Editing Pioglitazone (section)

{{Short description|Chemical compound}}
{{Use dmy dates|date=February 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 464207213
| image = Pioglitazone.svg
| width = 271
| alt = 
| chirality = [[Racemic mixture]]
| image2 = Pioglitazone ball and stick from xtal 2017.png
| alt2 =

<!--Clinical data-->
| tradename = Actos, others
| Drugs.com = {{drugs.com|monograph|pioglitazone-hydrochloride}}
| MedlinePlus = a699016
| DailyMedID = Pioglitazone
| pregnancy_AU      = B3
| pregnancy_AU_comment = 
| pregnancy_category= 
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Thiazolidinedione]]
| ATC_prefix = A10
| ATC_suffix = BG03

<!-- Legal status -->
| legal_AU          = S4
| legal_AU_comment  = 
| legal_BR          = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment  = 
| legal_CA          = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment  = 
| legal_DE          = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment  = 
| legal_NZ          = <!-- Class A, B, C -->
| legal_NZ_comment  = 
| legal_UK          = POM
| legal_UK_comment  = 
| legal_US          = Rx-only
| legal_US_comment  = <ref name="Actos FDA label" />
| legal_EU          = Rx-only
| legal_EU_comment  = <ref>{{cite web | title=Actos EPAR | website=European Medicines Agency (EMA) | date=13 October 2000 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/actos | access-date=27 August 2024}}</ref>
| legal_UN          = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment  = 
| legal_status      = Rx-only

<!-- Pharmacokinetic data -->
| protein_bound = &gt;99%
| metabolism = [[Liver]] (CYP2C8)
| elimination_half-life = 3–7 hours
| excretion = [[Bile duct]]

<!--Identifiers-->
| index2_label = as HCl
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 111025-46-8
| PubChem = 4829
| IUPHAR_ligand = 2694
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01132
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4663
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X4OV71U42S
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08378
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D00945
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8228
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 595

<!--Chemical data-->
| IUPAC_name = (''RS'')-5-(4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl)thiazolidine-2,4-dione
| C=19 | H=20 | N=2 | O=3 | S=1
| smiles = O=C1NC(=O)SC1Cc3ccc(OCCc2ncc(cc2)CC)cc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HYAFETHFCAUJAY-UHFFFAOYSA-N
| melting_point = 183
| melting_high = 184
}}

<!-- Definition and uses -->
'''Pioglitazone''', sold under the brand name '''Actos''' among others, is an [[anti-diabetic medication]] used to treat [[type 2 diabetes]].<ref name=BNF76/> It may be used with [[metformin]], a [[sulfonylurea]], or [[insulin]].<ref name=BNF76/><ref name=AHFS2019 /> Use is recommended together with exercise and diet.<ref name=AHFS2019/> It is not recommended in [[type 1 diabetes]].<ref name=AHFS2019/> It is taken [[Oral administration|by mouth]].<ref name=AHFS2019>{{cite web |title=Pioglitazone Hydrochloride Monograph for Professionals |url=https://www.drugs.com/monograph/pioglitazone-hydrochloride.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=3 March 2019 |archive-date=15 August 2020 |archive-url=https://web.archive.org/web/20200815210917/https://www.drugs.com/monograph/pioglitazone-hydrochloride.html |url-status=live }}</ref>

<!-- Side effects and mechanisms -->
Common side effects include headaches, muscle pains, inflammation of the throat, and swelling.<ref name=AHFS2019/> Serious side effects may include [[bladder cancer]], [[low blood sugar]], [[heart failure]], and [[osteoporosis]].<ref name=AHFS2019/><ref name=BNF76/> Use is not recommended in [[pregnancy]] or [[breastfeeding]].<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=694|edition=76}}</ref> It is in the [[thiazolidinedione]] (TZD) class and works by improving sensitivity of tissues to insulin.<ref name=BNF76/>

<!-- History, society, and culture -->
Pioglitazone was patented in 1985, and came into medical use in 1999.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=450 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA450 |access-date=23 September 2020 |archive-date=21 December 2020 |archive-url=https://web.archive.org/web/20201221150549/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA450 |url-status=live }}</ref> It is available as a [[generic medication]].<ref name=BNF76/> In 2022, it was the 120th 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 = Pioglitazone Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Pioglitazone | access-date = 30 August 2024 }}</ref> It was withdrawn in France and Germany in 2011.<ref>{{cite book | vauthors = Burant C |title=Medical Management of Type 2 Diabetes |date=2012 |publisher=American Diabetes Association |isbn=9781580404570 |page=63 |url=https://books.google.com/books?id=b4osDQAAQBAJ&pg=PA63 |access-date=23 September 2020 |archive-date=28 January 2021 |archive-url=https://web.archive.org/web/20210128055302/https://books.google.com/books?id=b4osDQAAQBAJ&pg=PA63 |url-status=live }}</ref><ref name="FDA safety" /><ref>{{cite press release | title=Update on ongoing European review of pioglitazone–containing medicines | website=[[European Medicines Agency]] (EMA) | url=https://www.ema.europa.eu/en/news/update-ongoing-european-review-pioglitazone-containing-medicines | access-date=8 November 2020 | archive-date=22 October 2020 | archive-url=https://web.archive.org/web/20201022125345/https://www.ema.europa.eu/en/news/update-ongoing-european-review-pioglitazone-containing-medicines | url-status=live }}</ref>