105355-27-9

Basic information

• Product Name: Pioglitazone
• Synonyms: 5-[[4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl]methyl]thiazolidine-2,4-dione;Pioglitazone;5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}Methyl)-1,3-thiazolidine-2,4-dione hydrochloride
• CAS NO: 105355-27-9
• Molecular Formula: C₁₉H₂₀N₂O₃S
• Molecular Weight: 356.44
• Mol File: 105355-27-9.mol
• Article Data: 45

Chemical Properties

• Boiling Point: 575.4 °C at 760 mmHg
• Flash Point: 301.8 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 3.03E-13mmHg at 25°C
• CAS DataBase Reference: Pioglitazone(CAS DataBase Reference)
• NIST Chemistry Reference: Pioglitazone(105355-27-9)
• EPA Substance Registry System: Pioglitazone(105355-27-9)

Safety Data

• Hazardous Substances Data: 105355-27-9(Hazardous Substances Data)

Usage

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%).

InChI:InChI=1/C19H20N2O3S.ClH/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);1H

Upstream product

• 19842-08-1 2-bromo-5-ethylpyridine 
• 81675-78-7 4-(vinyloxy)benzaldehyde 
• 646519-94-0 5-{4-[2-chloro-2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione 
• 646519-92-8 5-{4-[2-(5-ethylpyridin-2-yl)-2-tosylethoxy]benzylidene}-2,4-thiazolidene dione 
• 646519-90-6 5-{4-[2-(5-ethylpyridin-2-yl)-2-mesylethoxy]benzylidene}-2,4-thiazolidene dione 
• 105355-25-7 methyl 2-bromo-3-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]phenyl}propionate 
• 17356-08-0 thiourea 
• 74772-78-4 5-(4-hydroxybenzyl)-2,4-thiazolidinedione 
• 144809-27-8 toluene-4-sulfonic acid 2-(5-ethylpyridin-2-yl)ethyl ester 
• 136401-70-2 (E)-5-<4-<2-(5-Ethyl-2-pyridyl)ethoxy>benzylidene>-2,4-thiazolidinedione 
• 914249-67-5 pioglitazone imino ether 
• 646519-89-3 5-{4-[2-chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-2,4-thiazolidene dione hydrochloride 
• 646519-88-2 5-{4-[2-chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-2,4-thiazolidene dione 
• 144809-28-9 5-{4-[2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione 

Downstream Products

• 145350-09-0 rac-2-(2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxy}ethyl)-5-ethylpyridine-1-oxide 
• 847440-44-2 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione phosphoric acid salt 
• 952188-00-0 5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzyl}-3-[2-(5-ethyl-pyridin-2-yl)ethyl]-1,3-thiazolidine-2,4-dione 
• 16106-44-8 potassium tosylate 
• 959687-65-1 (R)-5-({p-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione 
• 1263978-84-2 (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione L-tartrate 
• 1263978-86-4 (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione tosylate 
• 1207681-45-5 (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione hydrochloride 
• 1207681-40-0 (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione trifluoroacetate 
• 1207730-80-0 (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione (-)-O,O'-dibenzoyl-L-tartrate 
• 796038-40-9 pioglitazone sulfate 
• 146062-49-9 rac-5-({p-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione 
• 101931-00-4 5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione 
• 112529-15-4 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride 

Relevant articles and documents

Practical synthesis of pioglitazone: Ligand substitution reaction with oxido vanadium(IV) and biological activity

The authors performed two types of experiments: the reduction of 5-{4-[2-(5-ethyl-2-pyridyl)etoxy]benzilidine}-2-4-thiazolidinedione to pioglitazone (5-{4-[2-(5-ethyl-2-pyridyl) etoxy]benzil}-2-4-thiazolidinedione) with magnesium/methanol and the synthesis of an oxidovanadium(IV) complex of pioglitazone in methanol under refluxing conditions. The structures of pioglitazone and its oxidovanadium(IV) complex were analyzed by using physicochemical and spectroscopic techniques. Comparisons of the spectral measurements of pioglitazone with those of its oxidovanadium(IV) ion complex are useful in determining the atoms of the ligand that are coordinated to the metal ion. In addition, antibacterial and antifungal activities of the complex were studied and the complex is screened against bacteria and fungi.

Recoverable, Reusable, Highly Active, and Sulfur-Tolerant Polymer Incarcerated Palladium for Hydrogenation

A new type of immobilized palladium, PI (polymer incarcerated) Pd (2b), from Pd(PPh3)4 and copolymer (1b) has been developed. The excellent activity of PI Pd has been demonstrated in hydrogenation of various olefins, benzyl ethers, and nitro and aromatic compounds. PI Pd is tolerant under high pressure and high temperature and can be recovered and reused several times without loss of activity even under harsh conditions. Moreover, PI Pd is highly resistant to poisoning by sulfur.

Phosphoryl chloride mediated synthesis of 5-arylidene-2,4- thiazolidinediones derivatives via aromatic bisulfite adducts

The carbon-carbon bond formation by the condensation of bisulfite adduct of aromatic aldehydes with thiazolidine-2, 4-dione to furnish 5-arylidene-2,4- thiazolidinedione's has been investigated. This novel methodology was applied to convert substituted aryl bisulfite adducts to corresponding 5-arylidene-2,4-thiazolidinedione's with POCl3 in less-polar solvents such as toluene, chlorobenzene and o-xylene. 5-(4-methoxybenzylidene) thiazolidine-2,4-dione and 5-(4-ethoxybenzylidene)thiazolidine-2,4-dione were obtained in good yields.

Glycation Cross-link Breakers to Increase Resistance to Enzymatic Degradation

The present invention relates to a method to treat a grafts, implant, scaffold, and constructs, including allografts, xenografts, autografts, and prosthetics comprising collagen, with an inhibitor of collagen cross-links and/or advanced glycation endproducts (AGE), in order to alleviate the mechanical weakness induced by the cross-links The invention also provides for kits for use in the operating theater during autograft, allograft or xenograft procedures, or for preparing allograft, xenografts or prosthetics that have not been already treated prior to packaging. The kit comprises a first agent or agents that inhibit collagen cross-links and/or advanced glycation endproducts, instructions for use, optionally a wash or rinse agent, and a device for containing the graft and first agent.