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Pioglitazone hydrochloride

CAS No.
112529-15-4
Chemical Name:
Pioglitazone hydrochloride
Synonyms
PIOGLITAZONE HCL;ACTOS;Piog;PiogL;AD-4833;U-72107E;U-72107A;itazone HydrochL;$350/50G,99%,IN STOCK;Effects of pioglitazone
CBNumber:
CB0411844
Molecular Formula:
C19H21ClN2O3S
Molecular Weight:
392.9
MDL Number:
MFCD04975446
MOL File:
112529-15-4.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

Pioglitazone hydrochloride Properties

Melting point 193-194°C
RTECS XJ5813440
storage temp. 2-8°C
solubility DMSO: ≥10mg/mL
form powder
color white to off-white
Water Solubility Soluble in water (<1 mg/ml at 25°C), DMF, methanol, ethanol (4 mg/ml at 25°C), and DMSO (79 mg/ml at 25°C).
Merck 14,7452
BCS Class 2
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKey GHUUBYQTCDQWRA-UHFFFAOYSA-N
CAS DataBase Reference 112529-15-4(CAS DataBase Reference)
NCI Dictionary of Cancer Terms Actos
FDA UNII JQT35NPK6C
NCI Drug Dictionary Actos

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H319
Precautionary statements  P264-P280i-P305+P351+P338-P337+P313
Hazard Codes  Xi
Risk Statements  36/38-36
Safety Statements  22-24/25-26
WGK Germany  3
HazardClass  IRRITANT
HS Code  29341000
NFPA 704
1
2 0

Pioglitazone hydrochloride price More Price(56)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich E6910 Pioglitazone hydrochloride ≥98% (HPLC) 112529-15-4 10mg $79.5 2024-03-01 Buy
Sigma-Aldrich 1539905 Pioglitazone hydrochloride United States Pharmacopeia (USP) Reference Standard 112529-15-4 100mg $436 2024-03-01 Buy
TCI Chemical P1901 Pioglitazone Hydrochloride >98.0%(HPLC)(N) 112529-15-4 5g $183 2024-03-01 Buy
TCI Chemical P1901 Pioglitazone Hydrochloride >98.0%(HPLC)(N) 112529-15-4 25g $549 2024-03-01 Buy
Alfa Aesar H60507 Pioglitazone hydrochloride, 98% 112529-15-4 250mg $50.61 2023-01-06 Buy
Product number Packaging Price Buy
E6910 10mg $79.5 Buy
1539905 100mg $436 Buy
P1901 5g $183 Buy
P1901 25g $549 Buy
H60507 250mg $50.61 Buy

Pioglitazone hydrochloride Chemical Properties,Uses,Production

Description

Pioglitazone is a new orally active thiazolidinedione (TZD) launched in the US for the treatment of non-insulin dependent diabetes mellitus (NIDDM). It can be synthesized in 4 steps, the last one transforming an alphabromoester into thiazolidine with thiourea. As with other representatives in this class, it potently activates the nuclear receptor peroxisome proliferator-activated receptor gamma which is believed to be involved in the regulation of insulin resistance and adipogenesis. In several obese and obese diabetic animal models, treatment with Pioglitazone resulted in reductions in plasma glucose and serum lipids. In clinical studies, Pioglitazone at a once daily oral dose of 15-45 mg, as monotherapy or in combination with non-TZDs or insulin, was shown to significantly improve glycemic control in type-2 diabetes and demonstrated a beneficial effect on insulin resistance and other clinically relevant parameters as plasma levels of triglycerides or HDL-cholesterol. Pioglitazone is reported to be safe and well tolerated and is said to have a lower occurrence of hepatic toxicity as well as a low probability for drug interaction.

Chemical Properties

Colourless Prisms

Originator

Takeda (Japan)

Uses

Pioglitazone Hydrochloride is used as an antidiabetic.

Uses

Pioglitazone hydrochloride is a euglycemic agent,used as an antidiabetic.

Definition

ChEBI: Pioglitazone hydrochloride is an aromatic ether.

