ChemicalBook--->CAS DataBase List--->105355-27-9

105355-27-9

105355-27-9 Structure

105355-27-9 Structure
IdentificationBack 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 PropertiesBack 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 DataBack Directory
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Carc. 2
Hazard InformationBack 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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