Pravastatin

Identification

Summary

Pravastatin is an HMG-CoA reductase inhibitor used to lower lipid levels and to reduce the risk of cardiovascular events, including myocardial infarction and stroke.

Generic Name
Pravastatin
DrugBank Accession Number
DB00175
Background

Pravastatin is the 6-alpha-hydroxy acid form of mevastatin.11 Pravastatin was firstly approved in 1991 becoming the second available statin in the United States. It was the first statin administered as the active form and not as a prodrug.10 This drug was developed by Sankyo Co. Ltd.; however, the first approved pravastatin product was developed by Bristol Myers Squibb and FDA approved in 1991.14

Pravastatin is made through a fermentation process in which mevastatin is first obtained. The manufacturing process is followed by the hydrolysis of the lactone group and the biological hydroxylation with Streptomyces carbophilus to introduce the allylic 6-alcohol group.12

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 424.5277
Monoisotopic: 424.246103506
Chemical Formula
C23H36O7
Synonyms
  • (+)-(3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(S)-2-methylbutyryl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphthyl]heptanoic acid
  • Pravastatin
  • Pravastatin acid
  • Pravastatina
  • Pravastatine
  • Pravastatinum

Pharmacology

Indication

Pravastatin is indicated for primary prevention of coronary events hypercholesterolemic patients without clinical evidence of coronary heart disease. Its use includes the reduction of risk on myocardial infarction, undergoing myocardial revascularization procedures and cardiovascular mortality.10

As well, pravastatin can be used as a secondary prevention agent for cardiovascular events in patients with clinically evident coronary heart disease. This indication includes the reduction of risk of total mortality by reducing coronary death, myocardial infarction, undergoing myocardial revascularization procedures, stroke, and stroke/transient ischemic attack as well as to slow the progression of coronary atherosclerosis.10

The term cardiovascular events correspond to all the incidents that can produce damage to the heart muscle including the interruption of blood flow.15

As adjunctive therapy to diet, pravastatin is used in:

  • Patients with primary hypercholesterolemia and mixed dyslipidemias including hyperlipidemia type IIa and IIb.
  • Patients with elevated serum triglycerides including type IV hyperlipidemia.
  • Patients with heterozygous familial hypercholesterolemia in patients over 8 years of age with low-density lipoprotein (LDL) cholesterol higher than 190 mg/dl after diet modifications or LDL levels higher than 160 mg/dl and familial history of premature cardiovascular diseases or at least two cardiovascular risk factors.10

In patients that do not respond adequately to diet, pravastatin is used to treat patients with primary dysbetalipoproteinemia (type III hyperlipidemia).10

Dyslipidemia is defined as an elevation of plasma cholesterol, triglycerides or both as well as to the presence of low levels of high-density lipoprotein. This condition represents an increased risk for the development of atherosclerosis.16

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Prevention ofAcute coronary events••••••••••••••••••••••••••••••••••••••
Used as adjunct in combination to preventCardiovascular outcomeCombination Product in combination with: Acetylsalicylic acid (DB00945)••• ••••••••••••••••••• •••••••• ••••••••••••••• •••••••
Prevention ofCoronary atherosclerosis•••••••••••••••••••• ••••• •••••••••••••
Prevention ofCoronary death••••••••••••••••••
Treatment ofDysbetalipoproteinemia•••••••••••••••••••••• •••••••• •• ••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

The action of pravastatin on the 3-hydroxy-3-methyl-glutaryl-coenzyme A (HMG-CoA) reductase produces an increase in the expression of hepatic LDL receptors which in order decreases the plasma levels of LDL cholesterol.10

The effect of pravastatin has been shown to significantly reduce the circulating total cholesterol, LDL cholesterol, and apolipoprotein B. As well, it modestly reduces very low-density-lipoproteins (VLDL) cholesterol and triglycerides while increasing the level of high-density lipoprotein (HDL) cholesterol and apolipoprotein A.17

In clinical trials with patients with a history of myocardial infarction or angina with high total cholesterol, pravastatin decreased the level of total cholesterol by 18%, decreased of LDL by 27%, decreased of triglycerides by 6% and increased of high-density lipoprotein (HDL) by 4%. As well, there was reported a decrease in risk of death due to coronary disease of 24%.1

