosclerosis and cardiovascular disease. The total cholesterol to HDL-C ratio is a strong predictor of coronary artery disease and high ratios are associated with higher risk of disease. Increased levels of HDL-C are associated with lower cardiovascular risk. By decreasing LDL-C and TG and increasing HDL-C, rosuvastatin reduces the risk of cardiovascular morbidity and mortality.

Mechanism of action

Rosuvastatin is a competitive inhibitor of HMG-CoA reductase. HMG-CoA reductase catalyzes the conversion of HMG-CoA to mevalonate, an early rate-limiting step in cholesterol biosynthesis. Rosuvastatin acts primarily in the liver. Decreased hepatic cholesterol concentrations stimulate the upregulation of hepatic low density lipoprotein (LDL) receptors which increases hepatic uptake of LDL. Rosuvastatin also inhibits hepatic synthesis of very low density lipoprotein (VLDL). The overall effect is a decrease in plasma LDL and VLDL. In vitro and in vivo animal studies also demonstrate that rosuvastatin exerts vasculoprotective effects independent of its lipid-lowering properties. Rosuvastatin exerts an anti-inflammatory effect on rat mesenteric microvascular endothelium by attenuating leukocyte rolling, adherence and transmigration (PMID: 11375257). The drug also modulates nitric oxide synthase (NOS) expression and reduces ischemic-reperfusion injuries in rat hearts (PMID: 15914111). Rosuvastatin increases the bioavailability of nitric oxide (PMID: 11375257, 12031849, 15914111) by upregulating NOS (PMID: 12354446) and by increasing the stability of NOS through post-transcriptional polyadenylation (PMID: 17916773). It is unclear as to how rosuvastatin brings about these effects though they may be due to decreased concentrations of mevalonic acid.

TargetActionsOrganism
A3-hydroxy-3-methylglutaryl-coenzyme A reductase
inhibitor
Human
Absorption

Bioavailability is approximately 20%. Peak plasma concentrations were reached 3 to 5 hours following oral dosing. Both Cmax and AUC increased in approximate proportion to CRESTOR dose. Food has no effect on the AUC of rosuvastatin.

Volume of distribution
  • 134 L [steady-state]
Protein binding

88% bound to plasma proteins (mostly albumin). Binding is reversible and independent of plasma concentrations.

Metabolism

Not extensively metabolized. Only ~10% is excreted as metabolite. Cytochrome P450 (CYP) 2C9 is primarily responsible for the formation of rosuvastatin's major metabolite, N-desmethylrosuvastatin. N-desmethylrosuvastatin has approximately 50% of the pharmacological activity of its parent compound in vitro. Rosuvastatin clearance is not dependent on metabolism by cytochrome P450 3A4 to a clinically significant extent. Rosuvastatin accounts for greater than 90% of the pharmacologic action. Inhibitors of CYP2C9 increase the AUC by less than 2-fold. This interaction does not appear to be clinically significant.

Route of elimination

Rosuvastatin is not extensively metabolized; approximately 10% of a radiolabeled dose is recovered as metabolite. Following oral administration, rosuvastatin and its metabolites are primarily excreted in the feces (90%). After an intravenous dose, approximately 28% of total body clearance was via the renal route, and 72% by the hepatic route.

Half life

19 hours

Clearance
Not Available
Toxicity

Generally well-tolerated. Side effects may include myalgia, constipation, asthenia, abdominal pain, and nausea. Other possible side effects include myotoxicity (myopathy, myositis, rhabdomyolysis) and hepatotoxicity. To avoid toxicity in Asian patients, lower doses should be considered. Pharmacokinetic studies show an approximately two-fold increase in peak plasma concentration and AUC in Asian patients (Philippino, Chinese, Japanese, Korean, Vietnamese, or Asian-Indian descent) compared to Caucasians patients.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Rosuvastatin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Kinesin-like protein KIF6---(C;C) / (C;T)C AlleleEffect Directly StudiedPatients with this genotype have a greater reduction in risk of a major cardiovascular event with high dose rosuvastatin.Details
3-hydroxy-3-methylglutaryl-coenzyme A reductase---(A;T)T AlleleEffect Directly StudiedPatients with this genotype have a lesser reduction in LDL cholesterol with rosuvastatin.Details
ATP-binding cassette sub-family G member 2---(A;A) / (A;C)G > TEffect Directly StudiedPatients with this genotype have a greater reduction in LDL cholesterol with rosuvastatin.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Rosuvastatin.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Rosuvastatin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Rosuvastatin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Rosuvastatin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Rosuvastatin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Rosuvastatin.
6-Deoxyerythronolide BThe metabolism of Rosuvastatin can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Rosuvastatin.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Rosuvastatin.
AbataceptThe metabolism of Rosuvastatin can be increased when combined with Abatacept.
Food Interactions
Not Available

References

Synthesis Reference

Valerie Niddam-Hildesheim, Greta Sterimbaum, "Process for preparation of rosuvastatin calcium." U.S. Patent US20050080134, issued April 14, 2005.

