Pioglitazone

Athanor · official

C₁₉H₂₀N₂O₃S · 356.4 g/mol

IUPAC name: 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

Also called Actos, thiazolidinedione, glitazone

Drugs Rings

Open in Athanor

Drawn from its SMILES with RDKit

WarningHarmful if swallowed, in contact with skin or if inhaled · Harmful if swallowed · Harmful in contact with skin · Causes skin irritation · Causes serious eye irritation · Harmful if inhaled · May cause respiratory irritation · Suspected of causing cancer

Names and identifiers

IUPAC name: 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
Synonyms: Actos, thiazolidinedione, glitazone
+ 35 more
Glustin, Zactos, Pioglitazona, Pioglitazonum, 5-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione, AD-4833, 5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione, CHEBI:8228, X4OV71U42S, U-72107, 5-((4-(2-(5-Ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione, 5-[4-[2-(5-ETHYL-2-PYRIDYL)ETHOXY]BENZYL]-2,4-THIAZOLIDINEDIONE, DTXCID1017129, DTXSID3037129, 5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione, 5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione, 5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione, (+-)-5-((4-(2-(5-ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione, 2,4-Thiazolidinedione, 5-((4-(2-(5-ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-, (+-)-, U72,107A, 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione, 5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)-1,3-thiazolidine-2,4-dione, 5-((4-(2-(5-ethylpyridin-2-yl)ethoxy)phenyl)methyl)-1,3-thiazolidine-2,4-dione, RefChem:56525, A10BG03, AD4833, U72107A, 601-029-7, 921-004-7, Pioglitazonum [INN-Latin], 5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione, Pioglitazona [INN-Spanish], U 72107, MFCD00865504, pioglitazone (INN)
Molecular formula: C₁₉H₂₀N₂O₃S
Empirical formula: C₁₉H₂₀N₂O₃S
Molecular weight: 356.4 g/mol
Exact mass: 356.11946
CAS number: 111025-46-8
PubChem CID: 4829
Canonical SMILES: CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3
Isomeric SMILES: CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3
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)
InChIKey: HYAFETHFCAUJAY-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms: 25
Rings: 3
Aromatic rings: 2
Fraction sp³ carbons (Fsp3): 0.32
H-bond donors: 1
H-bond acceptors: 5
Rotatable bonds: 7
TPSA (Å²): 68.3 computed here · PubChem 93.6
Formal charge: 0
XLogP3: 3.8 PubChem
Complexity: 466 PubChem
Stereocenters: 0 defined, 1 undefinedCIP: C15: undefined
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C64.02%
H5.66%
N7.86%
O13.47%
S9.00%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: 3.16 Crippen (Wildman and Crippen 1999)
log S (water solubility): -3.93 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 2.82 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 356.45
log P ≤ 5 (Crippen): 3.16
H-bond donors ≤ 5: 1
H-bond acceptors ≤ 10: 5

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 6 company reports to ECHA. Source [2].

Harmful or irritant
Health hazard

H302+H312+H332Harmful if swallowed, in contact with skin or if inhaled (16.7% of reports)
H302Harmful if swallowed
H312Harmful in contact with skin (66.7% of reports)
H315Causes skin irritation (16.7% of reports)
H319Causes serious eye irritation (16.7% of reports)
H332Harmful if inhaled (66.7% of reports)
H335May cause respiratory irritation (16.7% of reports)
H351Suspected of causing cancer (16.7% of reports)

Precautionary statements: P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

Storage

Storage: Store at 20 °C to 25 °C (68 °F to 77 °F); excursions permitted to 15 °C to 30 °C (59 °F to 86 °F).[1]
Keep container tightly closed in a dry and well-ventilated place. (pioglitazone hydrochloride)[1]
Precautions FOR "carcinogens": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... Expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... Should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... Should be contiguous to storage area. (chemical Carcinogens)[1]

Safety data sheets on the supplier’s page: Enamine, Key Organics/BIONET, DempoChem.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
[2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[3]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
[6]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.