When coadministered with cholestyramine, pravastatin can reduce by 50% the levels of LDL and slow the progression of atherosclerosis and the risk of myocardial infarction and death.10

Mechanism of action

Pravastatin is a specific inhibitor of the hepatic HMG-CoA reductase in humans.10 The inhibition of this enzyme produces a reduction in cholesterol biosynthesis as HMG-CoA reductase activity is an early-limiting step in cholesterol biosynthesis.6

The inhibitory mechanism of action produces a reduction in cholesterol synthesis which in order has been observed to increase the number of LDL receptors on cell surfaces and an enhancement in receptor-mediated metabolism of LDL and clearance.5

On the other hand, pravastatin-driven inhibition of LDL production inhibits hepatic synthesis of VLDL as the LDL is the precursor for these molecules.7

TargetActionsOrganism
A3-hydroxy-3-methylglutaryl-coenzyme A reductase
inhibitor
Humans
UHistone deacetylase 2
inhibitor
Humans
Absorption

Pravastatin is absorbed 60-90 min after oral administration and it presents a low bioavailability of 17%.2 This low bioavailability can be presented due to the polar nature of pravastatin which produces a high range of first-pass metabolism and incomplete absorption.12

Pravastatin is rapidly absorbed from the upper part of the small intestine via proton-coupled carrier-mediated transport to be later taken up in the livery by the sodium-independent bile acid transporter.4 The reported time to reach the peak serum concentration in the range of 30-55 mcg/L is of 1-1.5 hours with an AUC ranging from 60-90 mcg.h/L.8

Volume of distribution

The reported steady-state volume of distribution of pravastatin is reported to be of 0.5 L/kg.9 This pharmacokinetic parameter in children was found to range from 31-37 ml/kg.8

Protein binding

Due its polarity, pravastatin binding to plasma proteins is very limited and the bound form represents only about 43-48% of the administered dose. However, the activity of p-glycoprotein in luminal apical cells and OATP1B1 produce significant changes to pravastatin distribution and elimination.1

Metabolism

After initial administration, pravastatin undergoes extensive first-pass extraction in the liver.2 However, pravastatin's metabolism is not related to the activity of the cytochrome P-450 isoenzymes and its processing is performed in a minor extent in the liver. Therefore, this drug is highly exposed to peripheral tissues.1

The metabolism of pravastatin is ruled mainly by the presence of glucuronidation reactions with very minimal intervention of CYP3A enzymes. After metabolism, pravastatin does not produce active metabolites.2 This metabolism is mainly done in the stomach followed by a minor portion of renal and hepatic processing.4

The major metabolite formed as part of pravastatin metabolism is the 3-alpha-hydroxy isomer. The activity of this metabolite is very clinically negligible.17

Hover over products below to view reaction partners

Route of elimination

From the administered dose of pravastatin, about 70% is eliminated in the feces while about 20% is obtained in the urine.13

When pravastatin is administered intravenously, approximately 47% of the administered dose is eliminated via the urine with 53% of the dose eliminated either via biotransformation of biliary.17

Half-life

The reported elimination half-life of pravastatin is reported to be of 1.8 hours.2

Clearance

The reported clearance rate of pravastatin ranges from 6.3-13.5 ml.min/kg in adults9 while in children it has been reported to be of 4-11 L/min.8

Adverse Effects
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Toxicity

The reported oral LD50 of pravastatin in mice is of 8939 mg/kg.MSDS There haven't been significant overdosage reports however, in the case of overdosage, symptomatic treatment is recommended along with laboratory monitoring and supportive measures.Label

In carcinogenic studies, high dose administration of pravastatin has been reported to increase the incidence of hepatocellular carcinomas in males and lung carcinomas in females. There is no evidence relating the administration of pravastatin with mutagenicity in different assays not to produce effects in fertility or reproductive potential.Label