US20050080134
General References
  1. Di Napoli P, Taccardi AA, Grilli A, De Lutiis MA, Barsotti A, Felaco M, De Caterina R: Chronic treatment with rosuvastatin modulates nitric oxide synthase expression and reduces ischemia-reperfusion injury in rat hearts. Cardiovasc Res. 2005 Jun 1;66(3):462-71. Epub 2005 Mar 2. [PubMed:15914111]
  2. Everett BM, Glynn RJ, MacFadyen JG, Ridker PM: 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). Circulation. 2010 Jan 5;121(1):143-50. doi: 10.1161/CIRCULATIONAHA.109.874834. Epub 2009 Dec 21. [PubMed:20026779]
  3. Jones SP, Gibson MF, Rimmer DM 3rd, Gibson TM, Sharp BR, Lefer DJ: Direct vascular and cardioprotective effects of rosuvastatin, a new HMG-CoA reductase inhibitor. J Am Coll Cardiol. 2002 Sep 18;40(6):1172-8. [PubMed:12354446]
  4. Jones PH, Davidson MH, Stein EA, Bays HE, McKenney JM, Miller E, Cain VA, Blasetto JW: Comparison of the efficacy and safety of rosuvastatin versus atorvastatin, simvastatin, and pravastatin across doses (STELLAR* Trial). Am J Cardiol. 2003 Jul 15;92(2):152-60. [PubMed:12860216]
  5. Kilic E, Kilic U, Matter CM, Luscher TF, Bassetti CL, Hermann DM: 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. Stroke. 2005 Feb;36(2):332-6. Epub 2004 Dec 29. [PubMed:15625301]
  6. Kosmidou I, Moore JP, Weber M, Searles CD: Statin treatment and 3' polyadenylation of eNOS mRNA. Arterioscler Thromb Vasc Biol. 2007 Dec;27(12):2642-9. Epub 2007 Oct 4. [PubMed:17916773]
  7. Laufs U, Gertz K, Dirnagl U, Bohm M, Nickenig G, Endres M: Rosuvastatin, a new HMG-CoA reductase inhibitor, upregulates endothelial nitric oxide synthase and protects from ischemic stroke in mice. Brain Res. 2002 Jun 28;942(1-2):23-30. [PubMed:12031849]
  8. McKillop T: The statin wars. Lancet. 2003 Nov 1;362(9394):1498. [PubMed:14602449]
  9. McTaggart F, Buckett L, Davidson R, Holdgate G, McCormick A, Schneck D, Smith G, Warwick M: Preclinical and clinical pharmacology of Rosuvastatin, a new 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor. Am J Cardiol. 2001 Mar 8;87(5A):28B-32B. [PubMed:11256847]
  10. Nissen SE, Nicholls SJ, Sipahi I, Libby P, Raichlen JS, Ballantyne CM, Davignon J, Erbel R, Fruchart JC, Tardif JC, Schoenhagen P, Crowe T, Cain V, Wolski K, Goormastic M, Tuzcu EM: Effect of very high-intensity statin therapy on regression of coronary atherosclerosis: the ASTEROID trial. JAMA. 2006 Apr 5;295(13):1556-65. Epub 2006 Mar 13. [PubMed:16533939]
  11. Stalker TJ, Lefer AM, Scalia R: A new HMG-CoA reductase inhibitor, rosuvastatin, exerts anti-inflammatory effects on the microvascular endothelium: the role of mevalonic acid. Br J Pharmacol. 2001 Jun;133(3):406-12. [PubMed:11375257]
  12. Authors unspecified: The statin wars: why AstraZeneca must retreat. Lancet. 2003 Oct 25;362(9393):1341. [PubMed:14585629]
  13. Ho RH, Tirona RG, Leake BF, Glaeser H, Lee W, Lemke CJ, Wang Y, Kim RB: Drug and bile acid transporters in rosuvastatin hepatic uptake: function, expression, and pharmacogenetics. Gastroenterology. 2006 May;130(6):1793-806. Epub 2006 Mar 6. [PubMed:16697742]
External Links
Human Metabolome Database
HMDB0015230
KEGG Drug
D08492
PubChem Compound
446157
PubChem Substance
46509022
ChemSpider
393589
BindingDB
18372
ChEBI
38545
ChEMBL
CHEMBL1496
Therapeutic Targets Database
DAP000555
PharmGKB
PA134308647
HET
FBI
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Rosuvastatin
ATC Codes
C10BX10 — Rosuvastatin and valsartanC10BX05 — Rosuvastatin and acetylsalicylic acidC10AA07 — RosuvastatinC10BA06 — Rosuvastatin and ezetimibeG01AE10 — Combinations of sulfonamidesC10BX09 — Rosuvastatin and amlodipineC10BX07 — Rosuvastatin, amlodipine and lisinopril
AHFS Codes
  • 24:06.08 — Hmg-coa Reductase Inhibitors
FDA label
Download (270 KB)
MSDS
Download (57.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceAtherosclerosis / Inflammatory Activity in Carotid Arteries1
0CompletedBasic ScienceAtherosclerosis / Inflammatory Activity in Coronary Arteries1
0CompletedTreatmentFriedreich's Ataxia1
0CompletedTreatmentHIV Seropositivity1
0Unknown StatusPreventionPatients With Coronary Artery Disease Scheduled for by Pass Surgery1
1Active Not RecruitingNot AvailableHealthy Volunteers1
1Active Not RecruitingBasic ScienceNash1
1Active Not RecruitingTreatmentNeoplasms1
1Active Not RecruitingTreatmentProstatic Neoplasms, Castration-Resistant1
1CompletedNot AvailableAcute Coronary Syndromes (ACS)1
1CompletedNot AvailableDrug Drug Interaction (DDI) / Healthy Volunteers / Pharmacokinetics1
1CompletedNot AvailableHealthy Volunteers5
1CompletedNot AvailableHealthy Volunteers / Pharmacokinetics of ASP015K1
1CompletedNot AvailableHepatitis C Viral Infection1
1CompletedNot AvailableHigh Blood Pressure (Hypertension)3
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedNot AvailableImmunosuppression For Disease1
