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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Pravastatin
- Accession Number
- DB00175 (APRD00328)
- Type
- Small Molecule
- Groups
- Approved
- Description
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
- Structure
Structure for Pravastatin (DB00175)
- 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
- Product Ingredients
Ingredient UNII CAS InChI Key Pravastatin sodium 3M8608UQ61 81131-70-6 VWBQYTRBTXKKOG-IYNICTALSA-M - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataAct Pravastatin Tablet Oral Actavis Pharma Company 2003-12-09 2018-06-26 Canada 
Act Pravastatin Tablet Oral Actavis Pharma Company 2003-12-09 2018-06-26 Canada Act Pravastatin Tablet Oral Actavis Pharma Company 2003-12-09 2018-06-26 Canada Bio Pravastatin Tablet Oral Bioenhance Medicines Inc. 2001-07-12 2003-02-27 Canada Bio Pravastatin Tablet Oral Bioenhance Medicines Inc. 2001-07-12 2003-02-27 Canada Bio Pravastatin Tablet Oral Bioenhance Medicines Inc. 2001-07-12 2003-02-27 Canada M-pravastatin Tablet Oral Mantra Pharma Inc Not applicable Not applicable Canada M-pravastatin Tablet Oral Mantra Pharma Inc 2018-12-11 Not applicable Canada M-pravastatin Tablet Oral Mantra Pharma Inc 2018-12-11 Not applicable Canada M-pravastatin Tablet Oral Mantra Pharma Inc 2018-12-11 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataAch-pravastatin Tablet Oral Accord Healthcare Inc Not applicable Not applicable Canada Ach-pravastatin Tablet Oral Accord Healthcare Inc Not applicable Not applicable Canada Ach-pravastatin Tablet Oral Accord Healthcare Inc 2019-12-11 Not applicable Canada Ag-pravastatin Tablet Oral Angita Pharma Inc. 2020-01-13 Not applicable Canada Ag-pravastatin Tablet Oral Angita Pharma Inc. 2019-12-04 Not applicable Canada Ag-pravastatin Tablet Oral Angita Pharma Inc. 2019-12-04 Not applicable Canada Apo-pravastatin Tablet Oral Apotex Corporation 2001-02-27 Not applicable Canada Apo-pravastatin Tablet Oral Apotex Corporation 2001-02-27 Not applicable Canada Apo-pravastatin Tablet Oral Apotex Corporation 2001-02-27 Not applicable Canada Auro-pravastatin Tablet Oral Auro Pharma Inc 2018-05-22 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Pal-pravastatin-asa Pravastatin sodium (40 mg) + Acetylsalicylic acid (81 mg) Kit; Tablet; Tablet, delayed release Oral Paladin Labs Inc 2006-01-13 2015-07-31 Canada Pal-pravastatin-asa Pravastatin sodium (10 mg) + Acetylsalicylic acid (81 mg) Kit; Tablet; Tablet, delayed release Oral Paladin Labs Inc 2006-01-13 2015-07-31 Canada Pal-pravastatin-asa Pravastatin sodium (20 mg) + Acetylsalicylic acid (81 mg) Kit; Tablet; Tablet, delayed release Oral Paladin Labs Inc 2006-01-13 2015-07-31 Canada Pravigard Pac Pravastatin sodium + Acetylsalicylic acid Tablet Bristol-Myers Squibb Company 2006-10-12 2006-10-12 US 
Pravigard Pac Pravastatin sodium + Acetylsalicylic acid Tablet Bristol-Myers Squibb Company 2006-10-12 2006-10-12 US Pravigard Pac Pravastatin sodium + Acetylsalicylic acid Tablet Bristol-Myers Squibb Company 2006-10-12 2006-10-12 US Pravigard Pac Pravastatin sodium + Acetylsalicylic acid Kit Oral Bristol-Myers Squibb Company 2006-10-12 2006-10-12 US Pravigard Pac Pravastatin sodium (40 mg/1) + Acetylsalicylic acid (325 mg/1) Kit Oral E.R. Squibb & Sons, L.L.C. 2006-01-01 2007-04-30 US Pravigard Pac Pravastatin sodium (40 mg/1) + Acetylsalicylic acid (81 mg/1) Kit Oral E.R. Squibb & Sons, L.L.C. 2005-01-01 2006-12-31 US - International/Other Brands
