Pioglitazone hydrochloride
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| Category | Antidiabetic |
| Catalog number | BBF-05868 |
| CAS | 112529-15-4 |
| Molecular Weight | 392.90 |
| Molecular Formula | C19H20N2O3S.HCl |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-05868 | 250 mg | $199 | In stock |
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Pioglitazone hydrochloride, a thiazolidinedione antidiabetic drug, is a cytochrome P450 (CYP)2C8 and CYP3A4 enzymes inhibitor with Kis of 1.7, 11.8 and 32.1 μM for CYP2C8, CYP3A4 and CYP2C9, respectively. It is an agonist of the peroxisome proliferator-activated receptor γ.
Specification
| Related CAS | 111025-46-8 (free base) 1266523-09-4 (potassium salt) |
| Synonyms | 5-[[4-[2-(5-Ethyl-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione Hydrochloride; AD-4833; Actos; U-72107A; 5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione hydrochloride; NSC 758876; 2,4-Thiazolidinedione, 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-, monohydrochloride |
| Storage | Store at -20°C |
| IUPAC Name | 5-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;hydrochloride |
| Canonical SMILES | CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3.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 |
| InChI Key | GHUUBYQTCDQWRA-UHFFFAOYSA-N |
Properties
| Appearance | White to Off-white Solid |
| Application | Hypoglycemic Agents |
| Melting Point | 193-194°C |
| Solubility | Soluble in Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly) |
Reference Reading
1.Can a selective PPARγ modulator improve glycemic control in patients with type 2 diabetes with fewer side effects compared with pioglitazone?
DePaoli AM1, Higgins LS1, Henry RR2, Mantzoros C3, Dunn FL4; INT131-007 Study Group. Diabetes Care. 2014 Jul;37(7):1918-23. doi: 10.2337/dc13-2480. Epub 2014 Apr 10.
OBJECTIVE: INT131 besylate is a potent, nonthiazolidinedione, selective peroxisome proliferator-activated receptor γ (PPARγ) modulator (SPPARM) designed to improve glucose metabolism while minimizing the side effects of full PPARγ agonists. This placebo-controlled study compared the efficacy and side effects of INT131 besylate versus 45 mg pioglitazone HCl in subjects with type 2 diabetes (T2D).
2.Prodrugs of pioglitazone for extended-release (XR) injectable formulations.
Sanrame CN1, Remenar JF, Blumberg LC, Waters J, Dean RL, Dong N, Kriksciukaite K, Cao P, Almarsson O. Mol Pharm. 2014 Oct 6;11(10):3617-23. doi: 10.1021/mp500359a. Epub 2014 Sep 9.
N-Acyloxymethyl derivatives of pioglitazone (PIO) have been prepared and characterized as model candidates for extended-release injectable formulations. All PIO derivatives prepared are crystalline solids as determined by powder X-ray diffraction, and the solubility in aqueous media is below 1 μM at 37 °C. The melting points steadily increase from 55 °C, for the hexanoyloxymethyl derivative, to 85 °C, for the palmitoyloxymethyl derivative; inversely, the solubilities in ethyl oleate decrease as a function of increasing acyl chain length. The butyroyloxymethyl ester has a higher melting point and a lower solubility in ethyl oleate than expected from the trend. The (13)C solid-state NMR spectra of the PIO homologues between the hexanoyloxymethyl derivative and stearoyloxymethyl derivative suggest a common structural motif with the acyl chains exchanging between two distinct conformations, and the rate of exchange is slower for longer chain derivatives.
3.Characterizing the Dissolution Profiles of Supersaturable Salts, Cocrystals, and Solvates to Enhance In Vivo Oral Absorption.
Hisada N1, Takano R1, Takata N1, Shiraki K1, Ueto T1, Tanida S1, Kataoka M2, Yamashita S3. Eur J Pharm Biopharm. 2016 Apr 6. pii: S0939-6411(16)30128-X. doi: 10.1016/j.ejpb.2016.04.004. [Epub ahead of print]
The purposes of this study were to elucidate the type-specific characteristics of salt, cocrystal, and solvate formulations upon dissolution and precipitation, and to clarify their effect on enhancing oral absorption. Several types of solid formulations (dantrolene sodium salt [DAN-NA], pioglitazone hydrochloride salt [PIO-HCL], megestrol acetate saccharin cocrystal [MEG-SA], and an in-house compound ZR ethanolate [ZR-ETH]) that induce supersaturation of BCS class II drugs were compared to their crystalline free forms. An in vitro miniscale dissolution test in biorelevant media was used to characterize their dissolution profiles and residue forms. Both salts (DAN-NA and PIO-HCL) rapidly reached the maximum concentration within 5 minutes, whereas the cocrystal (MEG-SA) did so slowly. After the maximum concentration had been reached, the dissolved concentrations of DAN-NA, PIO-HCL, and MEG-SA decreased, but that of ZR-ETH did not. Time-dependent XRPD analysis revealed that the initial solid state of each salt dissolved within 5 minutes, whereas the cocrystal remained for more than 10 minutes, and the solvate remained for 4 hours.
4.Role of an indole-thiazolidine molecule PPAR pan-agonist and COX inhibitor on inflammation and microcirculatory damage in acute gastric lesions.
Santin JR1, Daufenback Machado I, Rodrigues SF, Teixeira S, Muscará MN, Lins Galdino S, da Rocha Pitta I, Farsky SH. PLoS One. 2013 Oct 4;8(10):e76894. doi: 10.1371/journal.pone.0076894. eCollection 2013.
The present study aimed to show the in vivo mechanisms of action of an indole-thiazolidine molecule peroxisome-proliferator activated receptor pan-agonist (PPAR pan) and cyclooxygenase (COX) inhibitor, LYSO-7, in an ethanol/HCl-induced (Et/HCl) gastric lesion model. Swiss male mice were treated with vehicle, LYSO-7 or Bezafibrate (p.o.) 1 hour before oral administration of Et/HCl (60%/0.03M). In another set of assays, animals were injected i.p. with an anti-granulocyte antibody, GW9962 or L-NG-nitroarginine methyl ester (L-NAME) before treatment. One hour after Et/HCl administration, neutrophils were quantified in the blood and bone marrow and the gastric microcirculatory network was studied in situ. The gastric tissue was used to quantify the percentage of damaged area, as well as myeloperoxidase (MPO), inducible nitric oxide synthase (iNOS), endothelial nitric oxide synthase (eNOS) protein and PPARγ protein and gene expression. Acid secretion was evaluated by the pylorus ligation model.
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