1CompletedBasic ScienceCYP2C19 Poor / Extensive Metabolizers1
1CompletedBasic ScienceDrug Drug Interaction (DDI)1
1CompletedBasic ScienceDrug Drug Interaction (DDI) / Healthy Volunteers / Intestinal Absorption / Pharmacokinetics of Fidaxomicin / Pharmacokinetics of Rosuvastatin1
1CompletedBasic ScienceDrug Interaction Potentiation1
1CompletedBasic ScienceDrug Pharmacokinetics in Healthy Volunteers1
1CompletedBasic ScienceHealthy Participants1
1CompletedBasic ScienceHealthy Volunteers4
1CompletedBasic SciencePharmacokinetic Variables1
1CompletedBasic ScienceRheumatoid Arthritis1
1CompletedOtherHealthy Volunteers3
1CompletedOtherHigh Blood Pressure (Hypertension)1
1CompletedOtherHigh Cholesterol1
1CompletedOtherHigh Risk Coronary Artery Disease1
1CompletedOtherHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1CompletedOtherType 2 Diabetes Mellitus1
1CompletedScreeningDyslipidemias1
1CompletedSupportive CareHealthy Male Volunteers1
1CompletedTreatmentAcute Coronary Syndromes (ACS) / Angioplasty, Transluminal, Percutaneous Coronary / Blood Platelets / Hydroxymethylglutaryl-CoA Reductase Inhibitors1
1CompletedTreatmentAdverse Events / Pharmacokinetic Variables1
1CompletedTreatmentAdverse Events / Pharmacokinetics1
1CompletedTreatmentAnemias1
1CompletedTreatmentAsthma Bronchial1
1CompletedTreatmentAtherosclerosis1
1CompletedTreatmentAtherosclerosis / High Cholesterol1
1CompletedTreatmentCrohn's Disease (CD)1
1CompletedTreatmentDiabetes Mellitus (DM)3
1CompletedTreatmentDiabetes Mellitus (DM) / Healthy Volunteers1
1CompletedTreatmentDiabetes Mellitus (DM) / Hyperlipidemias1
1CompletedTreatmentDyslipidemia, Renal Insufficiency1
1CompletedTreatmentDyslipidemias1
1CompletedTreatmentElderly1
1CompletedTreatmentHealthy Volunteers23
1CompletedTreatmentHepatitis C Virus (HCV) Infection1
1CompletedTreatmentHereditary Angioedema1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1CompletedTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias6
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHypertension and Dyslipidemia1
1CompletedTreatmentHypertriglyceridemias1
1CompletedTreatmentImpaired Renal Function1
1CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
1CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC) / Squamous Cell Carcinoma (SCC)1
1CompletedTreatmentMetabolic Diseases1
1CompletedTreatmentSkin Diseases, Bacterial1
1CompletedTreatmentSystemic Lupus Erythematosus (SLE)1
1CompletedTreatmentCMET-dysregulated Advanced Solid Tumors1
1Enrolling by InvitationNot AvailableHealthy Volunteers1
1Enrolling by InvitationTreatmentHealthy Volunteers1
1Not Yet RecruitingBasic ScienceHealthy Volunteers1
1Not Yet RecruitingTreatmentHealthy Male Volunteers1
1Not Yet RecruitingTreatmentHealthy Volunteers1
1Not Yet RecruitingTreatmentHeathy Volunteer1
1RecruitingBasic ScienceAutoimmune Diseases / Inflammatory Diseases1
1RecruitingBasic ScienceStatin Pharmacokinetics Pre and Post Gastric Bypass Surgery1
1RecruitingTreatmentCancer, Breast1
1RecruitingTreatmentDiabetes Mellitus (DM) / Hyperlipidemias1
1RecruitingTreatmentDyslipidemias1
1RecruitingTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias1
1TerminatedTreatmentCardiovascular Complications / Recurrent Breast Cancer / Stage I Breast Carcinoma / Stage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
1TerminatedTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias1
1TerminatedTreatmentPlasmodium Infections1
1Unknown StatusTreatmentHealthy Volunteers1
1, 2CompletedTreatmentCraniocerebral Injuries1
1, 2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2Unknown StatusTreatmentPre-Eclampsia, Severe1
2Active Not RecruitingSupportive CareCancer, Breast1
2CompletedPreventionDeep Vein Thrombosis (DVT) / Neoplasms / Venous Thromboembolism (VTE)1
2CompletedPreventionHeart Diseases / Human Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHigh Cholesterol1
2CompletedPreventionMinor burns1
2CompletedTreatmentAtherosclerosis / Systemic Lupus Erythematosus (SLE)1
2CompletedTreatmentCardiovascular Disease (CVD) / Endothelial Dysfunction1
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2CompletedTreatmentCoronary Artery Disease / Obstructive Coronary Artery Disease1
2CompletedTreatmentCraniocerebral Injuries1
2CompletedTreatmentDiabetes Mellitus (DM)1
2CompletedTreatmentDiabetic Polyneuropathy1
2CompletedTreatmentDiabetic Polyneuropathy / Oxidative Stress1
2CompletedTreatmentDyslipidemias2
2CompletedTreatmentHeart Failure, Unspecified1
2CompletedTreatmentHepatitis C Viral Infection1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Hyperlipidemias1
2CompletedTreatmentHyperlipidemias1
2CompletedTreatmentIntracerebral Hemorrhage / Strokes1
2CompletedTreatmentPlatelets Dysfunction1
2CompletedTreatmentRheumatoid Arthritis1
2CompletedTreatmentTransient ischemia attacks1