Pathways
PathwayCategory
Pravastatin 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 pravastatin.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 pravastatin.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbemaciclibPravastatin may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
AbrocitinibThe serum concentration of Pravastatin can be increased when it is combined with Abrocitinib.
AcamprosateThe excretion of Acamprosate can be decreased when combined with Pravastatin.
AcenocoumarolThe risk or severity of bleeding can be increased when Pravastatin is combined with Acenocoumarol.
AcetylcysteineThe excretion of Pravastatin can be decreased when combined with Acetylcysteine.
Food Interactions
  • Take with or without food. Lipid lowering effects are similar in the fasting and fed state.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Pravastatin sodium3M8608UQ6181131-70-6VWBQYTRBTXKKOG-IYNICTALSA-M
Product Images
International/Other Brands
Elisor (Baowei Technology Group) / Lipostat (Bristol-Myers Squibb) / Mevalotin (Daiichi Sankyo) / Pravaselect / Selipran (Bristol-Myers Squibb)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act PravastatinTablet20 mgOralActavis Pharma Company2003-12-092018-06-26Canada flag
Act PravastatinTablet40 mgOralActavis Pharma Company2003-12-092018-06-26Canada flag
Act PravastatinTablet10 mgOralActavis Pharma Company2003-12-092018-06-26Canada flag
Bio PravastatinTablet40 mgOralBioenhance Medicines Inc.2001-07-122003-02-27Canada flag
Bio PravastatinTablet20 mgOralBioenhance Medicines Inc.2001-07-122003-02-27Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ach-pravastatinTablet20 mgOralAccord Healthcare Inc2020-02-24Not applicableCanada flag
Ach-pravastatinTablet10 mgOralAccord Healthcare Inc2019-12-11Not applicableCanada flag
Ach-pravastatinTablet40 mgOralAccord Healthcare Inc2020-02-24Not applicableCanada flag
Ag-pravastatinTablet10 mgOralAngita Pharma Inc.2020-01-13Not applicableCanada flag
Ag-pravastatinTablet40 mgOralAngita Pharma Inc.2019-12-04Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Pal-pravastatin-asaPravastatin sodium (10 mg) + Acetylsalicylic acid (81 mg)Kit; Tablet; Tablet, delayed releaseOralPaladin Labs Inc2006-01-132015-07-31Canada flag
Pal-pravastatin-asaPravastatin sodium (40 mg) + Acetylsalicylic acid (81 mg)Kit; Tablet; Tablet, delayed releaseOralPaladin Labs Inc2006-01-132015-07-31Canada flag
Pal-pravastatin-asaPravastatin sodium (20 mg) + Acetylsalicylic acid (81 mg)Kit; Tablet; Tablet, delayed releaseOralPaladin Labs Inc2006-01-132015-07-31Canada flag
PRAVAFEN HARD CAPSULES 40mg/160mgPravastatin sodium (40 mg) + Fenofibrate (160 mg)CapsuleOralHYPHENS PHARMA PTE. LTD.2014-02-21Not applicableSingapore flag
PRAVAFEN® CAPSULASPravastatin sodium (40 mg) + Fenofibrate (160 mg)Capsule, coatedOralALTADIS FARMACEUTICA S.A.S.2018-03-10Not applicableColombia flag

Categories

ATC Codes
C10AA03 — PravastatinC10BA11 — Pravastatin and ezetimibeC10BA03 — Pravastatin and fenofibrateC10BA12 — Pravastatin, ezetimibe and fenofibrateC10BX02 — Pravastatin and acetylsalicylic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Hydroxy acids and derivatives
Sub Class
Medium-chain hydroxy acids and derivatives
Direct Parent
Medium-chain hydroxy acids and derivatives
Alternative Parents
Fatty alcohols / Medium-chain fatty acids / Hydroxy fatty acids / Fatty acid esters / Branched fatty acids / Beta hydroxy acids and derivatives / Dicarboxylic acids and derivatives / Secondary alcohols / Carboxylic acid esters / Carboxylic acids
show 3 more
Substituents
Alcohol / Aliphatic homopolycyclic compound / Beta-hydroxy acid / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Fatty acid ester
show 10 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
statin (semi-synthetic), carboxylic ester, secondary alcohol, 3-hydroxy carboxylic acid, hydroxy monocarboxylic acid, carbobicyclic compound (CHEBI:63618)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
KXO2KT9N0G
CAS number
81093-37-0
InChI Key
TUZYXOIXSAXUGO-PZAWKZKUSA-N
InChI
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
IUPAC Name
(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
SMILES
[H][C@]12[C@H](C[C@H](O)C=C1C=C[C@H](C)[C@@H]2CC[C@@H](O)C[C@@H](O)CC(O)=O)OC(=O)[C@@H](C)CC