- Elisor (Baowei Technology Group) / Lipostat (Bristol-Myers Squibb) / Mevalotin (Daiichi Sankyo) / Pravaselect / Selipran (Bristol-Myers Squibb)
- Categories
- Agents Causing Muscle Toxicity
- Anticholesteremic Agents
- BCRP/ABCG2 Inhibitors
- BCRP/ABCG2 Substrates
- BSEP/ABCB11 Substrates
- Enzyme Inhibitors
- Hydroxymethylglutaryl-CoA Reductase Inhibitors
- Hypolipidemic Agents
- Lipid Modifying Agents
- Lipid Modifying Agents, Plain
- Lipid Regulating Agents
- Noxae
- OAT1/SLC22A6 inhibitors
- OAT3/SLC22A8 Inhibitors
- OAT3/SLC22A8 Substrates
- OATP1B1/SLCO1B1 Substrates
- OATP1B3 substrates
- P-glycoprotein substrates
- Toxic Actions
- UNII
- KXO2KT9N0G
- CAS number
- 81093-37-0
- Weight
- Average: 424.5277
Monoisotopic: 424.246103506 - Chemical Formula
- C23H36O7
- 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
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
- Associated Conditions
- Acute Coronary Events
- Cardiovascular Outcomes
- Coronary Artery Atherosclerosis
- Coronary Death
- Death
- Dysbetalipoproteinemia
- Heterozygous Familial Hypercholesterolemia
- High Cholesterol
- Hyperlipidemias
- Mixed Dyslipidemias
- Myocardial Infarction
- Myocardial Revascularization
- Secondary prevention cardiovascular event
- Stroke
- Transient Ischaemic Attack (TIA)
- Elevation of serum triglyceride levels
- 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
Target Actions Organism A3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitorHumans UHistone deacetylase 2 inhibitorHumans - 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
- 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
- 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
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Pravastatin Action Pathway Drug action - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Kinesin-like protein KIF6 --- (C;C) / (C;T) C Allele Effect Directly Studied Patients 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 Allele Effect Directly Studied Patients with this genotype have a lesser reduction in LDL cholesterol with pravastatin. Details
Unlock Additional Data
Additional Data Available
Adverse Effects
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn more Additional Data Available
Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- 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.
Drug Interaction Unlock Additional Data(R)-warfarin The risk or severity of bleeding can be increased when Pravastatin is combined with (R)-warfarin. (S)-Warfarin The risk or severity of bleeding can be increased when Pravastatin is combined with (S)-Warfarin. 4-hydroxycoumarin The risk or severity of bleeding can be increased when Pravastatin is combined with 4-hydroxycoumarin. Abemaciclib Pravastatin may decrease the excretion rate of Abemaciclib which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Pravastatin is combined with Acenocoumarol. Acetylcysteine The excretion of Pravastatin can be decreased when combined with Acetylcysteine. Acetylsalicylic acid The excretion of Pravastatin can be decreased when combined with Acetylsalicylic acid. Acipimox Acipimox may increase the myopathic rhabdomyolysis activities of Pravastatin. Acyclovir The excretion of Acyclovir can be decreased when combined with Pravastatin. Adefovir dipivoxil The excretion of Adefovir dipivoxil can be decreased when combined with Pravastatin. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take with or without food. Lipid lowering effects are similar in the fasting and fed state.