2Not Yet RecruitingTreatmentCoronary Heart Disease (CHD) / Human Immunodeficiency Virus (HIV) Infections1
2Not Yet RecruitingTreatmentCoronary Syndrome1
2Not Yet RecruitingTreatmentDyslipidemias1
2RecruitingPreventionCancer of the Ovary1
2RecruitingPreventionVenous Thromboembolism (VTE)1
2RecruitingTreatmentArteriovenous Fistulas / Diabetes Mellitus (DM) / End-Stage Kidney Disease1
2RecruitingTreatmentMetabolic Syndromes / Osteoporosis / Osteoporosis and Cardio-Metabolic Syndrome Following Spinal Cord Injury / Spinal Cord Injuries (SCI)1
2RecruitingTreatmentRectal Carcinoma1
2RecruitingTreatmentVenous Thromboembolism (VTE) / Wounds and Injuries1
2TerminatedBasic ScienceCoronary Artery Disease / Dyslipidemias1
2TerminatedTreatmentCritically-ill Patients / H1N1/Influenza Infection1
2TerminatedTreatmentInfluenza A Virus Infection1
2Unknown StatusNot AvailableInfection, Human Immunodeficiency Virus I1
2Unknown StatusTreatmentAcute Myocardial Infarction (AMI)1
2Unknown StatusTreatmentDepression1
2Unknown StatusTreatmentSepsis1
2, 3CompletedTreatmentBlood Pressures / Glomerular Filtration Rate (GFR) / Lipids / Renal Artery Obstruction / Stents1
2, 3CompletedTreatmentPeriodontitis, Chronic3
2, 3CompletedTreatmentRheumatoid Arthritis1
2, 3RecruitingTreatmentGastroesophageal variceal hemorrhage prophylaxis / Liver Cirrhosis / Portal Hypertension1
2, 3RecruitingTreatmentHyperlipidemias1
2, 3TerminatedTreatmentCardiovascular Disease (CVD) / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingPreventionANCA-associated Primary Necrotizing Vasculitides1
3Active Not RecruitingTreatmentAtherosclerosis1
3CompletedNot AvailableHigh Cholesterol1
3CompletedPreventionAtherosclerotic Disease / Postoperative Hemorrhages1
3CompletedPreventionHeart Failure, Unspecified1
3CompletedPreventionRenal Failure1
3CompletedTreatmentAcute Coronary Syndromes (ACS)2
3CompletedTreatmentAortic Valve Stenosis1
3CompletedTreatmentAssess the Periprocedural Myocardial Necrosis1
3CompletedTreatmentAtherosclerosis2
3CompletedTreatmentAtherosclerosis / Cardiovascular Disease (CVD)1
3CompletedTreatmentAtherosclerosis / Coronary Heart Disease (CHD) / High Cholesterol2
3CompletedTreatmentCardiovascular Disorders / Diabetes Mellitus (DM)1
3CompletedTreatmentCarotid Artery Stenosis / High Cholesterol1
3CompletedTreatmentCholesterolemia / High Blood Pressure (Hypertension)1
3CompletedTreatmentCongestive Cardiomyopathy1
3CompletedTreatmentCongestive Heart Failure (CHF)1
3CompletedTreatmentCoronary Arteriosclerosis1
3CompletedTreatmentCoronary Artery Atherosclerosis1
3CompletedTreatmentCoronary Artery Disease / Myocardial Ischemia1
3CompletedTreatmentCoronary Heart Disease (CHD) / Dyslipidemias / Mixed hypercholesterolemia2
3CompletedTreatmentCoronary Heart Disease (CHD) / High Cholesterol1
3CompletedTreatmentDiabetic Dyslipidemia / Type 2 Diabetes Mellitus1
3CompletedTreatmentDyslipidemia (Fredrickson Type Ⅱa)3
3CompletedTreatmentDyslipidemia (Fredrickson Type Ⅱa) / High Cholesterol1
3CompletedTreatmentDyslipidemia With Hypertension1
3CompletedTreatmentDyslipidemias1
3CompletedTreatmentDyslipidemias / High Blood Pressure (Hypertension)2
3CompletedTreatmentDyslipidemias / High Cholesterol4
3CompletedTreatmentDyslipidemias / Kidney Diseases1
3CompletedTreatmentDyslipidemias / Metabolic Syndromes2
3CompletedTreatmentDyslipidemias / Type 2 Diabetes Mellitus2
3CompletedTreatmentEssential Hypertension, Dyslipidemia1
3CompletedTreatmentFredrickson Type IIa & Type IIb Dyslipidaemia1
3CompletedTreatmentHeart Failure, Unspecified1
3CompletedTreatmentHeart Failure, Unspecified / Positron Emission Tomography (PET) / Rosuvastatin1
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias2
3CompletedTreatmentHigh Cholesterol23
3CompletedTreatmentHomozygous Familial Hypercholesterolemia (HoFH)2
3CompletedTreatmentHyperlipidemias1
3CompletedTreatmentHyperlipoproteinemia Type III1
3CompletedTreatmentHypertension With Hyperlipidemia1
3CompletedTreatmentMetabolic Syndromes1
3CompletedTreatmentObesity, Abdominal1
3CompletedTreatmentPeriprocedural Myocardial Necrosis1
3CompletedTreatmentSclerosis, Progressive Systemic1
3CompletedTreatmentType 2 Diabetes Mellitus1
3CompletedTreatmentMixed hypercholesterolemia2
3Not Yet RecruitingTreatmentDyslipidemias1
3Not Yet RecruitingTreatmentDyslipidemias / Hypertriglyceridemias1
3Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3RecruitingPreventionCardiovascular Disease (CVD) / Coronary Artery Disease / Type 2 Diabetes Mellitus1
3RecruitingTreatmentCoronary Artery Disease1
3RecruitingTreatmentDyslipidemias / Hypertension,Essential1
3RecruitingTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias2
3RecruitingTreatmentHigh Cholesterol2
3TerminatedPreventionElevated High-sensitivity C-Reactive Protein (hsCRP)1
3TerminatedTreatmentAcute Lung Injury (ALI) / Sepsis1