Manufacturing Process

To a solution of 2-(5-ethyl-2-pyridyl)ethanol (53.0 g) and 4-fluoronitrobenzene (47.0 g) in DMF (500 ml) was added portionwise under ice-cooling 60% sodium hydride in oil (16.0 g). The mixture was stirred under ice-cooling for one hour, then at room temperature for 30 min, poured into water and extracted with ether. The ether layer was washed with water and dried (MgSO4). The solvent was evaporated off to give 4-[2-(5-ethyl-2pyridyl)ethoxy]nitrobenzene as crystals (62.0 g, 62.9%). Recrystallization from ether-hexane gave colorless prisms, melting point 53°-54°C.
A solution of 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene (60.0 g) in methanol (500 ml) was hydrogenated at room temperature under one atmospheric pressure in the presence of 10% Pd-C (50% wet, 6.0 g). The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residual oil was dissolved in acetone (500 ml)methanol (200 ml). To the solution was added a 47% HBr aqueous solution (152 g). The mixture was cooled, to which was added dropwise a solution of NaNO2 (17.3 g) in water (30 ml) at a temperature not higher than 5°C. The whole mixture was stirred at 5°C for 20 min, then methyl acrylate (112 g) was added thereto and the temperature was raised to 38°C. Cuprous oxide (2.0 g) was added to the mixture in small portions with vigorous stirring. The reaction mixture was stirred until nitrogen gas evolution ceased, and was concentrated under reduced pressure. The concentrate was made alkaline with concentrated aqueous ammonia, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4) The solvent was evaporated off to leave methyl 2-bromo-3-{4-[2-(5-ethyl-2pyridyl)ethoxy]phenyl}propionate as a crude oil (74.09 g, 85.7%).
A mixture of the crude oil of methyl 2-bromo-3-{4-[2-(5-ethyl-2pyridyl)ethoxy]phenyl}propionate (73.0 g) thiourea (14.2 g), sodium acetate (15.3 g) and ethanol (500 ml) was stirred for 3 hours under reflux. The reaction mixture was concentrated under reduced pressure, and the concentrate was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, to which were added water (200 ml) and ether (100 ml). The whole mixture was stirred for 10 min to yield 5-{4-[2-(5-ethyl-2pyridyl)ethoxy]benzyl}-2-imino-4-thiazolidinone as crystals (0.3 g, 523.0%). Recrystallization from methanol gave colorless prisms, melting point 187°188°C, dec.
A solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2-imino-4thiazolidinone (23.5 g) in 2 N HCl (200 ml) was refluxed for 6 hours. The solvent was evaporated off under reduced pressure, and the residue was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The crystals (23.5 g, 97.5%) which precipitated were collected by filtrationand recrystallized from DMF-H2O to give 5-{4-[2-(5-ethyl-2pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione as colorless needles (20.5 g, 86.9%), melting point 183°-184°C.
In practice it is usually used as hydrochloride salt.

brand name

Actos (Takeda).

Therapeutic Function

Antidiabetic

General Description

Pioglitazone hydrochloride is an oral antidiabetic agent used in the treatment of type 2 diabetes mellitus (also known as non-insulin-dependent diabetes mellitus (NIDDM) or adult-onset diabetes.

Biochem/physiol Actions

Selective PPARγ agonist

storage

room temperature (desiccate)

References

1) Merck 14:7452 2) Sakamoto et al. (2000), Activation of human peroxisome proliferator-activated receptor (PPAR) subtypes by pioglitazone; Biochem. Biophys. Res. Commun., 278 704 3) Wilson et al. (2000), The PPARs: From Orphan Receptors to Drug Discovery; J. Med. Chem., 43 527 4) Shannon et al. (2017), Pioglitazone Inhibits Mitochondrial Pyruvate Metabolism and Glucose Production in Hepatocytes; FEBS J., 284 451 5) Zhao et al. (2016), The Antidepressant-Like Effects of Pioglitazone in a Chronic Mild Stress Mouse Model Are Associated With PPARγ-Mediated Alteration of Microglial Activation Phenotypes; Neuroinflamm., 13 259

Pioglitazone hydrochloride Preparation Products And Raw materials

Global( 673)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Mojin Biotechnology Co., Ltd
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+86-15175982296 15175982296; Mike@whby-chem.com China 981 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293 sales@sdzschem.com China 2931 58

