| Identification | Back Directory | [Name]
Pioglitazone | [CAS]
105355-27-9 | [Synonyms]
Pioglitazone
5-[[4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl]methyl]thiazolidine-2,4-dione
5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]thiazolidine-2,4-dione
5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}Methyl)-1,3-thiazolidine-2,4-dione hydrochloride | [Molecular Formula]
C19H20N2O3S | [MOL File]
105355-27-9.mol | [Molecular Weight]
356.44 |
| Chemical Properties | Back Directory | [form ]
solid | [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 | [SMILES]
O=C(N1)C(SC1=O)CC(C=C2)=CC=C2OCCC(N=C3)=CC=C3CC |
| Safety Data | Back Directory | [WGK Germany ]
WGK 3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Carc. 2 |
| Hazard Information | Back Directory | [Definition]
ChEBI: Pioglitazone is a member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity. It has a role as an insulin-sensitizing drug, an EC 2.7.1.33 (pantothenate kinase) inhibitor, a xenobiotic, an EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor, a ferroptosis inhibitor, a cardioprotective agent, a PPARgamma agonist, an antidepressant, a geroprotector and a hypoglycemic agent. It is a member of thiazolidinediones, an aromatic ether and a member of pyridines. | [Clinical Use]
Treatment of type 2 diabetes mellitus | [Drug interactions]
Potentially hazardous interactions with other drugs
None known | [Metabolism]
Pioglitazone undergoes extensive hepatic metabolism
by hydroxylation mainly via cytochrome P450 2C8
to form active and inactive metabolites. Three of the
six identified metabolites are active (M-II, M-III, and
M-IV). Following oral administration of radiolabelled
pioglitazone to man, recovered label was mainly in faeces
(55%) and a lesser amount in urine (45%). |
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