References

Synthesis Reference
US6204032
General References
  1. Salna MP, Singer HM, Dana AN: Pravastatin-Induced Eczematous Eruption Mimicking Psoriasis. Case Rep Dermatol Med. 2017;2017:3418204. doi: 10.1155/2017/3418204. Epub 2017 Jul 31. [Article]
  2. Chastain DB, Stover KR, Riche DM: Evidence-based review of statin use in patients with HIV on antiretroviral therapy. J Clin Transl Endocrinol. 2017 Feb 22;8:6-14. doi: 10.1016/j.jcte.2017.01.004. eCollection 2017 Jun. [Article]
  3. Fitzpatrick T, Perrier L, Tricco AC, Straus SE, Juni P, Zwarenstein M, Lix LM, Smith M, Rosella LC, Henry DA: Protocol for a scoping review of post-trial extensions of randomised controlled trials using individually linked administrative and registry data. BMJ Open. 2017 Feb 17;7(2):e013770. doi: 10.1136/bmjopen-2016-013770. [Article]
  4. Hatanaka T: Clinical pharmacokinetics of pravastatin: mechanisms of pharmacokinetic events. Clin Pharmacokinet. 2000 Dec;39(6):397-412. doi: 10.2165/00003088-200039060-00002. [Article]
  5. Ye YC, Zhao XL, Zhang SY: Use of atorvastatin in lipid disorders and cardiovascular disease in Chinese patients. Chin Med J (Engl). 2015 Jan 20;128(2):259-66. doi: 10.4103/0366-6999.149226. [Article]
  6. McIver LA, Siddique MS: Atorvastatin . [Article]
  7. Ray SK, Rege NN: Atorvastatin: in the management of hyperlipidaemia. J Postgrad Med. 2000 Jul-Sep;46(3):242-3. [Article]
  8. Wiersma HE, Wiegman A, Koopmans RP, Bakker HD, Kastelein JJ, van Boxtel CJ: Steady-state pharmacokinetics of pravastatin in children with familial hypercholesterolaemia. Clin Drug Investig. 2004;24(2):113-20. doi: 10.2165/00044011-200424020-00006. [Article]
  9. Singhvi SM, Pan HY, Morrison RA, Willard DA: Disposition of pravastatin sodium, a tissue-selective HMG-CoA reductase inhibitor, in healthy subjects. Br J Clin Pharmacol. 1990 Feb;29(2):239-43. [Article]
  10. Frishman W., Cheng-Lai A. and Nawarskas J. (2005). Current cardiovascular drugs (4th ed.). Current medicine LLC. [ISBN:1-57340-221-4]
  11. William H. Frishman, MD, Domenic A. Sica, MD (2011). Cardiovascular Pharmacotherapeutics. Cardiotext Publishing. [ISBN:9781935395621]
  12. Taylor JB, Triggle DJ. (2007). Comprehensive Medicinal Chemistry II. Elsevier.
  13. Lemke T., Williams D., Roche V. and Zito W. (2008). Foye's Principles of Medicinal Chemistry (6th) (6th ed.). Lippincott Williams & Wilkins. [ISBN:978-0-7817-6879-5]
  14. FDA approvals [Link]
  15. Chemocare [Link]
  16. Merck Manuals [Link]
  17. PRAVACHOL (pravastatin) monograph [File]
Human Metabolome Database
HMDB0005022
KEGG Drug
D08410
KEGG Compound
C01844
PubChem Compound
54687
PubChem Substance
46504851
ChemSpider
49398
BindingDB
20688
RxNav
42463
ChEBI
63618
ChEMBL
CHEMBL1144
ZINC
ZINC000003798763
Therapeutic Targets Database
DAP000550
PharmGKB
PA451089
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pravastatin
FDA label
Download (251 KB)
MSDS
Download (23.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAutosomal Dominant Polycystic Kidney Disease (ADPKD)1
4CompletedPreventionAcute Coronary Syndrome (ACS)1
4CompletedPreventionAging / Alzheimer's Disease (AD)1
4CompletedPreventionCardiovascular Disease (CVD)1
4CompletedPreventionHyperlipidemias1