References
- Synthesis Reference
- US6204032
- General References
- 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. [PubMed:28831316]
- 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. [PubMed:29067253]
- 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. [PubMed:28213601]
- Hatanaka T: Clinical pharmacokinetics of pravastatin: mechanisms of pharmacokinetic events. Clin Pharmacokinet. 2000 Dec;39(6):397-412. doi: 10.2165/00003088-200039060-00002. [PubMed:11192473]
- 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. [PubMed:25591572]
- McIver LA, Siddique MS: Atorvastatin . [PubMed:28613530]
- Ray SK, Rege NN: Atorvastatin: in the management of hyperlipidaemia. J Postgrad Med. 2000 Jul-Sep;46(3):242-3. [PubMed:11298482]
- 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. [PubMed:17516697]
- 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. [PubMed:2106337]
- Frishman W., Cheng-Lai A. and Nawarskas J. (2005). Current cardiovascular drugs (4th ed.). Current medicine LLC. [ISBN:1-57340-221-4]
- William H. Frishman, MD, Domenic A. Sica, MD (2011). Cardiovascular Pharmacotherapeutics. Cardiotext Publishing. [ISBN:9781935395621]
- Wolpe P. and Howard J. (2007). Comprehensive Medicinal Chemistry II. Elsevier.
- 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]
- FDA approvals [Link]
- Chemocare [Link]
- Merck Manuals [Link]
- PRAVACHOL (pravastatin) monograph [File]
- External Links
- 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
- ATC Codes
- C10AA03 — Pravastatin
- C10AA — HMG CoA reductase inhibitors
- C10A — LIPID MODIFYING AGENTS, PLAIN
- C10 — LIPID MODIFYING AGENTS
- C — CARDIOVASCULAR SYSTEM
- C10BA — HMG CoA reductase inhibitors in combination with other lipid modifying agents
- C10B — LIPID MODIFYING AGENTS, COMBINATIONS
- C10 — LIPID MODIFYING AGENTS
- C — CARDIOVASCULAR SYSTEM
- AHFS Codes
- 24:06.08 — Hmg-coa Reductase Inhibitors
- FDA label
- Download (251 KB)
- MSDS
- Download (23.5 KB)
Clinical Trials
- Clinical Trials
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
Form Route Strength Kit; tablet; tablet, delayed release Oral Tablet Oral 10 mg/1 Tablet Oral 80 mg Tablet Oral Tablet Oral 10 mg Tablet Oral 20 mg Tablet Oral 40 mg Tablet Oral 20 mg/1 Tablet Oral 40 mg/1 Tablet Oral 80 mg/1 Kit Oral Tablet - Prices
Unit description Cost Unit Pravachol 40 mg tablet 6.53USD tablet Pravachol 80 mg tablet 6.53USD tablet Pravastatin sodium 40 mg tablet 4.89USD tablet Pravastatin sodium 80 mg tablet 4.89USD tablet Pravachol 20 mg tablet 4.39USD tablet Pravachol 10 mg tablet 4.38USD tablet Pravastatin sodium 20 mg tablet 3.33USD tablet Pravastatin sodium 10 mg tablet 3.28USD tablet Apo-Pravastatin 40 mg Tablet 1.42USD tablet Co Pravastatin 40 mg Tablet 1.42USD tablet Jamp-Pravastatin 40 mg Tablet 1.42USD tablet Mint-Pravastatin 40 mg Tablet 1.42USD tablet Mylan-Pravastatin 40 mg Tablet 1.42USD tablet Novo-Pravastatin 40 mg Tablet 1.42USD tablet Pms-Pravastatin 40 mg Tablet 1.42USD tablet Pravachol 40 mg Tablet 1.42USD tablet Ran-Pravastatin 40 mg Tablet 1.42USD tablet Ratio-Pravastatin 40 mg Tablet 1.42USD tablet Sandoz Pravastatin 40 mg Tablet 1.42USD tablet Apo-Pravastatin 20 mg Tablet 1.18USD tablet Co Pravastatin 20 mg Tablet 1.18USD tablet Jamp-Pravastatin 20 mg Tablet 1.18USD tablet Mint-Pravastatin 20 mg Tablet 1.18USD tablet Mylan-Pravastatin 20 mg Tablet 1.18USD tablet Novo-Pravastatin 20 mg Tablet 1.18USD tablet Pms-Pravastatin 20 mg Tablet 1.18USD tablet Pravachol 20 mg Tablet 1.18USD tablet Ran-Pravastatin 20 mg Tablet 1.18USD tablet Ratio-Pravastatin 20 mg Tablet 1.18USD tablet Sandoz Pravastatin 20 mg Tablet 1.18USD tablet Apo-Pravastatin 10 mg Tablet 1.0USD tablet Co Pravastatin 10 mg Tablet 1.0USD tablet Jamp-Pravastatin 10 mg Tablet 1.0USD tablet Mint-Pravastatin 10 mg Tablet 1.0USD tablet Mylan-Pravastatin 10 mg Tablet 1.0USD tablet Novo-Pravastatin 10 mg Tablet 1.0USD tablet Pms-Pravastatin 10 mg Tablet 1.0USD tablet Pravachol 10 mg Tablet 1.0USD tablet Ran-Pravastatin 10 mg Tablet 1.0USD tablet Ratio-Pravastatin 10 mg Tablet 1.0USD tablet Sandoz Pravastatin 10 mg Tablet 1.0USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Unlock Additional DataUS5622985 No 1997-04-22 2014-10-22 US CA1323836 No 1993-11-02 2010-11-02 Canada Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 171.2 - 173°C 'MSDS' boiling point (°C) >600 ºC at 760 mmHg 'MSDS' water solubility 10 mg/ml 'MSDS' logP 0.59 'MSDS' pKa 4.2 Dinnekere V. et al. 2016. Scientifica. - Predicted Properties
