Pioglitazone

Base Information

• Chemical Name: Pioglitazone
• CAS No.: 111025-46-8
• Deprecated CAS: 105355-27-9,198077-89-3
• Molecular Formula: C₁₉H₂₀N₂O₃S
• Molecular Weight: 356.445
• European Community (EC) Number: 601-029-7,921-004-7
• NSC Number: 758876
• UNII: X4OV71U42S
• DSSTox Substance ID: DTXSID3037129
• Nikkaji Number: J277.717G
• Wikipedia: Pioglitazone
• Wikidata: Q417765
• NCI Thesaurus Code: C71633
• RXCUI: 33738
• Pharos Ligand ID: 83H7MQCQ2W8Z
• Metabolomics Workbench ID: 43356
• ChEMBL ID: CHEMBL595
• Mol file: 111025-46-8.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

Chemical Property:

• Appearance/Colour: Colorless needle crystal
• Vapor Pressure: 3.03E-13mmHg at 25°C
• Melting Point: 183-184 °C
• Boiling Point: 575.4 °C at 760 mmHg
• PKA: 6.35±0.50(Predicted)
• Flash Point: 301.8 °C
• PSA: 93.59000
• Density: 1.26 g/cm³
• LogP: 4.29040
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly, Heated)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 356.11946368
• Heavy Atom Count: 25
• Complexity: 466

Purity/Quality:

99.9% ^*data from raw suppliers

Pioglitazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Hypoglycemic Agents
• Canonical SMILES: CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3
• Recent ClinicalTrials: Targeting Residual Activity By Precision, Biomarker-Guided Combination Therapies of Multiple Sclerosis (TRAP-MS)
• Recent EU Clinical Trials: Towards a treatment for accelerated maturation in girls testing spiomet in a randomised placebo controlled, multicentre study.
• Recent NIPH Clinical Trials: Drug-drug interactions study of TAS-115 in patients with solid tumors
• Description: Pioglitazone is an agonist of the peroxisome proliferator-activated receptor γ (PPARγ; EC50 = ~500-600 nM for both human and murine PPARγ). It is selective for PPARγ over PPARα, exhibiting low level activation of PPARα at 1 μM and 5.4-fold activation at a concentration of 10 μM. Pioglitazone inhibits pyruvate oxidation and glucose production in hepatocytes when used at a concentration of 10 μM. In vivo, pioglitazone (0.3-3 mg/kg per day) reduces hyperglycemia, hyperlipidemia, and hyperinsulinemia in a dose-dependent manner in male Wistar fatty rats. It reduces the number of lesions in a transgenic rat adenocarcinoma of prostate (TRAP) model. Pioglitazone (2.5 mg/kg) also decreases production of neuroinflammatory cytokines and reduces immobility in the forced swim and tail suspension tests in a mouse model of chronic mild stress, indicating antidepressant-like activity that can be reversed by the PPARγ antagonist GW9662 .
• Uses: antihyperlipidemic, HMGCoA reductase inhibitor Pioglitazone shows antidiabetic activity in patients with type 2 diabetes mellitus.
• Indications: Pioglitazone is approved for use as monotherapy and in conjunction with metformin, sulfonylureas, and insulin. It is taken once a day with or without food. Though pioglitazone may also cause a small increase in low-density lipoprotein concentrations, there is usually a modest decrease in triglyceride levels, but it unclear whether this has any clinical significance or persists in the long term.
• Therapeutic Function: Antidiabetic

Technology Process of Pioglitazone

There total 59 articles about Pioglitazone 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: 100.0%

5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzylidene}-2,4-thiazolidinedione (136401-69-9) → Pioglitazone (105355-27-9,111025-46-8)

Guidance literature:

With hydrogen; polymer incarcerated palladium; In tetrahydrofuran; at 20 ℃; for 24h; under 760 Torr;

DOI:10.1021/jo0358527

Reference yield: 90.0%

5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2-imino-4-thiazolidinone (105355-26-8) → Pioglitazone (105355-27-9,111025-46-8)

Guidance literature:

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

Reference yield: 88.0%

(E)-5-<4-<2-(5-Ethyl-2-pyridyl)ethoxy>benzylidene>-2,4-thiazolidinedione (136401-70-2) → Pioglitazone (105355-27-9,111025-46-8)

Guidance literature:

With sodium tetrahydroborate; butane-2,3-dione-bis-methylimine; sodium hydroxide; cobaltous chloride hexahydrate; In polyethylene glycol-400 (PEG-400); water; N,N-dimethyl-formamide; at 0 - 15 ℃;

upstream raw materials:

5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2-imino-4-thiazolidinone

5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzylidene}-2,4-thiazolidinedione

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

4-fluorobenzonitrile

Downstream raw materials:

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

(5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione L-tartrate

(5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione tosylate

(5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione hydrochloride

Refernces

• 1、 Mohanty, Sandeep,Reddy. G, Sandeep,Karmakar, Arun Chandra. "Phosphoryl chloride mediated synthesis of 5-arylidene-2,4- thiazolidinediones derivatives via aromatic bisulfite adducts". . p. 197 - 202. Retrieved 2014/05/20.
• 2、 Altun, Oezlen,Kuecuektepe, Caner,Yoeruek, Ozan,Feyizoglu, Adilhan. "Practical synthesis of pioglitazone: Ligand substitution reaction with oxido vanadium(IV) and biological activity". . p. 221 - 225. Retrieved 2013/04/10.