View Lastest Price from Pioglitazone hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Pioglitazone hydrochloride pictures 2024-01-08 Pioglitazone hydrochloride
112529-15-4
US $9.00 / KG 1KG 99% 50000tons Wuhan Boyuan Import & Export Co., LTD
pioglitazone hydrochloride	 pictures 2023-11-21 pioglitazone hydrochloride
112529-15-4
US $1.00 / g 1000g 99% 20ton/month Wuhan Aoliqisi New Material Technology Co., Ltd.
Pioglitazone hydrochloride pictures 2023-09-25 Pioglitazone hydrochloride
112529-15-4
US $65.00-60.00 / KG 1KG 99% 10 Ton Anhui Yisheng Technology Co., LTD

Pioglitazone hydrochloride Spectrum

5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzylidine]-2,4-thiazolidinedionehydrochloride AD-4833 pioglitazone hydrochioride Pioditazone hydrochloride PIODLITAZONE HYDROCHLORIC 5-{4-[2-(5-ETHYL-PYRIDIN-2-YL)-ETHOXY]-BENZYL}-THIAZOLIDINE-2,4-DIONE HCL 5-{4-[2-(5-Ethyl-pyridin-2-yl)-ethoxy]-benzyl}- 5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione hydrochloride 5-[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzyl]thiazolidine-2,4-dione hydrochloride Pioglitazone Hydrochloride (50 mg) (5R)-5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}Methyl)-1,3-thiazolidine-2,4-dione Effects of pioglitazone 5-[4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl]-2,4-thiazolidinedione Hydrochloride [5-[[4-[2-(5-ETHYL-PYRIDIN-2-YL)ETHOXY]PHENYL]METHYL]-2,4-] THIAZOLIDINEDIONE HCL (R)-5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione hydrochloride 5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione monohydrochloride Pioglitazone for system suitability 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione,hydrochloride (1:1) U-72107E Pioglitazone hydrochloride, >=99% thiazolidinedione hydrochloride 5-[4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl]thiazolidine-2,4-dione hydrochloride U-72107A 5-((4-(2-(5-ETHYL-2-PYRIDINYL)ETHOXY)PHENYL)METHYL)-2,4-THIAZOLIDINEDIONE, HCL [5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-] thiazolidinedione hydrochloride PIOGLITAZONE HYDROCHLORIDE (RS)-5-(4-[2-(5-Ethylpyridin-2-yl)ethoxy]benzyl)thiazolidine-2,4-dione hydrochloride Pioglitazone hydrochloride, 99%, a receptor-gamma (PPARgamma) agonist (+-5-[[4-[2-(5-ETHYL-2-PYRIDINYL)ETHOXY] PHENYL]METHYL]-2 4-] THIAZOLIDINEDIONE H YDROCHLORIDE(PIOGLITAZONE HCL) Pioglitazone hydrochloride, 99%, receptor-gamma (PPARgamma) agonist $350/50G,99%,IN STOCK Pioglitazone hydrochloride SALT Pioglitazone for system suitability CRS Pioglitazone hydrochloride CRS PioglitazoneHydrochloride> Pioglitazone Hydrochloride RS itazone HydrochL Piog Pioglitazone hydrochloride Solution in Methanol, 100μg/mL PiogL Pioglitazone hydrochloride USP/EP/BP Pioglitazone hydrochloride5-[[4-[2-(5-Ethyl-2-pyridinyl)-ethoxy]phenyl]Methyl]-2,4-thiazolidinedionehydrochloride Pioglitazone HydrochlorideQ: What is Pioglitazone Hydrochloride Q: What is the CAS Number of Pioglitazone Hydrochloride Q: What is the storage condition of Pioglitazone Hydrochloride Q: What are the applications of Pioglitazone Hydrochloride Pioglitazone hydrochloride, 98%, Pioglitazone Hydrochloride (1539905) ACTOS PIOGLITAZONE HCL Pioglitazone hydrochloride (RS)-5-(4-[2-(5-Ethylpyridin-2-yl)ethoxy]benzyl)thiazolidine-2,4- dione hydrochloride 112529-15-4 12529-15-4 C19H20N2O3SHCl C19H20N2O3SxHCl C20H21N2O3S C19H21N2O3ClS C19H20N2O3SClH C19H21ClN2O3S Cardiovascular Series API