prednimustine
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
- 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
Safety Information
- Hazardous Substances Data
- 29069-24-7(Hazardous Substances Data)
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