Property Value Source Water Solubility 0.242 mg/mL ALOGPS logP 2.23 ALOGPS logP 1.65 ChemAxon logS -3.2 ALOGPS pKa (Strongest Acidic) 4.21 ChemAxon pKa (Strongest Basic) -2.7 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 124.29 Å2 ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 113.6 m3·mol-1 ChemAxon Polarizability 46.56 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- 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
- Fatty alcohol / Medium-chain hydroxy acid / Medium-chain fatty acid / Beta-hydroxy acid / Branched fatty acid / Hydroxy fatty acid / Fatty acid ester / Fatty acyl / Dicarboxylic acid or derivatives / Secondary alcohol 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)
Targets
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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. [PubMed:25591572]
- Ray SK, Rege NN: Atorvastatin: in the management of hyperlipidaemia. J Postgrad Med. 2000 Jul-Sep;46(3):242-3. [PubMed:11298482]
- 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
- 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. [PubMed:18381445]
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
- 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. [PubMed:15616150]
- 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. [PubMed:10601278]
- 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. [PubMed:15901800]
- 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. [PubMed:15970799]
- 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. [PubMed:19919292]
- 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
- 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. [PubMed:19151602]
- 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. [PubMed:12724351]
- 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. [PubMed:14610227]
- 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
- 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. [PubMed:15616150]
- 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. [PubMed:15901800]
- 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. [PubMed:28831316]
- 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
- 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. [PubMed:10601278]
- 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
- 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. [PubMed:14978359]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- 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
- 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. [PubMed:14978359]
- 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. [PubMed:14762099]
- 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. [PubMed:11861777]
- 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
- 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. [PubMed:9321514]
- 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. [PubMed:11748225]
- 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. [PubMed:15901800]
- 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
- 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. [PubMed:14978359]
- 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
- 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. [PubMed:12682043]
- 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. [PubMed:15901800]
- 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
- 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. [PubMed:14978359]
- 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
- 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. [PubMed:8592677]
- 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
- 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. [PubMed:19260999]
- 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
- 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. [PubMed:10601278]
- Link [Link]
Drug created on June 13, 2005 07:24 / Updated on March 30, 2020 00:49
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