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Revision as of 14:08, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Saving copy of the {{drugbox}} taken from revid 458450153 of page Pravastatin for the Chem/Drugbox validation project (updated: 'DrugBank').		Latest revision as of 15:50, 19 January 2025 edit Ozzie10aaaa (talk | contribs)Autopatrolled, Extended confirmed users, New page reviewers214,204 editsm Cleaned up using AutoEd
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			{{Short description|Cholesterol lowering medication in the statin class}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
			{{Use dmy dates|date=September 2024}}
	{{Drugbox
			{{cs1 config|name-list-style=vanc|display-authors=6}}
			{{Infobox drug
	| Verifiedfields = changed		| Verifiedfields = changed
	| verifiedrevid = 458448870		| verifiedrevid = 464213376
	| IUPAC_name = (3''R'',5''R'')-3,5-dihydroxy-7-((1''R'',2''S'',6''S'',8''R'',8a''R'')-6-hydroxy-2-methyl-8-{oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-heptanoic acid
	| image = Pravastatin.svg		| image = Pravastatin.svg
	| width = 181		| width = 181
			| alt =
	<!--Clinical data-->		<!-- Clinical data -->
	| tradename = Pravachol		| tradename = Pravachol, others
	| Drugs.com = {{drugs.com|monograph|pravachol}}		| Drugs.com = {{drugs.com|monograph|pravastatin-sodium}}
	| MedlinePlus = a692025		| MedlinePlus = a692025
			| DailyMedID = Pravastatin
	| pregnancy_category = X
	| legal_status =		| pregnancy_AU = D
	| routes_of_administration = oral		| routes_of_administration = ]
			| ATC_prefix = C10
			| ATC_suffix = AA03
			| ATC_supplemental =
	<!--Pharmacokinetic data-->		<!-- Legal status -->
	| bioavailability = 17%		| legal_AU = S4
			| legal_CA = Rx-only
	| protein_bound = 50%
			| legal_UK = POM
	| metabolism = renal and hepatic
			| legal_US = Rx-only
	| elimination_half-life = 1.5-2 hours
			| legal_US_comment = <ref name="Pravastatin FDA label" /><ref>{{cite web | title=Pravachol (pravastatin sodium) Tablets Initial U.S. Approval: 1991 | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=527079 | access-date=2 September 2024}}</ref>
			| legal_EU = Rx-only
			| legal_EU_comment = <ref>{{cite web | title = Active substance: pravastatin | url = https://www.ema.europa.eu/documents/psusa/pravastatin-list-nationally-authorised-medicinal-products-psusa/00002500/202003_en.pdf | work = List of nationally authorised medicinal products | publisher = European Medicines Agency | date = 26 November 2020 }}</ref>
			| legal_status =
	<!--Identifiers-->		<!-- Pharmacokinetic data -->
			| bioavailability = 18%<ref name = PK>{{cite journal | vauthors = Neuvonen PJ, Backman JT, Niemi M | title = Pharmacokinetic comparison of the potential over-the-counter statins simvastatin, lovastatin, fluvastatin and pravastatin | journal = Clinical Pharmacokinetics | volume = 47 | issue = 7 | pages = 463–474 | date = 2008 | pmid = 18563955 | doi = 10.2165/00003088-200847070-00003 | s2cid = 11716425 }}</ref>
	| CASNo_Ref = {{cascite|correct|CAS}}
			| protein_bound = 50%<ref name = PK/>
			| metabolism = ] (minimal)<ref name = PK/>
			| elimination_half-life = 1-3 hours<ref name = PK/>
			<!-- Identifiers -->
			| index2_label = as salt
	| CAS_number_Ref = {{cascite|correct|??}}		| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 81093-37-0		| CAS_number = 81093-37-0
			| CAS_supplemental =
	| ATC_prefix = C10
	| ATC_suffix = AA03
	| ATC_supplemental =
	| PubChem = 54687		| PubChem = 54687
			| IUPHAR_ligand = 2953
	| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB00175		| DrugBank = DB00175
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = KXO2KT9N0G		| UNII = KXO2KT9N0G
			| KEGG_Ref =
			| KEGG = D08410
			| KEGG2_Ref =
			| KEGG2 = D00893
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 63618
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 1144		| ChEMBL = 1144
			| NIAID_ChemDB =
			| PDB_ligand =
			| synonyms =
	<!--Chemical data-->		<!-- Chemical and physical data -->
			| IUPAC_name = (3''R'',5''R'')-3,5-dihydroxy-7-((1''R'',2''S'',6''S'',8''R'',8a''R'')-6-hydroxy-2-methyl-8-{oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-heptanoic acid
	| C=23 | H=36 | O=7
			| C=23 | H=36 | O=7
	| molecular_weight = 424.528 g/mol