3TerminatedTreatmentColorectal Cancers / Precancerous Conditions1
3TerminatedTreatmentHigh Cholesterol3
3TerminatedTreatmentHip Fractures1
3TerminatedTreatmentStable Coronary Artery Disease Undergoing PCI1
3TerminatedTreatmentStrokes1
3Unknown StatusPreventionCoronary Heart Disease (CHD)1
3Unknown StatusTreatmentCoronary Artery Disease1
3Unknown StatusTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias1
3Unknown StatusTreatmentHigh Cholesterol1
3Unknown StatusTreatmentValvular Cardiac Surgery1
3WithdrawnTreatmentPulmonary Embolism (PE) / Thrombosis, Venous1
4Active Not RecruitingTreatment22q Telomere Deletion Syndrome / Telomere Length, Mean Leukocyte / Telomere Shortening1
4Active Not RecruitingTreatmentDyslipidemias1
4Active Not RecruitingTreatmentHyperlipidemias / Sexual Dysfunctions1
4CompletedNot AvailableAtherosclerosis / High Cholesterol1
4CompletedNot AvailableCoronary Heart Disease (CHD)1
4CompletedNot AvailableSexual Dysfunctions1
4CompletedBasic ScienceHigh Cholesterol / Type 2 Diabetes Mellitus1
4CompletedDiagnosticCardiovascular Disease (CVD) / Human Immunodeficiency Virus (HIV)1
4CompletedHealth Services ResearchDiabetes Mellitus (DM) / Dyslipidemias1
4CompletedPreventionAcute Coronary Syndromes (ACS)2
4CompletedPreventionAdverse Effects / Coronary Artery Atherosclerosis / Insulin resistance syndrome1
4CompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD)1
4CompletedPreventionAtherosclerosis / Systemic Lupus Erythematosus (SLE) / Thromboembolism1
4CompletedPreventionCardiovascular Disease (CVD) / Strokes1
4CompletedPreventionChronic Kidney Disease (CKD) / Diabetes Mellitus (DM)1
4CompletedPreventionEndothelial Dysfunction / Ischemia Reperfusion Injury1
4CompletedPreventionIschemia Reperfusion Injury1
4CompletedPreventionMyocardium; Injury / Nonvalvular Atrial Fibrillation1
4CompletedPreventionRenal Dysfunction1
4CompletedSupportive CareA Total of 234 Patients With Acute Coronary Syndrome Who Will Undergo OPCAB1
4CompletedTreatmentAcute Coronary Syndromes (ACS) / Dyslipidemias1
4CompletedTreatmentAcute Coronary Syndromes (ACS) / High Cholesterol1
4CompletedTreatmentAdult Periodontitis1
4CompletedTreatmentAngina Pectoris1
4CompletedTreatmentAtherosclerosis / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / Dyslipidemias / Strokes1
4CompletedTreatmentAtherosclerosis / Endothelial Dysfunction1
4CompletedTreatmentCardiovascular Risk Factors / High Blood Pressure (Hypertension)1
4CompletedTreatmentCoronary Artery Disease2
4CompletedTreatmentCoronary Artery Disease Progression1
4CompletedTreatmentCoronary Artery Disease / Hyperlipidemias1
4CompletedTreatmentDiabetes Mellitus (DM)2
4CompletedTreatmentDisorder Related to Renal Transplantation / High Cholesterol1
4CompletedTreatmentDyslipidemia (Fredrickson Type Ⅱa)1
4CompletedTreatmentFurcation Defects1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHigh Cholesterol5
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Hyperlipidemias1
4CompletedTreatmentHyperlipidemias1
4CompletedTreatmentHyperlipidemias / Hyperlipoproteinemia Type IIb / Hyperlipoproteinemia Type iv / Hyperlipoproteinemia Type V / Hypertriglyceridemias1
4CompletedTreatmentHypertriglycemia / Type 2 Diabetes Mellitus1
4CompletedTreatmentMetabolic Syndromes2
4CompletedTreatmentMyocardial Infarction [C14.907.585.500]1
4CompletedTreatmentOrganic Anion Transporting Polypeptide1B1 (OATP1B1) / Rosuvastatin1
4CompletedTreatmentST Segment Elevation Myocardial Infarction (STEMI) / Subclinical Carotid Atherosclerosis1
4CompletedTreatmentSleep Apnea, Obstructive1
4CompletedTreatmentStroke, Ischemic1
4CompletedTreatmentType 2 Diabetes Mellitus1
4CompletedTreatmentType IIa and IIb Hypercholesterolaemia1
4Enrolling by InvitationTreatmentCerebral Infarctions / CLOPIDOGREL, POOR METABOLISM of (Disorder)1
4Enrolling by InvitationTreatmentChronic Total Occlusion of Coronary Artery / Coronary Artery Disease / Percutaneous Coronary Intervention / Viable Myocardium1
4Enrolling by InvitationTreatmentComplete Occlusion of Coronary Artery / Hibernation, Myocardial1
4Not Yet RecruitingPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Molecular Imaging1
4Not Yet RecruitingPreventionCoronary Artery Disease1
4Not Yet RecruitingTreatmentAngina Pectoris / Coronary Artery Disease1
4Not Yet RecruitingTreatmentArterial Hypertension1
4Not Yet RecruitingTreatmentChronic Kidney Disease (CKD) / Proteinuria1
4Not Yet RecruitingTreatmentDyslipidemias / Nonalcoholic Fatty Liver Disease1
4Not Yet RecruitingTreatmentInfarction, Anterior Cerebral Artery1
4Not Yet RecruitingTreatmentIntracranial Arterial Stenosis1
4Not Yet RecruitingTreatmentIschemic1
4Not Yet RecruitingTreatmentParoxysmal Atrial Fibrillation (PAF)1
4RecruitingHealth Services ResearchDiabetes Mellitus (DM)1