Pharmacoeconomics

Manufacturers
  • Bristol myers squibb
  • Apotex corp
  • Dr reddys laboratories inc
  • Glenmark generics ltd
  • Lek pharmaceuticals dd
  • Lupin pharmaceuticals inc
  • Matrix laboratories ltd
  • Mylan pharmaceuticals inc
  • Pliva hrvatska doo
  • Ranbaxy laboratories ltd
  • Teva pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • Watson laboratories inc
  • Zydus pharmaceuticals usa inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • Cadila Healthcare Ltd.
  • Cardinal Health
  • Cobalt Pharmaceuticals Inc.
  • Comprehensive Consultant Services Inc.
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • E.R. Squibb and Sons LLC
  • Glenmark Generics Ltd.
  • International Laboratories Inc.
  • Kaiser Foundation Hospital
  • Lek Pharmaceuticals Inc.
  • Lupin Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Ohm Laboratories Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Vangard Labs Inc.
  • Zydus Pharmaceuticals
Dosage Forms
FormRouteStrength
Capsule, liquid filledOral10 mg
Tablet; tablet, film coatedOral10 MG
Tablet, film coatedOral20 MG
Kit; tablet; tablet, delayed releaseOral
Tablet, coatedOral20 mg
TabletOral10 mg/1
TabletOral80 mg
CapsuleOral
CapsuleOral160 mg
Capsule, coatedOral
TabletOral
TabletOral30 MG
Tablet, film coatedOral40 MG
Tablet, film coatedOral10 MG
TabletOral20 mg/1
TabletOral40 mg/1
TabletOral80 mg/1
TabletOral10 MG
Tablet, film coatedOral
Tablet, coatedOral10 mg
KitOral
Tablet
Tablet, coatedOral40 mg
TabletOral5.000 mg
TabletOral10.00 mg
TabletOral10.000 mg
TabletOral10. mg
TabletOral40 mg
TabletOral20 mg
Prices
Unit descriptionCostUnit
Pravachol 40 mg tablet6.53USD tablet
Pravachol 80 mg tablet6.53USD tablet
Pravastatin sodium 40 mg tablet4.89USD tablet
Pravastatin sodium 80 mg tablet4.89USD tablet
Pravachol 20 mg tablet4.39USD tablet
Pravachol 10 mg tablet4.38USD tablet
Pravastatin sodium 20 mg tablet3.33USD tablet
Pravastatin sodium 10 mg tablet3.28USD tablet
Apo-Pravastatin 40 mg Tablet1.42USD tablet
Co Pravastatin 40 mg Tablet1.42USD tablet
Jamp-Pravastatin 40 mg Tablet1.42USD tablet
Mint-Pravastatin 40 mg Tablet1.42USD tablet
Mylan-Pravastatin 40 mg Tablet1.42USD tablet
Novo-Pravastatin 40 mg Tablet1.42USD tablet
Pms-Pravastatin 40 mg Tablet1.42USD tablet
Pravachol 40 mg Tablet1.42USD tablet
Ran-Pravastatin 40 mg Tablet1.42USD tablet
Ratio-Pravastatin 40 mg Tablet1.42USD tablet
Sandoz Pravastatin 40 mg Tablet1.42USD tablet
Apo-Pravastatin 20 mg Tablet1.18USD tablet
Co Pravastatin 20 mg Tablet1.18USD tablet
Jamp-Pravastatin 20 mg Tablet1.18USD tablet
Mint-Pravastatin 20 mg Tablet1.18USD tablet
Mylan-Pravastatin 20 mg Tablet1.18USD tablet
Novo-Pravastatin 20 mg Tablet1.18USD tablet
Pms-Pravastatin 20 mg Tablet1.18USD tablet
Pravachol 20 mg Tablet1.18USD tablet
Ran-Pravastatin 20 mg Tablet1.18USD tablet
Ratio-Pravastatin 20 mg Tablet1.18USD tablet
Sandoz Pravastatin 20 mg Tablet1.18USD tablet
Apo-Pravastatin 10 mg Tablet1.0USD tablet
Co Pravastatin 10 mg Tablet1.0USD tablet
Jamp-Pravastatin 10 mg Tablet1.0USD tablet
Mint-Pravastatin 10 mg Tablet1.0USD tablet
Mylan-Pravastatin 10 mg Tablet1.0USD tablet
Novo-Pravastatin 10 mg Tablet1.0USD tablet
Pms-Pravastatin 10 mg Tablet1.0USD tablet
Pravachol 10 mg Tablet1.0USD tablet
Ran-Pravastatin 10 mg Tablet1.0USD tablet
Ratio-Pravastatin 10 mg Tablet1.0USD tablet
Sandoz Pravastatin 10 mg Tablet1.0USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5622985No1997-04-222014-10-22US flag
CA1323836No1993-11-022010-11-02Canada flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)171.2 - 173°C'MSDS'
boiling point (°C)>600 ºC at 760 mmHg'MSDS'
water solubility10 mg/ml'MSDS'
logP0.59 'MSDS'