	| smiles = O=C(O)C(O)C(O)CC2(/C=C\C1=C\(O)C(OC(=O)(C)CC)12)C		| smiles = O=C(O)C(O)C(O)CC2(/C=C\C1=C\(O)C(OC(=O)(C)CC)12)C
	| InChI = 1/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
	| InChIKey = TUZYXOIXSAXUGO-PZAWKZKUBI
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 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		| StdInChI = 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
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	| StdInChIKey = TUZYXOIXSAXUGO-PZAWKZKUSA-N		| StdInChIKey = TUZYXOIXSAXUGO-PZAWKZKUSA-N
	}}		}}
			<!-- Definition and medical uses -->
			'''Pravastatin''', sold under the brand name '''Pravachol''' among others, is a ] medication, used for preventing ] in those at high risk and treating ].<ref name=AHFS2018/> It is suggested to be used together with diet changes, exercise, and weight loss.<ref name=AHFS2018/> It is taken by mouth.<ref name=AHFS2018>{{cite web |title=Pravastatin Sodium Monograph for Professionals |url=https://www.drugs.com/monograph/pravastatin-sodium.html |website=Drugs.com |publisher=AHFS |access-date=23 December 2018 |language=en}}</ref>
			<!-- Side effects and mechanism -->
			Common side effects include joint pain, diarrhea, nausea, headaches, and muscle pains.<ref name=AHFS2018/> Serious side effects may include ], liver problems, and ].<ref name=AHFS2018/> Use during ] may harm the fetus.<ref name=AHFS2018/> Like all statins, pravastatin works by inhibiting ], an ] found in ] that plays a role in producing ].<ref name=AHFS2018/>
			<!-- Society and culture -->
			Pravastatin was patented in 1980 and approved for medical use in 1989.<ref name=Fis2006>{{cite book| vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9783527607495|page=472|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA472 }}</ref> It is on the ].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> It is available as a ].<ref name=AHFS2018/> In 2022, it was the 37th most commonly prescribed medication in the United States, with more than 16{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Pravastatin Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Pravastatin | access-date = 30 August 2024 }}</ref>
			==Medical uses==
			Pravastatin is primarily used for the treatment of ] and the prevention of ].<ref name=AHFS>{{cite web|title=Pravachol|url=https://www.drugs.com/monograph/pravachol.html|work=The American Society of Health-System Pharmacists|access-date=3 April 2011}}</ref> It is recommended to be used only after other measures, such as diet, exercise, and weight reduction, have not improved cholesterol levels.<ref name=AHFS />
			Pravastatin has been found to have a similar effectiveness at lowering low-density lipoprotein cholesterol as ] but evidence indicates that pravastatin may not be as effective as other ] medications.<ref name="Adams_2023">{{cite journal | vauthors = Adams SP, Alaeiilkhchi N, Tasnim S, Wright JM | title = Pravastatin for lowering lipids | journal = The Cochrane Database of Systematic Reviews | volume = 2023 | issue = 9 | pages = CD013673 | date = September 2023 | pmid = 37721222 | pmc = 10506175 | doi = 10.1002/14651858.CD013673.pub2 | collaboration = Cochrane Hypertension Group }}</ref> The beneficial effect of pravastatin is dependent on the dose and the potential for side effects or unwanted effects from this medication are not clear from clinical trials.<ref name="Adams_2023" />
			==Adverse effects and contraindications==
			Pravastatin has undergone over 112,000 patient-years of double-blind, randomized trials using the 40&nbsp;], once-daily dose and placebos. These trials indicate pravastatin is well tolerated and displays few noncardiovascular abnormalities in patients.<ref name="pmid12021218">{{cite journal | vauthors = Pfeffer MA, Keech A, Sacks FM, Cobbe SM, Tonkin A, Byington RP, Davis BR, Friedman CP, Braunwald E | title = Safety and tolerability of pravastatin in long-term clinical trials: prospective Pravastatin Pooling (PPP) Project | journal = Circulation | volume = 105 | issue = 20 | pages = 2341–2346 | date = May 2002 | pmid = 12021218 | doi = 10.1161/01.cir.0000017634.00171.24 | doi-access = free | author7-link = Barry R. Davis }}</ref>
