6919. Oxamniquine

Nomenclature

CAS number: 21738-42-1
1,2,3,4-Tetrahydro-2-[[(1-methylethyl)amino]methyl]-7-nitro-6-quinolinemethanol; 1,2,3,4-tetrahydro-2-[(isopropylamino)methyl]-7-nitro-6-quinolinemethanol; 6-hydroxymethyl-2-isopropylaminomethyl-7-nitro-1,2,3,4-tetrahydroquinoline; UK-4271; Mansil (Pfizer); Vansil (Pfizer).
C14H21N3O3; mol wt 279.33.
C 60.20%, H 7.58%, N 15.04%, O 17.18%.

Description and references

Prepn: H. C. Richards, ZA 6803636; idem, US 3821228 (1967, 1974 both to Pfizer). Discovery of schistosomicidal activity: H. C. Richards, R. Foster, Nature 222, 581 (1969). Metabolism: N. M. Woolhouse, B. Kaye, Parasitology 15, 111 (1977). Genetic activity: T. M. Ong, Mutat. Res. 55, 43 (1978). In vitro activity: C. J. Chavasse et al., Ann. Trop. Med. Parasitol. 72, 293 (1978). Mutagenicity study: R. P. Batzinger, E. Bueding, J. Pharmacol. Exp. Ther. 200, 1 (1977). Pharmacology: R. Foster, Rev. Inst. Med. Trop. Sao Paulo 15, Suppl. 1, 189 (1973), C.A. 83, 188417g (1975). Clinical study: R. J. Pitchford, M. Lewis, S. Afr. Med. J. 53, 677 (1978). HPLC determn in biological fluids: H. W. Jun, M. A. Radwan, Anal. Lett. 18, 1345 (1985). Comprehensive description: I. Ahmad, et al., Anal. Profiles Drug Subs. 20, 601-625 (1991).

Chemical structure

Properties

Pale yellow crystals from isopropanol, mp 147-149°. Sol in acetone, chloroform and methanol. Sol in about 3300 parts of water at 27°C. pH of a 1% soln 8.0-10.0. uv max (methanol) 205.5, 249.5, 389.5 nm (A1%1cm 486, 695, 62.5). LD50 in mice, rabbits (mg/kg): >2000, >1000 i.m., 1300, 800 orally (Foster).

Therapeutic Category

Anthelmintic (Schistosoma).

Keywords

Anthelmintic (Schistosoma)