57381-26-7
Irsogladine
CAS: 57381-26-7
Molecular Formula: C9H7Cl2N5
57381-26-7 - Names and Identifiers
| Name | Irsogladine |
| Synonyms | Gaslon Irsogladin 57381-26-7 Irsogladine IRSOGLADINE Irsogladine free base 2',5'-Dichlorobenzoguanamine 5-triazine-2,4-diamine,6-(2,5-dichlorophenyl)-3 2,4-diamino-6-(2,5-dichlorophenyl)-1,3,5-triazine 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine 1,3,5-triazine-2,4-diamine, 6-(2,5-dichlorophenyl)- Irsogladine,2,4-DiaMino-6-(2,5-dichlorophenyl)-1,3,5-triazine |
| CAS | 57381-26-7 |
| InChI | InChI=1/C9H7Cl2N5/c10-4-1-2-6(11)5(3-4)7-14-8(12)16-9(13)15-7/h1-3H,(H4,12,13,14,15,16) |
57381-26-7 - Physico-chemical Properties
| Molecular Formula | C9H7Cl2N5 |
| Molar Mass | 256.09 |
| Density | 1.572 |
| Melting Point | 268-269°C |
| Boling Point | 552.2±60.0 °C(Predicted) |
| Flash Point | 287.8°C |
| Vapor Presure | 3.07E-12mmHg at 25°C |
| pKa | 3.88±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.706 |
| Physical and Chemical Properties | Colorless crystals from dioxane, melting point 268~269 ℃. Isogladine Maleate: C9H7C12N5? C4H4O4. [84504-69-8]. White or colorless crystal or crystalline powder, odorless, slightly bitter. Slightly soluble in methanol, ethanol, acetic acid or methyl acetate, very slightly soluble in ethyl acetate or ether, insoluble in chloroform or water. Melting point 205 °c (decomposition). Acute toxicity LD50 male and female mice, male and female rats (mg/kg):6035,5697,3898,2917 oral; 2841,3216,1600,1524 subcutaneous injection; 775,1006,558,545 intraperitoneal injection. |
| Use | For the treatment of gastric ulcer |
57381-26-7 - Nature
Open Data Verified Data
colorless crystals from dioxane, melting point 268-269 °c.
Last Update：2024-01-02 23:10:35
57381-26-7 - Preparation Method
Open Data Verified Data
2, 5-chlorotoluene was added to a 50% pyridine aqueous solution, potassium permanganate was slowly added with stirring, and the reaction was followed by treatment to obtain 2,5-= chlorobenzoic acid. 2,5-= chlorobenzoic acid, sulfamic acid and urea were heated together and treated to give 2,5-= chlorobenzonitrile. 2,5-= chlorobenzonitrile, cyanoguanidine, potassium hydroxide and ethylene glycol, stirred at 110 °c. After cooling, adding water, filtering, washing with water, recrystallization from methanol-Water, White isoradine is obtained, isoradine and maleic acid are refluxed in dioxane, cooling, filtering, washing with water, drying, recrystallization from anhydrous ethanol, white crystalline isoradine maleate was obtained.
Last Update：2022-01-01 09:23:13
57381-26-7 - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 3.905 ml | 19.524 ml | 39.049 ml |
| 5 mM | 0.781 ml | 3.905 ml | 7.81 ml |
| 10 mM | 0.39 ml | 1.952 ml | 3.905 ml |
| 5 mM | 0.078 ml | 0.39 ml | 0.781 ml |
Last Update：2024-01-02 23:10:35
57381-26-7 - Use
Open Data Verified Data
Japan New Drug Corporation research and development, in 1989. For gastric ulcer disease. Gastric mucosal protective agents, by strengthening the combination of gastric mucosal epithelial cells, inhibit epithelial cell detachment, shedding and cell gap expansion, enhance the stability of the mucosal cells themselves, in order to play the role of mucosal defense, inhibition of harmful substances through the mucosa. Has anti-ulcer effect, for the treatment of gastric ulcer, can also be used to improve acute gastritis, acute exacerbation of chronic gastritis gastric mucosal lesions.
Last Update：2022-01-01 09:23:13
57381-26-7 - Safety
Open Data Verified Data
isopetadine maleate, male and female mice, male and female rats LDso(mg/kg): 6035,5697,3898,2917 by mouth; 2841,3216,1600,1524 subcutaneous injection; 775, 1006,558,545 intraperitoneal injection.
Last Update：2022-01-01 09:23:14
57381-26-7 - Reference Information
| biological activity | Irsogladine is an anti-gastric ulcer agent that binds to the M1 muscarininc acetylcholine receptor, in favor of cell gap junctional communication. |
| Target | Value |
| Use | for gastric ulcer disease. for the treatment of gastric ulcer thiadiazole derivative; Pharmaceutical intermediates |
| production method | 2, 5-dichlorotoluene was added to 50% pyridine aqueous solution, potassium permanganate was slowly added with stirring, 65~70 deg C reaction. The solid was filtered off and pyridine was recovered. The precipitate was neutralized with dilute hydrochloric acid, filtered, washed with water and dried to give 2, 5-dichlorobenzoic acid in 77.5% yield. 2, 5-dichlorobenzoic acid, sulfamic acid and urea were heated to melt and reacted at 200 °c. After cooling, hot water was added and stirred. Filtration, washing with water, drying and recrystallization from ethanol gave 2, 5-dichlorobenzonitrile in 69.8% yield. 2, 5-dichlorobenzonitrile, cyanoguanidine, potassium hydroxide and ethylene glycol were stirred at 110 °c. After cooling, water was added, filtered, washed with water, and recrystallized from methanol-water to give white isoradine in 76.2% yield with a melting point of 268-270 °c. Isosoridine and maleic acid were refluxed in dioxane. Cool, filter, wash with water, and dry. Recrystallized from anhydrous ethanol to obtain white crystalline isoradine maleate with a yield of 86.0% and a melting point of 183-186 °c. |
Last Update：2024-04-10 22:29:15
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