Structure via PubChem · Public domain (PubChem)
(RS)-pioglitazone
Sign in to saveAlso known as 5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione, (+-)-5-({4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl}methyl)-2,4-thiazolidinedione, 5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)thiazolidine-2,4-dione, pioglitazone
Pioglitazone, sold under the brand name Actos among others, is an anti-diabetic medication used to treat type 2 diabetes. It may be used with metformin, a sulfonylurea, or insulin. Use is recommended together with exercise and diet. It is not recommended in type 1 diabetes. It is taken by mouth.
Chemical data
- Formula
- C19H20N2O3S
- Molecular weight
- 356.4 g/mol
- IUPAC name
- 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
- SMILES
- CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3
- InChIKey
- HYAFETHFCAUJAY-UHFFFAOYSA-N
- XLogP
- 3.8
- Polar surface area
- 93.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1999
- Admin. routes
- oral
- Indications
- metabolic syndrome, acute myeloid leukemia, cardiovascular disease, chronic myelogenous leukemia
via ChEMBL · EBI
Research
23 papers- Model-Based Meta-Analysis of the Relationship Between Pioglitazone and Histological Outcomes in Metabolic Dysfunction-Associated Steatohepatitis Patients.CPT: pharmacometrics & systems pharmacology · 2026
- Chemopreventive effects of pioglitazone on chemically induced lung carcinogenesis in mice.Molecular cancer therapeutics · 2010
- Overcoming β-Cell Dysfunction in Type 2 Diabetes Mellitus: CD36 Inhibition and Antioxidant System.Diabetes & metabolism journal · 2025
- Preparation of polymer microspheres capable for pioglitazone release to modify macrophages function.Regenerative therapy · 2019
- Evaluation of PXL065 - deuterium-stabilized (R)-pioglitazone in patients with NASH: A phase II randomized placebo-controlled trial (DESTINY-1).Journal of hepatology · 2023
via PubMed
Wikidata facts
- Subclass of
- glitazone
- Mass
- 356.119464
- Has use
- medication
Show 6 more facts
- chemical formula
- C₁₉H₂₀N₂O₃S
- canonical SMILES
- CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3
- subject has role
- anti-diabetic medication
- World Health Organisation international non-proprietary name
- pioglitazone
- defined daily dose
- 30
- Commons category
- Pioglitazone
Sources (7)
via Wikidata · CC0
~9 min read
Encyclopedic overview
16 sectionsContents
- Medical uses
- Contraindications
- Side effects
- Bladder cancer
- Drug interactions
- Mechanism of action
- Society and culture
- Economics
- Brand names
- Research
- Psychiatry
- Bipolar disorder
- Major depression
- Other illnesses
- See also
- References
Pioglitazone, sold under the brand name Actos among others, is an anti-diabetic medication used to treat type 2 diabetes. It may be used with metformin, a sulfonylurea, or insulin. Use is recommended together with exercise and diet. It is not recommended in type 1 diabetes. It is taken by mouth.
Common side effects include headaches, muscle pains, inflammation of the throat, and swelling. Serious side effects may include bladder cancer, low blood sugar, heart failure, and osteoporosis. Use is not recommended in pregnancy or breastfeeding. It is in the thiazolidinedione (TZD) class and works by improving sensitivity of tissues to insulin.
Excerpted from Wikipedia’s “(RS)-pioglitazone” article, available under the CC BY-SA 4.0 licence.