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112529-15-4 molecular structure
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5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride

ChemBase ID: 44463
Molecular Formular: C19H21ClN2O3S
Molecular Mass: 392.89964
Monoisotopic Mass: 392.09614122
SMILES and InChIs

SMILES:
C(c1ccc(cc1)OCCc1ncc(cc1)CC)C1SC(=O)NC1=O.Cl
Canonical SMILES:
CCc1ccc(nc1)CCOc1ccc(cc1)CC1SC(=O)NC1=O.Cl
InChI:
InChI=1S/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
InChIKey:
GHUUBYQTCDQWRA-UHFFFAOYSA-N

Cite this record

CBID:44463 http://www.chembase.cn/molecule-44463.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride
IUPAC Traditional name
pioglitazone hydrochloride
5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride
Synonyms
Pioglitazone hydrochloride
Actos
5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione hydrochloride
5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride
Glustin
Zactos
5-(4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl)thiazolidine-2,4-dione hydrochloride
5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione monohydrochloride
Pioglitazone hydrochloride
5-[[4-[2-(5-Ethyl-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione Hydrochloride
AD-4833
U-72107A
CAS Number
112529-15-4
111025-46-8
MDL Number
MFCD04975446
PubChem SID
162049226
PubChem CID
60560

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 7.6181993  H Acceptors
H Donor LogD (pH = 5.5) 3.212589 
LogD (pH = 7.4) 3.361462  Log P 3.461536 
Molar Refractivity 97.3908 cm3 Polarizability 37.941406 Å3
Polar Surface Area 68.29 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
DMSO: ≥10 mg/mL expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
white to off-white powder expand Show data source
Melting Point
193-194°C expand Show data source
Hydrophobicity(logP)
3.533 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
XJ5813440 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36 expand Show data source
Safety Statements
26 expand Show data source
26-60 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H319 expand Show data source
GHS Precautionary statements
P280-P264-P305+P351+P338-P337+P313 expand Show data source
P305 + P351 + P338 expand Show data source
Storage Temperature
room temp expand Show data source
Mechanism of Action
Nuclear receptor peroxisome proliferator activated receptor (PPAR) agonist expand Show data source
Purity
>99% expand Show data source
≥98% (HPLC) expand Show data source
95% expand Show data source
98% expand Show data source
Salt Data
HCl expand Show data source
hydrochloride expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antidiabetic expand Show data source
Antihyperlipidaemic agent expand Show data source
Hypoglycemic expand Show data source
Empirical Formula (Hill Notation)
C19H20N2O3S · HCl expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S2046 external link
Research Area: Cancer
Biological Activity:
Sigma Aldrich - E6910 external link
Biochem/physiol Actions
Pioglitazone hydrochloride is a PPARγ agonist and thiazolidinedione (TZD) anti-diabetic. Pioglitazone is a selective agonist of the nuclear receptor peroxisome proliferator-activated receptor γ (PPAR-γ) and to a lesser extent PPAR-α.
Toronto Research Chemicals - P471000 external link
Used as an antidiabetic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Hofmann, C., et al.: Endocrinology, 129, 1915(1991)
  • • Kobayashi, M., et al.: Diabetes, 41, 476 (1991)
  • • Kawaamori, R., et al.,: Diabetes Res. Clin. Pract., 41, 35 (1998)
  • • 1. Gillies PS, Dunn CJ (August 2000). Pioglitazone. Drugs 60 (2): 333?3; discussion 344?.
  • • 2. Smith U (September 2001). Pioglitazone: mechanism of action. Int J Clin Pract Suppl (121): 13?.
  • • 3. Colca JR, McDonald WG, Waldon DJ, Leone JW, Lull JM, Bannow CA, Lund ET, Mathews WR (2004).
  • • Identification of a novel mitochondrial protein (mitoNEET) cross-linked specifically by a thiazolidinedione photoprobe. Am. J. Physiol. Endocrinol. Metab. 286 (2): E252?0.
  • • 4. Paddock ML, Wiley SE, Axelrod HL, Cohen AE, Roy M, Abresch EC, Capraro D, Murphy AN et al. (2007).
  • • MitoNEET is a uniquely folded 2Fe 2S outer mitochondrial membrane protein stabilized by pioglitazone. Proc. Natl. Acad. Sci. U.S.A. 104 (36): 14342?.
  • • 5. Belfort R, Harrison SA, Brown K, Darland C, Finch J, Hardies J, Balas B, Gastaldelli A et al. (2006). A placebo-controlled trial of pioglitazone in subjects with nonalcoholic steatohepatitis.
  • • N. Engl. J. Med. 355 (22): 2297?07.
  • • 6. Lincoff AM, Wolski K, Nicholls SJ, Nissen SE (2007). Pioglitazone and risk of cardiovascular events in patients with type 2 diabetes mellitus: a meta-analysis of randomized trials.
  • • JAMA 298 (10): 1180?.
  • • 7. Nissen SE, Nicholls SJ, Wolski K (2008). Comparison of pioglitazone vs glimepiride on progression of coronary atherosclerosis in patients with type 2 diabetes. JAMA 299 (13): 1561.
  • • 8. R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1271-1272.
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PATENTS

PATENTS

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INTERNET

INTERNET

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