pKa4.2Dinnekere V. et al. 2016. Scientifica.
Predicted Properties
PropertyValueSource
Water Solubility0.242 mg/mLALOGPS
logP2.23ALOGPS
logP1.65Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.21Chemaxon
pKa (Strongest Basic)-2.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area124.29 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity113.6 m3·mol-1Chemaxon
Polarizability46.17 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-6194400000-5f7280491acf9312a516
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0uk9-0009000000-967b377abafe64b73071
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0002900000-bd7fd66d793ae64426ff
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-4809000000-0ed5a8797dfc49ecf5af
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-2900000000-91b125182ce5d90f16ab
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-1900000000-e8fc6384260de93c5aa8
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-1900000000-11e99968bc0ba393b6f9
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-4900000000-0e4265e6dc1468c1471d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0002900000-8795ee00dded0ef8be48
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-3709000000-aa45be15af0471c0a46e
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-2900000000-5617409991f5c58e5130
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-2900000000-2bf5c13979a639625d1c
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-2900000000-9a233e521607e82ab7a0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0900000000-2083dfbb67bf2b03ccf9
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0uk9-0009000000-4b2c09a295ba7f3ce41b
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0607900000-e57e263ad3f74bfda195
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fr-0229100000-942bab1aeb9bac926727
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01vk-7027900000-def9f6412b2e7155effd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0avi-1298300000-670b0306b9ea629cd7e1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-4197100000-7db5b53eceeaf9a48fb3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-4049300000-fef8ca7cba4f7be07758
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-006t-4976000000-01e4314beecae41aefa6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-217.9707706
predicted
DarkChem Lite v0.1.0
[M-H]-221.0994706
predicted
DarkChem Lite v0.1.0
[M-H]-219.1882706
predicted
DarkChem Lite v0.1.0
[M-H]-207.93968
predicted
DeepCCS 1.0 (2019)
[M+H]+216.5774706
predicted
DarkChem Lite v0.1.0
[M+H]+223.1904706
predicted
DarkChem Lite v0.1.0
[M+H]+218.8665706
predicted
DarkChem Lite v0.1.0
[M+H]+210.2571
predicted
DeepCCS 1.0 (2019)
[M+Na]+216.3849706
predicted
DarkChem Lite v0.1.0
[M+Na]+220.8024706
predicted
DarkChem Lite v0.1.0
[M+Na]+218.1087706
predicted
DarkChem Lite v0.1.0
[M+Na]+216.02687
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Ye YC, Zhao XL, Zhang SY: Use of atorvastatin in lipid disorders and cardiovascular disease in Chinese patients. Chin Med J (Engl). 2015 Jan 20;128(2):259-66. doi: 10.4103/0366-6999.149226. [Article]
  3. Ray SK, Rege NN: Atorvastatin: in the management of hyperlipidaemia. J Postgrad Med. 2000 Jul-Sep;46(3):242-3. [Article]
  4. Frishman W., Cheng-Lai A. and Nawarskas J. (2005). Current cardiovascular drugs (4th ed.). Current medicine LLC. [ISBN:1-57340-221-4]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transcription factor binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC2
Uniprot ID
Q92769
Uniprot Name
Histone deacetylase 2
Molecular Weight
55363.855 Da
References
