9768. Trofosfamide

Nomenclature

CAS number: 22089-22-1
N,N,3-Tris(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide; 2-[bis(2-chloroethyl)amino]-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxaphosphorine 2-oxide; N,N,N′-tris(2-chloroethyl)-N′,O-propylene phosphoric acid ester diamide; trilophosphamide; trophosphamide; NSC-109723; Z-4828; Ixoten (Baxter).
C9H18Cl3N2O2P; mol wt 323.58.
C 33.41%, H 5.61%, Cl 32.87%, N 8.66%, O 9.89%, P 9.57%.

Description and references

The 3-(2-chloroethyl) deriv of cyclophosphamide, q.v. Prepn: GB 1188159, C.A. 73, 44892d (1970); Arnold et al., DE 2107936, C.A. 77, 152238m (1972) (1970, 1972 both to Asta-Werke); K. Pankiewicz et al., J. Am. Chem. Soc. 101, 7712 (1979). Pharmacology: N. Brock, Int. Congr. Chemother., Proc. 5th, K. H. Spitzy, H. Haschek, Eds. (Verlag Wiener Med. Akad., Vienna, 1967) II(1), pp 155-161; J. Potel, N. Brock, Arzneim.-Forsch. 21, 1250 (1971); N. Brock, J. Potel, ibid. 24, 1149 (1974); Harrison, Fuquay, Proc. Soc. Exp. Biol. Med. 139, 957 (1972). Crystal and molecular structure: A. Perales, S. Garcia-Blanco, Acta Crystallogr. 33B, 1939 (1977).

Chemical structure

Properties

Crystals from ether, mp 50-51°. [α]D25 28.6° (c = 2 in CH3OH). LD50 i.p. in mice: 212 mg/kg (Brock, Potel).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkylating Agents; Nitrogen Mustards