Aminopropylamino)ethylsulfanylphosphonic acid trihydrate
Amifostine Trihydrate
CAS: 112901-68-5
Molecular Formula: C5H17N2O4PS
Aminopropylamino)ethylsulfanylphosphonic acid trihydrate - Names and Identifiers
Aminopropylamino)ethylsulfanylphosphonic acid trihydrate - Physico-chemical Properties
| Molecular Formula | C5H17N2O4PS |
| Molar Mass | 232.23 |
| Boling Point | 441.7℃ at 760 mmHg |
| Solubility | Water |
| Appearance | White powder |
| pKa | pKa1 <2.0; pKa2 4.2; pKa3 9.0; pKa4 11.7(at 25℃) |
| Storage Condition | 2-8°C |
| Use | Content determination |
Aminopropylamino)ethylsulfanylphosphonic acid trihydrate - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | TE6491000 |
| HS Code | 2930909165 |
Aminopropylamino)ethylsulfanylphosphonic acid trihydrate - Reference Information
| Overview | Amifostine is a broad-spectrum cytoprotective agent. It was once used as a military anti-radiation agent and is now used as a protective agent for radiotherapy and chemotherapy. It is effective in reducing the side effects of anti-cancer drugs such as cyclophosphamide, chloramoplatin, doxorubicin and anti-HIV drugs such as 3-azido-3-deoxythymidine, and does not affect the anticancer drugs or anti-HIV drugs Efficacy. At present, the commercially available amifostine products include freeze-dried powder injection produced by American Life Sciences Co., Ltd. under the trade name ETHYOL. The product has only freeze-dried powder injection, but this amorphous form produced by low-pressure freeze-drying is thermally unstable. |
| preparation | step 1: synthesis adding 13.6kg of pure water and 19.2mol(7.6kg) of sodium thiophosphate dodecahydrate into a 50L stainless steel reactor, adding 19.8mol(6.8kg,3% excess) of N-(2-bromoethyl)-1,3-propylenediamine dihydrobromate under stirring, and slowly adding 11.0kgDMSO, at the same time, the reaction temperature should not exceed 25 ℃. After dropping DMSO, monitor the reaction solution with silver nitrate solution until no black precipitate is precipitated, the reaction is over, the reaction solution is cooled to 0 ℃, stirred for 5 minutes per hour, and maintained for 18 hours. Centrifugal filtration to obtain 6.1kg of crude amifostine trihydrate. Step 2: for the first recrystallization and purification, 22.0kg of pure water is added into a 50L stainless steel crystallization kettle, 6.1kg of crude 3-aminopropylamine ethyl thiophosphoric acid prepared in the previous step is added, dissolved at room temperature, 95.0g of activated carbon is added, stirred at room temperature for 15 minutes, filtered, 8.7kg of methanol is added into the mother liquor, cooled to 0 ℃ by cooling water, maintained for 18 hours, centrifugally filtered, one-time recrystallization refined crystal-free water 3-aminopropylamine ethyl thiophosphoric acid 4.8kg. Step 3: for the second recrystallization and purification, 20.0kg of pure water is added into a 50L stainless steel crystallization kettle, 4.8kg of crystal-free water obtained by the first recrystallization, stirring and dissolving at room temperature, adding 75.0g of activated carbon, stirring for 15 minutes at room temperature, filtering, adding 3.2kg of ethanol to the mother liquor, cooling water to 0 ℃, maintaining for 18 hours, centrifugal filtration, and vacuum drying at 30 ℃, 3.6kg of amifostine trihydrate was obtained. HPLC method (according to the 29th edition of the United States Pharmacopoeia method) analysis, the purity is 99.81%, the mercaptan content is 0.021%, and other related substances are 0.078%. |
| biological activity | Amifostine trihydrate is the first approved anti-radiation drug to reduce the risk of kidney disease caused by cisplatin treatment. |
| use | can be used as an adjuvant therapeutic agent for tumor radiotherapy or cytotoxic chemotherapy |
Last Update：2024-04-10 22:29:15
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