4RecruitingPreventionHigh Blood Pressure (Hypertension) / Strokes / Transient Ischaemic Attack (TIA)1
4RecruitingTreatmentAcute Coronary Syndromes (ACS)1
4RecruitingTreatmentAtherosclerosis1
4RecruitingTreatmentCardiovascular Disease (CVD)1
4RecruitingTreatmentCardiovascular Disease (CVD) / Coronary Artery Disease / Coronary Heart Disease (CHD)1
4RecruitingTreatmentCarotid Atherosclerosis1
4RecruitingTreatmentCoronary Artery Disease1
4RecruitingTreatmentCoronary Artery Dissection, Spontaneous1
4RecruitingTreatmentDiabetes Mellitus and Hypercholesterolemia1
4RecruitingTreatmentHigh Blood Pressure (Hypertension)1
4RecruitingTreatmentHigh Cholesterol1
4RecruitingTreatmentMetabolic Syndromes1
4RecruitingTreatmentMyocardial Fibrosis1
4RecruitingTreatmentST Elevation Myocardial Infarction (STEMI)1
4TerminatedNot AvailableDyslipidemias1
4TerminatedNot AvailableStatin Adverse Reaction / Statin-Associated Myopathy1
4TerminatedTreatmentAtherosclerosis1
4TerminatedTreatmentAtherosclerosis / Coronary Artery Disease / High Cholesterol1
4TerminatedTreatmentAtherosclerosis / Human Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentCoronary Arteriosclerosis1
4TerminatedTreatmentHigh Cholesterol1
4TerminatedTreatmentStrokes / Transient Ischaemic Attack (TIA)1
4Unknown StatusPreventionCardiovascular Disease (CVD) / Human Immunodeficiency Virus (HIV)1
4Unknown StatusTreatmentAcute Coronary Syndromes (ACS)1
4Unknown StatusTreatmentAtherosclerosis / Hyperlipidemias1
4Unknown StatusTreatmentCoronary Artery Disease4
4Unknown StatusTreatmentCoronary Artery Disease / Hyperlipidemias1
4Unknown StatusTreatmentCoronary Heart Disease (CHD) / High Cholesterol1
4Unknown StatusTreatmentDyslipidemias1
4Unknown StatusTreatmentFocus of Study1
4Unknown StatusTreatmentHigh Cholesterol1
4Unknown StatusTreatmentHigh LDL Cholesterol Level / Systemic Lupus Erythematosus (SLE)1
4Unknown StatusTreatmentNon-ST-elevation Acute Coronary Syndromes1
4Unknown StatusTreatmentNon-familial hypercholesterolemia / Physical Inactivity1
4WithdrawnBasic ScienceDiabetes Mellitus (DM) / Glaucoma1
4WithdrawnTreatmentDyslipidemia (Fredrickson Type Ⅱa)1
Not AvailableCompletedNot AvailableAnkylosing Spondylitis (AS) / Carotid Artery Plaque / Rheumatoid Arthritis1
Not AvailableCompletedNot AvailableCardiovascular Disease (CVD) / Type 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableCerebrovascular Accidents / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / High Cholesterol / Peripheral Vascular Disease (PVD)1
Not AvailableCompletedNot AvailableDyslipidemia (Fredrickson Type Ⅱa)1
Not AvailableCompletedNot AvailableHigh Cholesterol2
Not AvailableCompletedBasic ScienceAdenosine Metabolism1
Not AvailableCompletedBasic ScienceDeep Vein Thrombosis (DVT) / Pulmonary Embolism (PE)1
Not AvailableCompletedTreatmentAcute Coronary Syndromes (ACS)1
Not AvailableCompletedTreatmentHigh Cholesterol / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHypercholesterolemia With Concomitant Type 2 Diabetes1
Not AvailableNot Yet RecruitingNot AvailableAcute Ischemic Stroke AIS / Intracranial Atherosclerosis ICAS1
Not AvailableRecruitingBasic ScienceAtherosclerosis / Cardiovascular Disease (CVD)1
Not AvailableRecruitingPreventionAcute Coronary Syndromes (ACS)1
Not AvailableRecruitingTreatmentArteriosclerosis / Diabetes Mellitus (DM) / Lipid Disorders1
Not AvailableRecruitingTreatmentCardiovascular Disease (CVD) / Cerebrovascular Diseases / Peripheral Atherosclerotic Disease1
Not AvailableRecruitingTreatmentCoronary Artery Occlusive Disease1
Not AvailableRecruitingTreatmentIntracranial Arterial Diseases1
Not AvailableTerminatedPreventionHigh Blood Pressure (Hypertension) / High Cholesterol / Type 2 Diabetes Mellitus1
Not AvailableTerminatedTreatmentAcute Respiratory Distress Syndrome (ARDS) / Flu caused by Influenza / Influenza A Virus Infection1
Not AvailableUnknown StatusTreatmentAcute Coronary Syndromes (ACS) / Diabetes Mellitus (DM)1
Not AvailableUnknown StatusTreatmentAcute Respiratory Distress Syndrome (ARDS) / Blunt Chest Trauma1
Not AvailableUnknown StatusTreatmentHigh Cholesterol1
Not AvailableWithdrawnNot AvailablePCI Patients1
Not AvailableWithdrawnTreatmentHepatitis C Viral Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • A-S Medication Solutions LLC
  • AstraZeneca Inc.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Corden Pharma GmbH
  • IPR Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Southwood Pharmaceuticals
Dosage forms
FormRouteStrength
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral40 mg/1
Tablet, film coatedOral5 mg/1
TabletOral10 mg
TabletOral20 mg
TabletOral40 mg
TabletOral5 mg
TabletOral10.0 mg
TabletOral20.0 mg
TabletOral40.0 mg
TabletOral5.0 mg
TabletOral10 mg/1
TabletOral20 mg/1
TabletOral40 mg/1
TabletOral5 mg/1
Tablet, coatedOral10 mg/1
Tablet, coatedOral20 mg/1
Tablet, coatedOral40 mg/1
