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| | prednimustine Basic information |
| Product Name: | prednimustine | | Synonyms: | prednimustine;Prednimustin;21-[4-[p-[Bis(2-chloroethyl)amino]phenyl]-1-oxobutoxy]-11β,17-dihydroxypregna-1,4-diene-3,20-dione;Chlorambucil prednisolone ester;LEO-1031;NSC-134087;Stereocyt;NSC 171345 | | CAS: | 29069-24-7 | | MF: | C35H45Cl2NO6 | | MW: | 646.64 | | EINECS: | 249-410-3 | | Product Categories: | | | Mol File: | 29069-24-7.mol |  |
| | prednimustine Chemical Properties |
| Melting point | 163-164° | | alpha | D24 +92.9° (c = 1.06 in chloroform) | | Boiling point | 791.5±60.0 °C(Predicted) | | density | 1.30±0.1 g/cm3(Predicted) | | pka | 12.32±0.70(Predicted) | | IARC | 3 (Vol. 50) 1990 |
| | prednimustine Usage And Synthesis |
| Originator | Stereocyt, Bellon ,France ,1978 | | Uses | Antineoplastic. | | Definition | ChEBI: Prednimustine is a corticosteroid hormone. | | Manufacturing Process | p-[N-bis(β-chloroethyl)amino] phenyl butyric acid was dissolved in a mixture of 150 ml dry benzene and 8.04 ml dry pyridine. The solution was cooled in an ice bath, and a solution of thionyl chloride in 30 ml dry benzene was slowly added with stirring under anhydrous conditions.
The reaction mixture was then kept at room temperature for 1 hour and thereafter poured into a mixture of 5.0 N HCl and crushed ice. The benzene solution was immediately washed with water, with cold 1.0 N NaHCO3 and finally with cold water. After drying over anhydrous sodium sulfate, the benzene was removed in vacuo. The residue is the p-[N-bis(βchloroethyl)amino]phenyl butyric anhydride which could be used without any further purification.
To a solution of 42.0 g of p-[N-bis(β-chloroethyl)amino]phenyl butyric anhydride in 500 ml dry pyridine was added 24.4 g of prednisolone. The reaction mixture was kept at room temperature for 24 hours under anhydrous condition. It was then poured into a mixture of concentrated HCl and crushed ice and extracted with ether-ethyl acetate (1:1).
The organic phase was washed several times with cold 1.0 N K2CO3 and finallywater. After drying over CaCl2 the solvent was removed in vacuo.
The residue is prednisolone 21-[4'-[p-bis(β-chloroethyl)amino]phenyl]butyrate which after crystallization from methanol/water had a melting point of 163°C to 164°C. | | Therapeutic Function | Cancer chemotherapy |
| | prednimustine Preparation Products And Raw materials |
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