Pioglitazone

Pioglitazone
Clinical data
Trade namesActos, others
AHFS/Drugs.comMonograph
MedlinePlusa699016
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
Drug classThiazolidinedione
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only[1]
  • EU: Rx-only[2]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding>99%
MetabolismLiver (CYP2C8)
Elimination half-life3–7 hours
ExcretionBile duct
Identifiers
IUPAC name
  • (RS)-5-(4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl)thiazolidine-2,4-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.114.441
Chemical and physical data
FormulaC19H20N2O3S
Molar mass356.44 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point183 to 184 °C (361 to 363 °F)
SMILES
  • O=C1NC(=O)SC1Cc3ccc(OCCc2ncc(cc2)CC)cc3
InChI
  • InChI=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) Y
  • Key:HYAFETHFCAUJAY-UHFFFAOYSA-N Y
  (verify)

Pioglitazone, sold under the brand name Actos among others, is an anti-diabetic medication used to treat type 2 diabetes.[3] It may be used with metformin, a sulfonylurea, or insulin.[3][4] Use is recommended together with exercise and diet.[4] It is not recommended in type 1 diabetes.[4] It is taken by mouth.[4]

Common side effects include headaches, muscle pains, inflammation of the throat, and swelling.[4] Serious side effects may include bladder cancer, low blood sugar, heart failure, and osteoporosis.[4][3] Use is not recommended in pregnancy or breastfeeding.[3] It is in the thiazolidinedione (TZD) class and works by improving sensitivity of tissues to insulin.[3]

Pioglitazone was patented in 1985, and came into medical use in 1999.[5] It is available as a generic medication.[3] In 2022, it was the 120th most commonly prescribed medication in the United States, with more than 5 million prescriptions.[6][7] It was withdrawn in France and Germany in 2011.[8][9][10]

  1. ^ Cite error: The named reference Actos FDA label was invoked but never defined (see the help page).
  2. ^ "Actos EPAR". European Medicines Agency (EMA). 13 October 2000. Retrieved 27 August 2024.
  3. ^ a b c d e f British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 694. ISBN 9780857113382.
  4. ^ a b c d e f "Pioglitazone Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 15 August 2020. Retrieved 3 March 2019.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 450. ISBN 9783527607495. Archived from the original on 21 December 2020. Retrieved 23 September 2020.
  6. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  7. ^ "Pioglitazone Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  8. ^ Burant C (2012). Medical Management of Type 2 Diabetes. American Diabetes Association. p. 63. ISBN 9781580404570. Archived from the original on 28 January 2021. Retrieved 23 September 2020.
  9. ^ Cite error: The named reference FDA safety was invoked but never defined (see the help page).
  10. ^ "Update on ongoing European review of pioglitazone–containing medicines". European Medicines Agency (EMA) (Press release). Archived from the original on 22 October 2020. Retrieved 8 November 2020.
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