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| CAS No.: | 111025-46-8 |
|---|---|
| Name: | Pioglitazone |
| Molecular Structure: | |
|
|
|
| Formula: | C19H20N2O3S |
| Molecular Weight: | 356.445 |
| Synonyms: | 5-[4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl]thiazolidine-2,4-dione;Pioglitazone;Zactos; |
| EINECS: | 601-029-7 |
| Density: | 1.26 g/cm3 |
| Melting Point: | 183-184 °C |
| Boiling Point: | 575.4 °C at 760 mmHg |
| Flash Point: | 301.8 °C |
| Solubility: | Soluble in DMF; slightly soluble in ethanol; practically insoluble in water |
| Appearance: | Colorless needle crystal |
| Hazard Symbols: |
 F, C
|
| Risk Codes: | 11-34 |
| Safety: | 16-26-36/37/39-45 |
| PSA: | 93.59000 |
| LogP: | 4.29040 |
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Specification
The IUPAC name of Pioglitazone is 5-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione. With the CAS registry number 111025-46-8, it is also named as Actos. The classification code is Hypoglycemic agents. It is colorless needle crystal which is a prescription drug of the class thiazolidinedione (TZD) with hypoglycemic (antihyperglycemic, antidiabetic) action. Additioanlly, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.94; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.57; (4)ACD/LogD (pH 7.4): 1.89; (5)ACD/BCF (pH 5.5): 43.12; (6)ACD/BCF (pH 7.4): 9.04; (7)ACD/KOC (pH 5.5): 404.11; (8)ACD/KOC (pH 7.4): 84.69; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.611; (13)Molar Refractivity: 98.21 cm3; (14)Molar Volume: 282.7 cm3; (15)Polarizability: 38.93×10-24 cm3; (16)Surface Tension: 54.9 dyne/cm; (17)Enthalpy of Vaporization: 86.19 kJ/mol; (18)Vapour Pressure: 3.03E-13 mmHg at 25°C; (19)Rotatable Bond Count: 7; (20)Tautomer Count: 10; (21)Exact Mass: 356.119463; (22)MonoIsotopic Mass: 356.119463; (23)Topological Polar Surface Area: 93.6; (24)Complexity: 466.
Preparation of Pioglitazone: The condensation of 2-(5-ethyl-2-pyridyl) ethanol (Ⅰ) and p-fluorine nitrobenzene produced compound (Ⅱ). Then it is reduced to amine (Ⅲ). And then the diazotization in acetone-methanol containing HBr and coupling by adding methyl acrylate to produce compound (Ⅳ). And the condensation cyclization with thiourea and hydrolysis obtain the product.
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Uses of Pioglitazone: It is used for the treatment of diabetes mellitus type 2 in monotherapy and in combination with a sulfonylurea, metformin, or insulin. And it has also been used to treat non-alcoholic steatohepatitis (fatty liver), but this use is presently considered experimental. But it is ineffective and possibly harmful in diabetes mellitus type 1 and diabetic ketoacidosis. And it has many side effects. This drug can cause fluid retention and peripheral edema.
When you are using this chemical, please be cautious about it as the following:
It is highly flammable and can cause burns, so people should keep it away from sources of ignition. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
1. SMILES:O=C1NC(=O)SC1Cc3ccc(OCCc2ncc(cc2)CC)cc3
2. InChI:InChI=1/C19H20N2O3S/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)