Pioglitazone hydrochloride

Base Information

• Chemical Name: Pioglitazone hydrochloride
• CAS No.: 112529-15-4
• Deprecated CAS: 127676-30-6
• Molecular Formula: C19H21ClN2O3S
• Molecular Weight: 392.906
• Hs Code.: 29341000
• European Community (EC) Number: 629-731-9
• UNII: JQT35NPK6C
• DSSTox Substance ID: DTXSID3044203
• Wikidata: Q27281642
• NCI Thesaurus Code: C29367
• RXCUI: 259319
• ChEMBL ID: CHEMBL1715
• Mol file: 112529-15-4.mol

Synonyms:5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione;Actos;AD 4833;AD-4833;AD4833;pioglitazone;pioglitazone hydrochloride;U 72107A;U-72107A;U72,107A;U72107A

Chemical Property of Pioglitazone hydrochloride

Chemical Property:

• Appearance/Colour: white crystals or crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 193-194 ºC
• Refractive Index: 1.64
• Boiling Point: 575.4 ºC at 760 mmHg
• Flash Point: 301.8 ºC
• PSA: 93.59000
• Density: 1.26 g/cm³
• LogP: 4.29040
• Storage Temp.: Desiccate at RT
• Solubility.: DMSO: ≥10mg/mL
• 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).
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 392.0961414
• Heavy Atom Count: 26
• Complexity: 466

Purity/Quality:

98%min ^*data from raw suppliers

Pioglitazone hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38-36
• Safety Statements: 22-24/25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3.Cl
• Recent ClinicalTrials: Pioglitazone Hydrochloride in Preventing Head and Neck Cancer in Patients With Oral Leukoplakia
• Recent EU Clinical Trials: Control strategies and pharmacogenetic study for the personalized treatment of fatty liver associated with metabolic dysfunction in patients with prediabetes.
• Recent NIPH Clinical Trials: he efficacy of alogliptin to gastrin and glycemic control in patients with type 2 diabetes under treatment with gastric secretion inhibitor and gastroprotective agents
• 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.
• Uses: euglycemic agent Pioglitazone Hydrochloride is used as an antidiabetic. Pioglitazone hydrochloride is a euglycemic agent,used as an antidiabetic.
• Therapeutic Function: Antidiabetic

Technology Process of Pioglitazone hydrochloride

There total 34 articles about Pioglitazone hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

Pioglitazone (105355-27-9,111025-46-8) → 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride (112529-15-4)

Guidance literature:

With hydrogenchloride; In ethanol; at 10 - 65 ℃; for 4.25h; Product distribution / selectivity;

Reference yield:

2-bromo-3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}propionic acid (674798-32-4) + thiourea (17356-08-0) → 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride (112529-15-4)

Guidance literature:

2-bromo-3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}propionic acid; thiourea; With sodium acetate; In ethanol; for 3h; Heating / reflux;

With hydrogenchloride; In ethanol; water; for 18h; Heating / reflux;

With ammonia; In ethanol; water; at 20 ℃;

Reference yield:

5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2-imino-4-thiazolidinone (105355-26-8) → 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride (112529-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2N HCl / 6 h / Heating

2: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature

With hydrogenchloride;

upstream raw materials:

Pioglitazone

5-ethyl-2-(2-hydroxyethyl)pyridine

4-[2-(5-ethylpyridin-2-yl)ethoxy]aniline

4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene

Downstream raw materials:

rac-5-({p-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl}methyl)-(5-²H)-1,3-thiazolidine-2,4-dione

rac-2-(2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxy}ethyl)-5-ethylpyridine-1-oxide

3-(4-(2-(5-ethylpyridine-2yl)ethoxy)phenyl)-2-mercaptopropanoic acid

2-(1-carboxy-2-{4-[2-(5-ethylpyridine-2yl)-ethoxy]phenyl}-ethyldisulfanyl)-3-{4-[2-(5-ethylpyridine-2yl)-ethoxy]phenyl}propanoic acid

Refernces

• 1、 -. "5-(4-HYDROXYBENZYL)THIAZOLIDINE-2,4-DIONE AS INTERMEDIATE FOR SYNTHESIS OF THIAZOLIDINEDIONE BASED COMPOUNDS AND PROCESS FOR PREPARING THE SAME". Page/Page column 15; 22-23. . Retrieved 2009/12/28.
• 2、 Madivada, Lokeswara Rao,Anumala, Raghupathi Reddy,Gilla, Goverdhan,Alla, Sampath,Charagondla, Kavitha,Kagga, Mukkanti,Bhattacharya, Apurba,Bandichhor, Rakeshwar. "An improved process for pioglitazone and its pharmaceutically acceptable salt". experimental part. p. 1190 - 1194. Retrieved 2010/04/22.