Tablet, coatedOral5 mg/1
Prices
Unit descriptionCostUnit
Crestor 40 mg tablet4.7USD tablet
Crestor 20 mg tablet4.69USD tablet
Crestor 10 mg tablet4.68USD tablet
Crestor 5 mg tablet4.68USD tablet
Crestor 40 mg Tablet2.24USD tablet
Crestor 20 mg Tablet1.91USD tablet
Crestor 10 mg Tablet1.53USD tablet
Crestor 5 mg Tablet1.45USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2315141No2009-08-182020-08-04Canada
CA2072945No2001-07-312012-07-02Canada
US6858618Yes2005-02-222022-06-17Us
US7030152Yes2006-04-182018-10-02Us
US7964614Yes2011-06-212018-10-02Us
US6316460Yes2001-11-132021-02-04Us
USRE37314Yes2001-08-072016-07-08Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySparingly soluble in waterFDA label
logP0.13 FDA label
Predicted Properties
PropertyValueSource
Water Solubility0.0886 mg/mLALOGPS
logP1.47ALOGPS
logP1.92ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area140.92 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity121.44 m3·mol-1ChemAxon
Polarizability48.55 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9791
Blood Brain Barrier-0.6815
Caco-2 permeable-0.5818
P-glycoprotein substrateNon-substrate0.6962
P-glycoprotein inhibitor INon-inhibitor0.5099
P-glycoprotein inhibitor IINon-inhibitor0.8987
Renal organic cation transporterNon-inhibitor0.9467
CYP450 2C9 substrateNon-substrate0.5544
CYP450 2D6 substrateNon-substrate0.8633
CYP450 3A4 substrateNon-substrate0.584
CYP450 1A2 substrateNon-inhibitor0.6896
CYP450 2C9 inhibitorNon-inhibitor0.5957
CYP450 2D6 inhibitorNon-inhibitor0.8609
CYP450 2C19 inhibitorNon-inhibitor0.6414
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6226
Ames testNon AMES toxic0.662
CarcinogenicityNon-carcinogens0.6578
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5599 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9856
hERG inhibition (predictor II)Non-inhibitor0.8117
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpyrimidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrimidine ring through a CC or CN bond. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Phenylpyrimidines
Alternative Parents
Medium-chain hydroxy acids and derivatives / Medium-chain fatty acids / Beta hydroxy acids and derivatives / Fluorobenzenes / Halogenated fatty acids / Heterocyclic fatty acids / Hydroxy fatty acids / Aryl fluorides / Unsaturated fatty acids / Organosulfonamides
show 13 more
Substituents
4-phenylpyrimidine / 5-phenylpyrimidine / Medium-chain hydroxy acid / Medium-chain fatty acid / Beta-hydroxy acid / Fluorobenzene / Halobenzene / Halogenated fatty acid / Heterocyclic fatty acid / Hydroxy fatty acid
show 33 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
statin (synthetic), sulfonamide, pyrimidines, dihydroxy monocarboxylic acid, monofluorobenzenes (CHEBI:38545)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Nadph binding
Specific Function
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including...
Gene Name
HMGCR
Uniprot ID
P04035
Uniprot Name
3-hydroxy-3-methylglutaryl-coenzyme A reductase
Molecular Weight
97475.155 Da
References
  1. Carbonell T, Freire E: Binding thermodynamics of statins to HMG-CoA reductase. Biochemistry. 2005 Sep 6;44(35):11741-8. [PubMed:16128575]
  2. Chapman MJ, Caslake M, Packard C, McTaggart F: New dimension of statin action on ApoB atherogenicity. Clin Cardiol. 2003 Jan;26(1 Suppl 1):I7-10. [PubMed:12539816]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  4. Davidson MH: Rosuvastatin: a highly efficacious statin for the treatment of dyslipidaemia. Expert Opin Investig Drugs. 2002 Jan;11(1):125-41. [PubMed:11772327]
  5. Hanefeld M: Clinical rationale for rosuvastatin, a potent new HMG-CoA reductase inhibitor. Int J Clin Pract. 2001 Jul-Aug;55(6):399-405. [PubMed:11501230]
  6. Holdgate GA, Ward WH, McTaggart F: Molecular mechanism for inhibition of 3-hydroxy-3-methylglutaryl CoA (HMG-CoA) reductase by rosuvastatin. Biochem Soc Trans. 2003 Jun;31(Pt 3):528-31. [PubMed:12773150]
  7. McTaggart F, Buckett L, Davidson R, Holdgate G, McCormick A, Schneck D, Smith G, Warwick M: Preclinical and clinical pharmacology of Rosuvastatin, a new 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor. Am J Cardiol. 2001 Mar 8;87(5A):28B-32B. [PubMed:11256847]
  8. Olsson AG, McTaggart F, Raza A: Rosuvastatin: a highly effective new HMG-CoA reductase inhibitor. Cardiovasc Drug Rev. 2002 Winter;20(4):303-28. [PubMed:12481202]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Sakaeda T, Fujino H, Komoto C, Kakumoto M, Jin JS, Iwaki K, Nishiguchi K, Nakamura T, Okamura N, Okumura K: Effects of acid and lactone forms of eight HMG-CoA reductase inhibitors on CYP-mediated metabolism and MDR1-mediated transport. Pharm Res. 2006 Mar;23(3):506-12. doi: 10.1007/s11095-005-9371-5. Epub 2006 Jan 1. [PubMed:16388406]
