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Isosorbide dinitrate
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{{Short description|Chemical compound}} {{Use dmy dates|date=February 2024}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477495637 | image = Isosorbide dinitrate structure.svg | image_class = skin-invert-image | width = 192 | alt = | image2 = Isosorbide-dinitrate-from-xtal-3D-bs-17.png | image_class2 = bg-transparent | alt2 = <!-- Clinical data --> | tradename = Isordil, others<ref name=AHFS2016/> | Drugs.com = {{drugs.com|monograph|isosorbide-dinitrate-mononitrate}} | MedlinePlus = a682348 | DailyMedID = Isosorbide dinitrate | pregnancy_AU = B1 | legal_status = Rx-only | routes_of_administration = [[Oral administration|By mouth]] <!-- Pharmacokinetic data --> | bioavailability = 10β90%, average 25% | metabolism = [[Liver]] | elimination_half-life = 1 hour | excretion = [[Kidney]] <!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 87-33-2 | ATC_prefix = C01 | ATC_suffix = DA08 | ATC_supplemental = {{ATC|C05|AE02}} | PubChem = 6883 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00883 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6619 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 2171310 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = IA7306519N | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D00516 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 6061 | synonyms = ISDN; (3''R'',3a''S'',6''S'',6a''S'')-hexahydrofuro[3,2-''b'']furan-3,6-diyl dinitrate <!-- Chemical data --> | IUPAC_name = 1,4:3,6-dianhydro-2,5-di-''O''-nitro-<small>D</small>-glucitol | C=6 | H=8 | N=2 | O=8 | SMILES = [O-][N+](=O)O[C@H]1[C@H]2OC[C@H](O[N+]([O-])=O)[C@H]2OC1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = MOYKHGMNXAOIAT-JGWLITMVSA-N }} <!-- Definition and medical uses --> '''Isosorbide dinitrate''' is a medication used for [[heart failure]], [[esophageal spasms]], and to treat and prevent [[angina pectoris]].<ref name=AHFS2016/> It has been found to be particularly useful in heart failure due to [[systolic dysfunction]] together with [[hydralazine]].<ref>{{cite journal | vauthors = Chavey WE, Bleske BE, Van Harrison R, Hogikyan RV, Kesterson SK, Nicklas JM | title = Pharmacologic management of heart failure caused by systolic dysfunction | journal = American Family Physician | volume = 77 | issue = 7 | pages = 957β964 | date = April 2008 | pmid = 18441861 }}</ref><ref name=AHFS2016/> It is taken [[Oral administration|by mouth]] or under the tongue.<ref name=AHFS2016>{{cite web|title=Isosorbide Dinitrate/Mononitrate|url=https://www.drugs.com/monograph/isosorbide-dinitrate-mononitrate.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161221004406/https://www.drugs.com/monograph/isosorbide-dinitrate-mononitrate.html|archive-date=21 December 2016}}</ref> <!-- Side effects and mechanism --> Common side effects include [[headache]], [[postural hypotension|lightheadedness with standing]], and [[blurred vision]].<ref name=AHFS2016/> Severe side effects include [[low blood pressure]].<ref name=AHFS2016/> It is unclear if use in [[pregnancy]] is safe for the baby.<ref name=AHFS2016/> It should not be used together with [[PDE5 inhibitor|PDE5 Inhibitors]].<ref name=AHFS2016/> Isosorbide dinitrate is in the [[nitrate (pharmacology)|nitrate]] family of medications and works by [[vasodilation|dilating blood vessels]].<ref name=AHFS2016/> <!-- Society and culture --> Isosorbide dinitrate was first written about in 1939.<ref name=Fis2006>{{cite book| vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9783527607495|page=454|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA454|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220113902/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA454|archive-date=20 December 2016}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> Isosorbide dinitrate is available as a [[generic medication]].<ref name=AHFS2016/><ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. [[Food and Drug Administration]] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=dead }}</ref> A long-acting form exists.<ref name=AHFS2016/> In 2022, isosorbide was the 119th most commonly prescribed medication in the United States, with more than 5{{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 = Isosorbide Drug Usage Statistics, United States, 2013β2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Isosorbide | access-date = 30 August 2024 }}</ref>
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