  1. Lin YC, Lin JH, Chou CW, Chang YF, Yeh SH, Chen CC: Statins increase p21 through inhibition of histone deacetylase activity and release of promoter-associated HDAC1/2. Cancer Res. 2008 Apr 1;68(7):2375-83. doi: 10.1158/0008-5472.CAN-07-5807. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. Chen C, Mireles RJ, Campbell SD, Lin J, Mills JB, Xu JJ, Smolarek TA: Differential interaction of 3-hydroxy-3-methylglutaryl-coa reductase inhibitors with ABCB1, ABCC2, and OATP1B1. Drug Metab Dispos. 2005 Apr;33(4):537-46. Epub 2004 Dec 22. [Article]
  2. Hsiang B, Zhu Y, Wang Z, Wu Y, Sasseville V, Yang WP, Kirchgessner TG: A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters. J Biol Chem. 1999 Dec 24;274(52):37161-8. [Article]
  3. Matsushima S, Maeda K, Kondo C, Hirano M, Sasaki M, Suzuki H, Sugiyama Y: Identification of the hepatic efflux transporters of organic anions using double-transfected Madin-Darby canine kidney II cells expressing human organic anion-transporting polypeptide 1B1 (OATP1B1)/multidrug resistance-associated protein 2, OATP1B1/multidrug resistance 1, and OATP1B1/breast cancer resistance protein. J Pharmacol Exp Ther. 2005 Sep;314(3):1059-67. Epub 2005 May 18. [Article]
  4. Kameyama Y, Yamashita K, Kobayashi K, Hosokawa M, Chiba K: Functional characterization of SLCO1B1 (OATP-C) variants, SLCO1B1*5, SLCO1B1*15 and SLCO1B1*15+C1007G, by using transient expression systems of HeLa and HEK293 cells. Pharmacogenet Genomics. 2005 Jul;15(7):513-22. [Article]
  5. Sharma P, Holmes VE, Elsby R, Lambert C, Surry D: Validation of cell-based OATP1B1 assays to assess drug transport and the potential for drug-drug interaction to support regulatory submissions. Xenobiotica. 2010 Jan;40(1):24-37. doi: 10.3109/00498250903351013. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. Mougey EB, Feng H, Castro M, Irvin CG, Lima JJ: Absorption of montelukast is transporter mediated: a common variant of OATP2B1 is associated with reduced plasma concentrations and poor response. Pharmacogenet Genomics. 2009 Feb;19(2):129-38. doi: 10.1097/FPC.0b013e32831bd98c. [Article]
  2. Kobayashi D, Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Involvement of human organic anion transporting polypeptide OATP-B (SLC21A9) in pH-dependent transport across intestinal apical membrane. J Pharmacol Exp Ther. 2003 Aug;306(2):703-8. Epub 2003 Apr 30. [Article]
  3. Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human. J Pharmacol Exp Ther. 2004 Feb;308(2):438-45. Epub 2003 Nov 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Chen C, Mireles RJ, Campbell SD, Lin J, Mills JB, Xu JJ, Smolarek TA: Differential interaction of 3-hydroxy-3-methylglutaryl-coa reductase inhibitors with ABCB1, ABCC2, and OATP1B1. Drug Metab Dispos. 2005 Apr;33(4):537-46. Epub 2004 Dec 22. [Article]
  2. Matsushima S, Maeda K, Kondo C, Hirano M, Sasaki M, Suzuki H, Sugiyama Y: Identification of the hepatic efflux transporters of organic anions using double-transfected Madin-Darby canine kidney II cells expressing human organic anion-transporting polypeptide 1B1 (OATP1B1)/multidrug resistance-associated protein 2, OATP1B1/multidrug resistance 1, and OATP1B1/breast cancer resistance protein. J Pharmacol Exp Ther. 2005 Sep;314(3):1059-67. Epub 2005 May 18. [Article]
  3. Salna MP, Singer HM, Dana AN: Pravastatin-Induced Eczematous Eruption Mimicking Psoriasis. Case Rep Dermatol Med. 2017;2017:3418204. doi: 10.1155/2017/3418204. Epub 2017 Jul 31. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. Hsiang B, Zhu Y, Wang Z, Wu Y, Sasseville V, Yang WP, Kirchgessner TG: A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters. J Biol Chem. 1999 Dec 24;274(52):37161-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