  2. Rosuvastatin FDA [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Sakaeda T, Fujino H, Komoto C, Kakumoto M, Jin JS, Iwaki K, Nishiguchi K, Nakamura T, Okamura N, Okumura K: Effects of acid and lactone forms of eight HMG-CoA reductase inhibitors on CYP-mediated metabolism and MDR1-mediated transport. Pharm Res. 2006 Mar;23(3):506-12. doi: 10.1007/s11095-005-9371-5. Epub 2006 Jan 1. [PubMed:16388406]
  3. Davidson MH: Rosuvastatin: a highly efficacious statin for the treatment of dyslipidaemia. Expert Opin Investig Drugs. 2002 Mar;11(3):125-41. [PubMed:12769127]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Sakaeda T, Fujino H, Komoto C, Kakumoto M, Jin JS, Iwaki K, Nishiguchi K, Nakamura T, Okamura N, Okumura K: Effects of acid and lactone forms of eight HMG-CoA reductase inhibitors on CYP-mediated metabolism and MDR1-mediated transport. Pharm Res. 2006 Mar;23(3):506-12. doi: 10.1007/s11095-005-9371-5. Epub 2006 Jan 1. [PubMed:16388406]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Knauer MJ, Urquhart BL, Meyer zu Schwabedissen HE, Schwarz UI, Lemke CJ, Leake BF, Kim RB, Tirona RG: Human skeletal muscle drug transporters determine local exposure and toxicity of statins. Circ Res. 2010 Feb 5;106(2):297-306. doi: 10.1161/CIRCRESAHA.109.203596. Epub 2009 Nov 25. [PubMed:19940267]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Knauer MJ, Urquhart BL, Meyer zu Schwabedissen HE, Schwarz UI, Lemke CJ, Leake BF, Kim RB, Tirona RG: Human skeletal muscle drug transporters determine local exposure and toxicity of statins. Circ Res. 2010 Feb 5;106(2):297-306. doi: 10.1161/CIRCRESAHA.109.203596. Epub 2009 Nov 25. [PubMed:19940267]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Ho RH, Tirona RG, Leake BF, Glaeser H, Lee W, Lemke CJ, Wang Y, Kim RB: Drug and bile acid transporters in rosuvastatin hepatic uptake: function, expression, and pharmacogenetics. Gastroenterology. 2006 May;130(6):1793-806. Epub 2006 Mar 6. [PubMed:16697742]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. van de Steeg E, Greupink R, Schreurs M, Nooijen IH, Verhoeckx KC, Hanemaaijer R, Ripken D, Monshouwer M, Vlaming ML, DeGroot J, Verwei M, Russel FG, Huisman MT, Wortelboer HM: Drug-drug interactions between rosuvastatin and oral antidiabetic drugs occurring at the level of OATP1B1. Drug Metab Dispos. 2013 Mar;41(3):592-601. doi: 10.1124/dmd.112.049023. Epub 2012 Dec 17. [PubMed:23248200]
  2. Karlgren M, Ahlin G, Bergstrom CA, Svensson R, Palm J, Artursson P: In vitro and in silico strategies to identify OATP1B1 inhibitors and predict clinical drug-drug interactions. Pharm Res. 2012 Feb;29(2):411-26. doi: 10.1007/s11095-011-0564-9. Epub 2011 Aug 23. [PubMed:21861202]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Ho RH, Tirona RG, Leake BF, Glaeser H, Lee W, Lemke CJ, Wang Y, Kim RB: Drug and bile acid transporters in rosuvastatin hepatic uptake: function, expression, and pharmacogenetics. Gastroenterology. 2006 May;130(6):1793-806. Epub 2006 Mar 6. [PubMed:16697742]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Ho RH, Tirona RG, Leake BF, Glaeser H, Lee W, Lemke CJ, Wang Y, Kim RB: Drug and bile acid transporters in rosuvastatin hepatic uptake: function, expression, and pharmacogenetics. Gastroenterology. 2006 May;130(6):1793-806. Epub 2006 Mar 6. [PubMed:16697742]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cystine:glutamate antiporter activity
Specific Function
Sodium-independent, high-affinity exchange of anionic amino acids with high specificity for anionic form of cystine and glutamate.
Gene Name
SLC7A11
Uniprot ID
Q9UPY5
Uniprot Name
Cystine/glutamate transporter
Molecular Weight
55422.44 Da
References
  1. Ho RH, Tirona RG, Leake BF, Glaeser H, Lee W, Lemke CJ, Wang Y, Kim RB: Drug and bile acid transporters in rosuvastatin hepatic uptake: function, expression, and pharmacogenetics. Gastroenterology. 2006 May;130(6):1793-806. Epub 2006 Mar 6. [PubMed:16697742]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Jemnitz K, Veres Z, Tugyi R, Vereczkey L: Biliary efflux transporters involved in the clearance of rosuvastatin in sandwich culture of primary rat hepatocytes. Toxicol In Vitro. 2010 Mar;24(2):605-10. doi: 10.1016/j.tiv.2009.10.009. Epub 2009 Oct 21. [PubMed:19853032]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Ellis LC, Hawksworth GM, Weaver RJ: ATP-dependent transport of statins by human and rat MRP2/Mrp2. Toxicol Appl Pharmacol. 2013 Jun 1;269(2):187-94. doi: 10.1016/j.taap.2013.03.019. Epub 2013 Apr 2. [PubMed:23562342]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
Substrate activity was demonstrated in vitro using human and rat OAT3 expressed on Xenopus Laevis.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [PubMed:19953504]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 12:39