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prednimustine

Basic information Safety Supplier Related

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
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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
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Safety Information

Hazardous Substances Data
29069-24-7(Hazardous Substances Data)
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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

prednimustineSupplier

LGM Pharma
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Shaanxi Dideu Newmaterial Co., Ltd.
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