Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H36O7 |
Molecular Weight | 424.5277 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@H](C)C(=O)O[C@H]1C[C@H](O)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12
InChI
InChIKey=TUZYXOIXSAXUGO-PZAWKZKUSA-N
InChI=1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1
Molecular Formula | C23H36O7 |
Molecular Weight | 424.5277 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Pravastatin (marketed as Pravachol or Selektine) is a member of the drug class of statins, used in combination with diet, exercise, and weight loss for lowering cholesterol and preventing cardiovascular disease. Pravastatin acts as a lipoprotein-lowering drug through two pathways. In the major pathway, pravastatin inhibits the function of hydroxymethylglutaryl-CoA (HMG-CoA) reductase. As a reversible competitive inhibitor, pravastatin sterically hinders the action of HMG-CoA reductase by occupying the active site of the enzyme. Taking place primarily in the liver, this enzyme is responsible for the conversion of HMG-CoA to mevalonate in the rate-limiting step of the biosynthetic pathway for cholesterol. Pravastatin also inhibits the synthesis of very-low-density lipoproteins, which are the precursor to low-density lipoproteins (LDL). These reductions increase the number of cellular LDL receptors, thus LDL uptake increases, removing it from the bloodstream. Pravastatin is primarily used for the treatment of dyslipidemia and the prevention of cardiovascular disease. It is recommended to be used only after other measures, such as diet, exercise, and weight reduction, have not improved cholesterol levels. The evidence for the use of pravastatin is generally weaker than for other statins. The antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT), failed to demonstrate a difference in all-cause mortality or nonfatal myocardial infarction/fatal coronary heart disease rates between patients receiving pravastatin 40 mg daily (a common starting dose) and those receiving usual care. Pravastatin is generally well tolerated; adverse reactions have usually been mild and transient. In 4-month-long placebo-controlled trials, 1.7% of Pravastatin-treated patients and 1.2% of placebo-treated patients were discontinued from treatment because of adverse experiences attributed to study drug therapy; this difference was not statistically significant.
CNS Activity
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Pravastatin attenuates lower torso ischaemia-reperfusion-induced lung injury by upregulating constitutive endothelial nitric oxide synthase. | 2001 Apr |
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Baseline characteristics of the diabetic participants in the Antihypertensive and Lipid-Lowering Treatment to Prevent Heart Attack Trial (ALLHAT). | 2001 Apr |
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Therapeutic change of HMG-CoA reductase inhibitors in patients with coronary artery disease. | 2001 Apr |
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Mevastatin, an HMG-CoA reductase inhibitor, reduces stroke damage and upregulates endothelial nitric oxide synthase in mice. | 2001 Apr |
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Comparative study of HMG-CoA reductase inhibitors on fibrinogen. | 2001 Apr |
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[Effect on plasma fibrinogen of hypercholesterolaemia treatment with pravastatin]. | 2001 Apr 15 |
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Assessing the results: phase 1 hyperlipidemia outcomes in 27 health plans. | 2001 Apr 16 |
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[Acute coronary syndrome. Early lipid reduction decreases risk of recurrence]. | 2001 Apr 19 |
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New pharmacologic aspects of CS-866, the newest angiotensin II receptor antagonist. | 2001 Apr 19 |
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Reassuring effect of pravastatin on natural killer cell activity in stable renal transplant patients. | 2001 Apr 27 |
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Clinical relevance of statins: their role in secondary prevention. | 2001 Feb |
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[Acute coronary syndrome. Statins in the early phase save lives]. | 2001 Feb 8 |
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Stimulation of inflammatory responses in vitro and in vivo by lipophilic HMG-CoA reductase inhibitors. | 2001 Jan |
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Statin therapy and the prevention of dementia. | 2001 Jun |
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Safety and efficacy of pravastatin therapy for the prevention of hyperlipidemia in pediatric and adolescent cardiac transplant recipients. | 2001 Jun |
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Simvastatin-associated memory loss. | 2001 Jun |
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HMG-CoA reductase inhibitors prevent migration of human coronary smooth muscle cells through suppression of increase in oxidative stress. | 2001 Jun |
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Effect of lovastatin, an HMG CoA reductase inhibitor, on acute renal allograft rejection. | 2001 Jun |
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Statins selectively inhibit leukocyte function antigen-1 by binding to a novel regulatory integrin site. | 2001 Jun |
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Fluvastatin suppresses oxidative stress and fibrosis in the interstitium of mouse kidneys with unilateral ureteral obstruction. | 2001 Jun |
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Randomized clinical trials and recent patterns in the use of statins. | 2001 Jun |
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The pravastatin inflammation CRP evaluation (PRINCE): rationale and design. | 2001 Jun |
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PRINCE's prospects: statins, inflammation, and coronary risk. | 2001 Jun |
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Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes. | 2001 Jun |
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Limitation of heart growth in neonatal piglets by simvastatin and atorvastatin: comparison with pravastatin. | 2001 Jun |
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Compactin enhances osteogenesis in murine embryonic stem cells. | 2001 Jun 8 |
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[PATE Study [Pravastatin anti-Atherosclerosis Trial in the Elderly Study]]. | 2001 Mar |
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[CARE[ Cholesterol and Recurrent Events Trial]]. | 2001 Mar |
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[REGRESS [The Regression Growth Evaluation Statin Study]]. | 2001 Mar |
