trofosfamide Chemical Properties

Melting point:

47-49°C

alpha 

D25 -28.6° (c = 2 in CH3OH)

Boiling point:

104°C

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

DMF: 50mg/mL; DMSO: 30mg/mL; Ethanol: 50mg/mL; PBS (pH 7.2): 10mg/mL

form 

A crystalline solid

pka

-0.46±0.20(Predicted)

Safety Information

Toxicity

LD50 i.p. in mice: 212 mg/kg (Brock, Potel)

trofosfamide Usage And Synthesis

Chemical Properties

Off-White Low Melting Solid

Originator

Ixoten,Asta,W. Germany,1973

Uses

Antineoplastic; one derivative

Definition

ChEBI: Trofosfamide is a member of ifosfamides.

Manufacturing Process

259 g (1 mol) of N,N-bis-(2-chloroethyl)-phosphoric acid amide dichloride, 209 g (1.2 mols) of N-(2-chloroethyl)-N-(3-hydroxypropyl)-amine hydrochloride (crude), 1,000 cc of ethylene dichloride and 344 g (3.4 mols) of triethylamine are the reactants. N,N-bis-(2-chloroethyl)-phosphoric acid amide dichloride is dissolved in the methylene dichloride. N-(2-chloroethyl)-N-(3- hydroxypropyl)-amine hydrochloride is suspended in this solution and triethylamine is added thereto dropwise with stirring. The temperature of the solution rises to boiling, After the termination of the addition, the mixture is heated to boiling for another 6 hours. Thereafter, the reaction mixture is cooled down and allowed to stand overnight at about 0°C. The precipitated triethylamine hydrochloride is filtered off with suction. The resulting solution is evaporated, the residue (about 370 g) is triturated with about 3.2 liters of ether and is heated to boiling for a short period of time.
The ethereal solution is decanted from the insolubles (about 90 g). The solution is rendered to pH 6.5 to 7 by the addition of ethereal hydrochloric acid and then is filtered over charcoal and thereafter is evaporated. During evaporation, the temperature should not rise above 40°C. The residue is dissolved in ether and in an amount corresponding to half of its weight (240 g of residue, dissolved in 120 cc of ether), the ethereal solution is cooled to - 5°C and is inoculated. After standing for 25 hours, 140 g have been separated by crystallization. After separation by filtration with suction, the mother liquor is diluted with ether to 5 times its volume, the solution is filtered over charcoal, is again evaporated and the residue is again dissolved in a volume corresponding to half of the weight of the residue. Another cooling to -5°C and inoculation produces further 18 g of the desired compound. MP: 50° to 51°C. Total yield: 161 g (50% of the theoretical)

Therapeutic Function

Cancer chemotherapy

Safety Profile

Poison by intraperitoneal, subcutaneous, and intravenous routes. Moderately toxic by ingestion. Human mutation data reported. Human systemic effects by unspecified routes: hematuria, leukopenia, and thrombocytopenia. When heated to decomposition it emits very toxic fumes of Cl-, NOx, and POx.

trofosfamide (22089-22-1)Related Product Information

• OXYPHENYL BUTAZONE
• Ammonium dihydrogen phosphate
• Cyclic adenosine monophosphate
• PHOSPHAMIDON
• Cyclophosphamide
• dechloroethylcyclophosphamide
• Ifosfamide
• trofosfamide
• dechloroethylifosfamide
• phosphoramide mustard