CAS 111025-46-8|CAS 112529-15-4|pioglitazone hydrochloride|5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride|Pioglitazone hydrochloride|AD-4833|5-[[4-[2-(5...

General Information

Structure

Molecular Formula

C₁₉H₂₁ClN₂O₃S

Molecular Mass

392.89964

Exact Mass

392.09614122

Charge

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

Canonic Smiles

CCc1ccc(nc1)CCOc1ccc(cc1)CC1SC(=O)NC1=O.Cl

Isomeric Smiles

C(c1ccc(cc1)OCCc1ncc(cc1)CC)C1SC(=O)NC1=O.Cl

Calculated Properties

Provided by Enamine

CLogP

3.53

H Donor

Polar Surface Area

68.29

Rotatable Bonds

JChem

Polar Surface Area

68.29

H Donor

H Acceptors

Rotatable Bonds

Lipinski's Rule of Five

true

Log P

3.40

LogD (pH = 5.5)

3.21

LogD (pH = 7.4)

3.23

Acid pKa

7.32

Molar Refractivity

97.39

Polarizability

37.61

LOG S

-4.71

Data Source

Names and Identifiers

IUPAC Traditional name

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

IUPAC name

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

Synonyms

Pioglitazone hydrochlorideAD-48335-[[4-[2-(5-Ethyl-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione HydrochlorideActosZactosGlustin5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione monohydrochlorideU-72107APioglitazone hydrochloride5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride5-(4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl)thiazolidine-2,4-dione hydrochloride5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione hydrochloride

API Name

Pioglitazone hydrochloride

Names and Identifiers

Registration numbers

CAS Number

111025-46-8112529-15-4

MDL Number

PubChem CID

PubChem SID

DrugBank ID

Registration numbers

Properties

Pharmacology Properties

Mechanism of Action

Nuclear receptor peroxisome proliferator activated receptor (PPAR) agonist

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S2046

Research Area: Cancer
Biological Activity:

Sigma Aldrich

E6910

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.

TRC

P471000

Used as an antidiabetic.

Molecule Details

References

PubChem Literature

From Data Sources

• Kobayashi, M., et al.: Diabetes, 41, 476 (1991)

• Hofmann, C., et al.: Endocrinology, 129, 1915(1991)

• Kawaamori, R., et al.,: Diabetes Res. Clin. Pract., 41, 35 (1998)

• 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.

• MitoNEET is a uniquely folded 2Fe 2S outer mitochondrial membrane protein stabilized by pioglitazone. Proc. Natl. Acad. Sci. U.S.A. 104 (36): 14342?.

• N. Engl. J. Med. 355 (22): 2297?07.

• JAMA 298 (10): 1180?.

• 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.

• 4. Paddock ML, Wiley SE, Axelrod HL, Cohen AE, Roy M, Abresch EC, Capraro D, Murphy AN et al. (2007).

• 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.

• 1. Gillies PS, Dunn CJ (August 2000). Pioglitazone. Drugs 60 (2): 333?3; discussion 344?.

• 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.

• 2. Smith U (September 2001). Pioglitazone: mechanism of action. Int J Clin Pract Suppl (121): 13?.

• 8. R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1271-1272.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

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

IUPAC name

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

Synonyms

API Name

Pioglitazone hydrochloride

Registration numbers

CAS Number

111025-46-8112529-15-4

MDL Number

PubChem CID

PubChem SID

DrugBank ID

Molecule Details

S2046

Research Area: Cancer
Biological Activity:

Sigma Aldrich

E6910

TRC

P471000

Used as an antidiabetic.

References

PubChem Literature

From Data Sources

• Kobayashi, M., et al.: Diabetes, 41, 476 (1991)

• Hofmann, C., et al.: Endocrinology, 129, 1915(1991)

• Kawaamori, R., et al.,: Diabetes Res. Clin. Pract., 41, 35 (1998)

• 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.

• MitoNEET is a uniquely folded 2Fe 2S outer mitochondrial membrane protein stabilized by pioglitazone. Proc. Natl. Acad. Sci. U.S.A. 104 (36): 14342?.

• N. Engl. J. Med. 355 (22): 2297?07.

• JAMA 298 (10): 1180?.

• 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.

• 4. Paddock ML, Wiley SE, Axelrod HL, Cohen AE, Roy M, Abresch EC, Capraro D, Murphy AN et al. (2007).

• 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.

• 1. Gillies PS, Dunn CJ (August 2000). Pioglitazone. Drugs 60 (2): 333?3; discussion 344?.

• 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.

• 2. Smith U (September 2001). Pioglitazone: mechanism of action. Int J Clin Pract Suppl (121): 13?.

• 8. R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1271-1272.

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Mechanism of Action

Nuclear receptor peroxisome proliferator activated receptor (PPAR) agonist

Molecule

ID:44463