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[LIPID study [Long-term Intervention with Pravastatin in Ischaemic Disease study]]. | 2001 Mar |
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[WOSCOPS [West of Scotland Coronary Prevention Study]]. | 2001 Mar |
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Is a statin a statin? | 2001 Mar |
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Role of fibrates and HMG-CoA reductase inhibitors in gallstone formation: epidemiological study in an unselected population. | 2001 Mar |
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[Effects of pravastatin in 3260 patients with unstable angina: results from the LIPID study]. | 2001 Mar |
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[Treatment with statins for the reduction of cardiovascular risk]. | 2001 Mar |
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Medical-economical aspects of high sensitivity C-reactive protein assay for the prediction of coronary heart disease. An analysis in Germany and Italy. | 2001 Mar |
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Dementia and statins. | 2001 Mar 17 |
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Protective effects of Saiko-ka-ryukotsu-borei-to (Chai-Hu-Jia-Long-Gu-Mu-Li-Tang) against atherosclerosis in Kurosawa and Kusanagi-hypercholesterolemic (KHC) rabbits. | 2001 May |
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Statin induced myopathy does not show up in MIBI scintigraphy. | 2001 May |
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[Pravastatin and the development of diabetes mellitus. Evidence for a protective treatment effect in the West of Scotland Coronary Prevention Study]. | 2001 May |
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What do the statin trials tell us? | 2001 May |
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The in vitro inhibitory effect of tannin derivatives on 3-hydroxy-3-methylglutaryl-coenzyme a reductase on vero cells. | 2001 May |
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Interactions of leptin and thyrotropin 24-hour secretory profiles in short normal children. | 2001 May |
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Effects of 1-year treatment with fluvastatin or pravastatin on bone. | 2001 May |
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Cost-effectiveness of pravastatin therapy for survivors of myocardial infarction with average cholesterol levels. | 2001 May |
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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 |
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[Statins as new therapeutic possibility in osteoporosis?]. | 2001 May 11 |
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Summaries for patients. Benefits of lowering cholesterol levels in older patients. | 2001 May 15 |
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Benefits of pravastatin on cardiovascular events and mortality in older patients with coronary heart disease are equal to or exceed those seen in younger patients: Results from the LIPID trial. | 2001 May 15 |
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Synthesis and biological evaluations of condensed pyridine and condensed pyrimidine-based HMG-CoA reductase inhibitors. | 2001 May 21 |
Sample Use Guides
May be beneficial for prophylaxis of cardiovascular events in at-risk patients, even if patients have normal levels of cholesterol. 10-40 mg PO qDay; not to exceed 80 mg/day Initiate with 10 mg qHS if taking immunosuppressants like cyclosporine concurrently; not to exceed 20 mg/day Limit maximum to 40 mg/day if taking concurrently with clarithromycin Dose adjustments should be made at intervals of 4 weeks or more; individualize dosing according to baseline LDL cholesterol levels
Route of Administration:
Oral
Pravastatin activity was evaluated using cellular steroidgenesis assay in Hep G2cells (human hepatoma cell line) cultured with 5% lipoprotein deficient serum containing medium for 48 h. The activities were determined by decreased incorporation of sodium [2-14C] acetate into non-saponifiable lipids.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Oct 21 20:59:10 UTC 2019
by
admin
on
Mon Oct 21 20:59:10 UTC 2019
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Record UNII |
KXO2KT9N0G
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Record Status |
Validated (UNII)
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Record Version |
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Official Name | English | ||
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WHO-VATC |
QC10BX02
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NDF-RT |
N0000175589
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WHO-VATC |
QC10BA03
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WHO-VATC |
QC10AA03
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WHO-ATC |
C10BA03
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LIVERTOX |
791
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WHO-ATC |
C10BX02
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WHO-ATC |
C10AA03
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NDF-RT |
N0000000121
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NCI_THESAURUS |
C1655
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EU-Orphan Drug |
EU/3/10/748
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54687
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81093-37-0
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2953
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DB00175
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PRAVASTATIN
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D017035
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SUB10004MIG
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81093-37-0
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6070
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CHEMBL1144
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42463
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81093-37-0
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C62070
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81093-37-0
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SALT/SOLVATE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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PROTEIN BINDING | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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Route of Elimination | PHARMACOKINETIC |
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RENAL PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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