| Identification | Back Directory | [Name]
prednimustine | [CAS]
29069-24-7 | [Synonyms]
LEO-1031
Sterecyt
Stereocyt
NSC 171345
NSC-134087
Prednimustin
prednimustine
prednimustine USP/EP/BP
HFVNWDWLWUCIHC-GUPDPFMOSA-N
Chlorambucil prednisolone ester
Prednisolone chloraMbucil ester
21-[4-[p-[Bis(2-chloroethyl)amino]phenyl]-1-oxobutoxy]-11β,17-dihydroxypregna-1,4-diene-3,20-dione
Pregna-1,4-diene-3,20-dione, 21-[4-[4-[bis(2-chloroethyl)amino]phenyl]-1-oxobutoxy]-11,17-dihydroxy-, (11β)- | [EINECS(EC#)]
249-410-3 | [Molecular Formula]
C35H45Cl2NO6 | [MDL Number]
MFCD00866487 | [MOL File]
29069-24-7.mol | [Molecular Weight]
646.64 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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