7161. Perfosfamide

Nomenclature

CAS number: 62435-42-1; 39800-16-3 (unspecified stereo)
rel-(2R,4R)-2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl hydroperoxide P-oxide; cis-(±)-2-[bis(2-chloroethyl)amino]-4-hydroperoxytetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide; cis-4-hydroperoxycyclophosphamide; 4-HC; NSC-181815; Pergamid (Scios-Nova).
C7H15Cl2N2O4P; mol wt 293.08.
C 28.69%, H 5.16%, Cl 24.19%, N 9.56%, O 21.84%, P 10.57%.

Description and references

Prepn (stereochem. unspecified): NL 7208895; A. Takamizawa, T. Iwata, US 3808297 (1972, 1974 both to Shionogi); idem et al., J. Am. Chem. Soc. 95, 985 (1973). Structural study: A. Camerman et al., Acta Crystallogr. B33, 678 (1977). Cytostatic activity: A. Takamizawa et al., J. Med. Chem. 18, 376 (1975). Clinical use: D. Biggs et al., Prog. Clin. Biol. Res. 389, 9 (1994). Review of use as purging agent in autologous bone marrow transplantation: A. M. Yeager et al., Am. J. Pediatr. Hematol. Oncol. 12, 245-256 (1990); R. J. Jones, J. Hematother. 1, 343-348 (1992).

Chemical structure

Properties

White crystals from acetone/ether (unspecified form). mp 107-108°. LD50 in rats, mice (mg/kg): 115, 235 i.v.; 131, 181 i.p. (Takamizawa, 1975).

Therapeutic Category

Antineoplastic; bone marrow purging agent.

Keywords

Antineoplastic; Alkylating Agents; Nitrogen Mustards