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5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride
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ChemBase ID:
44463
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Molecular Formular:
C19H21ClN2O3S
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Molecular Mass:
392.89964
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Monoisotopic Mass:
392.09614122
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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
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Cite this record
CBID:44463 http://www.chembase.cn/molecule-44463.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride
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IUPAC Traditional name
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pioglitazone hydrochloride
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5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride
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Synonyms
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Pioglitazone hydrochloride
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Actos
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5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione hydrochloride
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5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride
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Glustin
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Zactos
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5-(4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl)thiazolidine-2,4-dione hydrochloride
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5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione monohydrochloride
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Pioglitazone hydrochloride
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5-[[4-[2-(5-Ethyl-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione Hydrochloride
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AD-4833
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U-72107A
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CAS Number
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MDL Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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7.6181993
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H Acceptors
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4
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H Donor
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1
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LogD (pH = 5.5)
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3.212589
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LogD (pH = 7.4)
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3.361462
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Log P
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3.461536
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Molar Refractivity
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97.3908 cm3
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Polarizability
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37.941406 Å3
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Polar Surface Area
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68.29 Å2
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Rotatable Bonds
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7
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Lipinski's Rule of Five
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true
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DETAILS
DETAILS
Selleck Chemicals
Sigma Aldrich
TRC
Sigma Aldrich -
E6910
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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. |
REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google 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
PubChem Patent
Google Patent