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

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
Structure of PRAVASTATIN

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

HIDE SMILES / InChI

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

Description

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
1370.0 nM [IC50]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Pravastatin attenuates lower torso ischaemia-reperfusion-induced lung injury by upregulating constitutive endothelial nitric oxide synthase.
2001 Apr
Baseline characteristics of the diabetic participants in the Antihypertensive and Lipid-Lowering Treatment to Prevent Heart Attack Trial (ALLHAT).
2001 Apr
Therapeutic change of HMG-CoA reductase inhibitors in patients with coronary artery disease.
2001 Apr
Mevastatin, an HMG-CoA reductase inhibitor, reduces stroke damage and upregulates endothelial nitric oxide synthase in mice.
2001 Apr
Comparative study of HMG-CoA reductase inhibitors on fibrinogen.
2001 Apr
[Effect on plasma fibrinogen of hypercholesterolaemia treatment with pravastatin].
2001 Apr 15
Assessing the results: phase 1 hyperlipidemia outcomes in 27 health plans.
2001 Apr 16
[Acute coronary syndrome. Early lipid reduction decreases risk of recurrence].
2001 Apr 19
New pharmacologic aspects of CS-866, the newest angiotensin II receptor antagonist.
2001 Apr 19
Reassuring effect of pravastatin on natural killer cell activity in stable renal transplant patients.
2001 Apr 27
Clinical relevance of statins: their role in secondary prevention.
2001 Feb
[Acute coronary syndrome. Statins in the early phase save lives].
2001 Feb 8
Stimulation of inflammatory responses in vitro and in vivo by lipophilic HMG-CoA reductase inhibitors.
2001 Jan
Statin therapy and the prevention of dementia.
2001 Jun
Safety and efficacy of pravastatin therapy for the prevention of hyperlipidemia in pediatric and adolescent cardiac transplant recipients.
2001 Jun
Simvastatin-associated memory loss.
2001 Jun
HMG-CoA reductase inhibitors prevent migration of human coronary smooth muscle cells through suppression of increase in oxidative stress.
2001 Jun
Effect of lovastatin, an HMG CoA reductase inhibitor, on acute renal allograft rejection.
2001 Jun
Statins selectively inhibit leukocyte function antigen-1 by binding to a novel regulatory integrin site.
2001 Jun
Fluvastatin suppresses oxidative stress and fibrosis in the interstitium of mouse kidneys with unilateral ureteral obstruction.
2001 Jun
Randomized clinical trials and recent patterns in the use of statins.
2001 Jun
The pravastatin inflammation CRP evaluation (PRINCE): rationale and design.
2001 Jun
PRINCE's prospects: statins, inflammation, and coronary risk.
2001 Jun
Human liver-specific organic anion transporter, LST-1, mediates uptake of pravastatin by human hepatocytes.
2001 Jun
Limitation of heart growth in neonatal piglets by simvastatin and atorvastatin: comparison with pravastatin.
2001 Jun
Compactin enhances osteogenesis in murine embryonic stem cells.
2001 Jun 8
[PATE Study [Pravastatin anti-Atherosclerosis Trial in the Elderly Study]].
2001 Mar
[CARE[ Cholesterol and Recurrent Events Trial]].
2001 Mar
[REGRESS [The Regression Growth Evaluation Statin Study]].
2001 Mar
[LIPID study [Long-term Intervention with Pravastatin in Ischaemic Disease study]].
2001 Mar
[WOSCOPS [West of Scotland Coronary Prevention Study]].
2001 Mar
Is a statin a statin?
2001 Mar
Role of fibrates and HMG-CoA reductase inhibitors in gallstone formation: epidemiological study in an unselected population.
2001 Mar
[Effects of pravastatin in 3260 patients with unstable angina: results from the LIPID study].
2001 Mar
[Treatment with statins for the reduction of cardiovascular risk].
2001 Mar
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
Dementia and statins.
2001 Mar 17
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
Statin induced myopathy does not show up in MIBI scintigraphy.
2001 May
[Pravastatin and the development of diabetes mellitus. Evidence for a protective treatment effect in the West of Scotland Coronary Prevention Study].
2001 May
What do the statin trials tell us?
2001 May
The in vitro inhibitory effect of tannin derivatives on 3-hydroxy-3-methylglutaryl-coenzyme a reductase on vero cells.
2001 May
Interactions of leptin and thyrotropin 24-hour secretory profiles in short normal children.
2001 May
Effects of 1-year treatment with fluvastatin or pravastatin on bone.
2001 May
Cost-effectiveness of pravastatin therapy for survivors of myocardial infarction with average cholesterol levels.
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
[Statins as new therapeutic possibility in osteoporosis?].
2001 May 11
Summaries for patients. Benefits of lowering cholesterol levels in older patients.
2001 May 15
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
Synthesis and biological evaluations of condensed pyridine and condensed pyrimidine-based HMG-CoA reductase inhibitors.
2001 May 21
Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Mon Oct 21 20:59:10 UTC 2019
Edited
by admin
on Mon Oct 21 20:59:10 UTC 2019
Record UNII
KXO2KT9N0G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRAVASTATIN
EMA EPAR   INN   VANDF   WHO-DD  
INN  
Official Name English
PRAVASTATIN [EMA EPAR]
Common Name English
C10AA03
Code English
PRAVASTATIN [INN]
Common Name English
PRAVASTATIN [WHO-DD]
Common Name English
PRAVASTATIN [VANDF]
Common Name English
PRAVATOR
Brand Name English
Classification Tree Code System Code
WHO-VATC QC10BX02
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
NDF-RT N0000175589
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
WHO-VATC QC10BA03
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
WHO-VATC QC10AA03
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
WHO-ATC C10BA03
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
LIVERTOX 791
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
WHO-ATC C10BX02
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
WHO-ATC C10AA03
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
NDF-RT N0000000121
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
NCI_THESAURUS C1655
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
EU-Orphan Drug EU/3/10/748
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
Code System Code Type Description
PUBCHEM
54687
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
CAS
81093-37-0
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
IUPHAR
2953
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
DRUG BANK
DB00175
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
WIKIPEDIA
PRAVASTATIN
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
MESH
D017035
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
EVMPD
SUB10004MIG
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
EPA CompTox
81093-37-0
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
INN
6070
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
ChEMBL
CHEMBL1144
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
RXCUI
42463
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY RxNorm
LactMed
81093-37-0
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
NCI_THESAURUS
C62070
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
HSDB
81093-37-0
Created by admin on Mon Oct 21 20:59:10 UTC 2019 , Edited by admin on Mon Oct 21 20:59:10 UTC 2019
PRIMARY
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ORAL BIOAVAILABILITY PHARMACOKINETIC
Route of Elimination PHARMACOKINETIC RENAL
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