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. Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [Article]
  2. Ohtsuki S, Kikkawa T, Mori S, Hori S, Takanaga H, Otagiri M, Terasaki T: Mouse reduced in osteosclerosis transporter functions as an organic anion transporter 3 and is localized at abluminal membrane of blood-brain barrier. J Pharmacol Exp Ther. 2004 Jun;309(3):1273-81. Epub 2004 Feb 4. [Article]
  3. Hasegawa M, Kusuhara H, Sugiyama D, Ito K, Ueda S, Endou H, Sugiyama Y: Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions. J Pharmacol Exp Ther. 2002 Mar;300(3):746-53. [Article]
Kind
Protein
Organism
Humans
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. Yamazaki M, Akiyama S, Ni'inuma K, Nishigaki R, Sugiyama Y: Biliary excretion of pravastatin in rats: contribution of the excretion pathway mediated by canalicular multispecific organic anion transporter. Drug Metab Dispos. 1997 Oct;25(10):1123-9. [Article]
  2. Sasaki M, Suzuki H, Ito K, Abe T, Sugiyama Y: Transcellular transport of organic anions across a double-transfected Madin-Darby canine kidney II cell monolayer expressing both human organic anion-transporting polypeptide (OATP2/SLC21A6) and Multidrug resistance-associated protein 2 (MRP2/ABCC2). J Biol Chem. 2002 Feb 22;277(8):6497-503. Epub 2001 Dec 17. [Article]
  3. Matsushima S, Maeda K, Kondo C, Hirano M, Sasaki M, Suzuki H, Sugiyama Y: Identification of the hepatic efflux transporters of organic anions using double-transfected Madin-Darby canine kidney II cells expressing human organic anion-transporting polypeptide 1B1 (OATP1B1)/multidrug resistance-associated protein 2, OATP1B1/multidrug resistance 1, and OATP1B1/breast cancer resistance protein. J Pharmacol Exp Ther. 2005 Sep;314(3):1059-67. Epub 2005 May 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
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
References
  1. Suzuki M, Suzuki H, Sugimoto Y, Sugiyama Y: ABCG2 transports sulfated conjugates of steroids and xenobiotics. J Biol Chem. 2003 Jun 20;278(25):22644-9. Epub 2003 Apr 7. [Article]
  2. Matsushima S, Maeda K, Kondo C, Hirano M, Sasaki M, Suzuki H, Sugiyama Y: Identification of the hepatic efflux transporters of organic anions using double-transfected Madin-Darby canine kidney II cells expressing human organic anion-transporting polypeptide 1B1 (OATP1B1)/multidrug resistance-associated protein 2, OATP1B1/multidrug resistance 1, and OATP1B1/breast cancer resistance protein. J Pharmacol Exp Ther. 2005 Sep;314(3):1059-67. Epub 2005 May 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
References
  1. Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Symporter activity
Specific Function
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
Gene Name
SLC16A1
Uniprot ID
P53985
Uniprot Name
Monocarboxylate transporter 1
Molecular Weight
53943.685 Da
References
  1. Tamai I, Takanaga H, Maeda H, Ogihara T, Yoneda M, Tsuji A: Proton-cotransport of pravastatin across intestinal brush-border membrane. Pharm Res. 1995 Nov;12(11):1727-32. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
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. Morisawa Y, Takikawa H: Effect of bile acids on the biliary excretion of pravastatin in rats. Hepatol Res. 2009 Jun;39(6):595-600. doi: 10.1111/j.1872-034X.2009.00493.x. Epub 2009 Feb 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. Hsiang B, Zhu Y, Wang Z, Wu Y, Sasseville V, Yang WP, Kirchgessner TG: A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters. J Biol Chem. 1999 Dec 24;274(52):37161-8. [Article]
  2. Link [Link]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48