ChemicalBook > CAS DataBase List > Pioglitazone hydrochloride

Pioglitazone hydrochloride

Product Name
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;Pioglitazone Hydro...
CBNumber
CB0411844
Molecular Formula
C19H21ClN2O3S
Formula Weight
392.9
MOL File
112529-15-4.mol
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Pioglitazone hydrochloride Property

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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/38-36
Safety Statements 
22-24/25-26
WGK Germany 
3
HazardClass 
IRRITANT
HS Code 
29341000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

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

Raw materials

Preparation Products

Pioglitazone
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View Lastest Price from Pioglitazone hydrochloride manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Pioglitazone hydrochloride 112529-15-4
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-13
Hebei Chuanghai Biotechnology Co,.LTD
Product
Pioglitazone 112529-15-4
Price
US $19.10/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 ton
Release date
2024-08-20
Wuhan Boyuan Import & Export Co., LTD
Product
Pioglitazone hydrochloride 112529-15-4
Price
US $9.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000tons
Release date
2023-05-17

112529-15-4, Pioglitazone hydrochlorideRelated Search:

Rosiglitazone Liraglutide Repaglinide Melatonine WY-14643 MK-2206 2HCl HS-173 Vorinostat 17-AAG 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide Hydroxypioglitazone Pioglitazone Sulfonic Acid IMpurity 2-[2-(4-BroMophenoxy)ethyl]-5-ethylpyridine a-[(Aminocarbonyl)thio]-4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzenepropanoic Acid Ethyl Ester Hydroxy Pioglitazone (M-II) (Mixture of Diastereomers) 4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzyaldehyde Pioglitazone Impurity 5-{4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl}-2-imino-4-thiazolidinone

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  • $350/50G,99%,IN STOCK
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  • 112529-15-4
  • 12529-15-4
  • C19H20N2O3SHCl
  • C19H20N2O3SxHCl
  • C20H21N2O3S
  • C19H21N2O3ClS
  • C19H20N2O3SClH
  • C19H21ClN2O3S