			]s, conditions that warrant withholding treatment with pravastatin, include pregnancy and breastfeeding.<ref name=RxList>{{cite web| vauthors = Williams E |title=Pravachol Side Effects Center|url=http://www.rxlist.com/pravachol-side-effects-drug-center.htm|publisher=RxList|access-date=1 December 2012}}</ref> Taking pravastatin while pregnant could lead to birth defects. While the amount of pravastatin ingested by an infant from breastfeeding is low, patients breastfeeding should not take pravastatin due to potential effects on the infant's lipid metabolism.<ref name=LactMed>{{cite web|title=Pravastatin|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~MNhuQa:1|work=LactMed|publisher=U.S. National Library of Medicine|access-date=1 December 2012}}{{dead link|date=September 2024}}</ref>
			==Drug interactions==
			Medications that should not be taken with pravastatin include, but are not limited to:<ref name="AHFS"/><ref name=RxList/>
			* ] (Tagamet)
			* ] (Colcrys)
			* ] (Neoral, Sandimmune)
			* ] (Nizoral)
			* Additional cholesterol-lowering medications such as: ] (Tricor), ] (Lopid), ] (Questran, Questran Light, Cholybar), and ] (nicotinic acid, Niacor, Niaspan);
			* Specific ]s such as: ] and ritonavir (Kaletra), and ] (Norvir) taken with ] (Prezista); and ] (Aldactone).
			The combination of ] is approved for use in the European Union.<ref name="Pravafenix EPAR">{{cite web | title=Pravafenix EPAR | website=] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/pravafenix | access-date=25 April 2020}}</ref>
			==Mechanism of action==
			Pravastatin acts as a lipoprotein-lowering drug through two pathways. In the major pathway, pravastatin inhibits the function of ]. As a ] ] inhibitor, pravastatin ] 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 ] to ] 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.<ref name="pmid15313959">{{cite journal | vauthors = Vaughan CJ, Gotto AM | title = Update on statins: 2003 | journal = Circulation | volume = 110 | issue = 7 | pages = 886–892 | date = August 2004 | pmid = 15313959 | doi = 10.1161/01.CIR.0000139312.10076.BA | doi-access = free }}</ref>
			== Pharmacokinetics ==
			Oral bioavailability of pravastatin ranges from 17-34% with peak plasma concentration achieved 1-1.5 hours after administration. Absorption of drug is modestly decreased when taken with food however this does not reduce the clinical lipid-lowering effect.<ref name="Pravastatin FDA label">{{Cite web |title=DailyMed - Pravastatin sodium tablet |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6c011348-a236-47d3-bbef-3e0b956dd080 |access-date=14 January 2024 |website=dailymed.nlm.nih.gov}}</ref>
			The 3α-hydroxyisomeric metabolite of pravastatin is also an active HMG-CoA reductase inhibitor with approximately 2.5-10% the potency of the parent compound. Pravastatin has a plasma half-life of 1.8 hours whereas this active metabolite has a half-life up to 77 hours.<ref name="Pravastatin FDA label" />
			==History==
			Initially known as CS-514, pravastatin is a derivative of ML236B (compactin), which was identified in a fungus called '']'' in the 1970s by researchers of the ]<ref name="pmid12815379">{{cite journal | vauthors = Tobert JA | title = Lovastatin and beyond: the history of the HMG-CoA reductase inhibitors | journal = Nature Reviews. Drug Discovery | volume = 2 | issue = 7 | pages = 517–526 | date = July 2003 | pmid = 12815379 | doi = 10.1038/nrd1112 | s2cid = 3344720 }}</ref> It is being marketed outside ] by the ] ]. In 2005, Pravachol was the 22nd-highest selling brand-name drug in the United States, with sales totaling $1.3 billion.<ref name="fda announcement">{{cite press release |url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2006/ucm108644.htm |title=FDA Approves First Generic Pravastatin |access-date=20 January 2008 |website=] (FDA) |archive-url=https://web.archive.org/web/20100306173645/http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2006/ucm108644.htm |archive-date=6 March 2010 |url-status=dead }}</ref>
			The ] (FDA) approved generic pravastatin for use in the United States in April 2006.<ref name="fda announcement" /> Generic pravastatin sodium tablets were manufactured by ] Ltd, India and Teva Pharmaceuticals in Kfar Sava, Israel.<ref name="fda announcement" />
			== References ==
			{{reflist}}
			{{Statins}}
			{{Portal bar | Medicine}}
			]
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			]