Pioglitazone

Pioglitazone
Clinical data
Trade names	Actos, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699016
License data	US DailyMed: Pioglitazone;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth
Drug class	Thiazolidinedione
ATC code	A10BG03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	>99%
Metabolism	Liver (CYP2C8)
Elimination half-life	3–7 hours
Excretion	Bile duct
Identifiers
	IUPAC name (RS)-5-(4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl)thiazolidine-2,4-dione;
CAS Number	111025-46-8 ;
PubChem CID	4829;
IUPHAR/BPS	2694;
DrugBank	DB01132 ;
ChemSpider	4663 ;
UNII	X4OV71U42S;
KEGG	D08378 ; as HCl: D00945 ;
ChEBI	CHEBI:8228 ;
ChEMBL	ChEMBL595 ;
CompTox Dashboard (EPA)	DTXSID3037129 ;
ECHA InfoCard	100.114.441
Chemical and physical data
Formula	C19H20N2O3S
Molar mass	356.44 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Melting point	183 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) ; Key:HYAFETHFCAUJAY-UHFFFAOYSA-N ;
	(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 2021, it was the 129th most commonly prescribed medication in the United States, with more than 4 million prescriptions.^[6]^[7] It was withdrawn in France and Germany in 2011.^[8]^[9]^[10]

^ Cite error: The named reference Actos FDA label was invoked but never defined (see the help page).
^ "Actos EPAR". European Medicines Agency (EMA). 13 October 2000. Retrieved 27 August 2024.
^ ^a ^b ^c ^d ^e ^f British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 694. ISBN 9780857113382.
^ ^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.
^ 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.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Pioglitazone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
^ 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.
^ Cite error: The named reference FDA safety was invoked but never defined (see the help page).
^ "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.

[Actos_FDA_label-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.

[BNF76-3] ^ ^a ^b ^c ^d ^e ^f British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 694. ISBN 9780857113382.

[AHFS2019-4] ^ ^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 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[7] "Pioglitazone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 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.

[FDA_safety-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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