4596. Halofuginone

Nomenclature

CAS number: 55837-20-2
rel-7-Bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone; (±)-trans-7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)acetonyl]-4(3H)-quinazolinone; 7-bromo-6-chlorofebrifugine; HAL.
C16H17BrClN3O3; mol wt 414.68.
C 46.34%, H 4.13%, Br 19.27%, Cl 8.55%, N 10.13%, O 11.57%.

Description and references

Halogenated deriv of febrifugine, q.v. Prepn: E. Waletzky et al., US 3320124 (1967 to Am. Cyanamid). In vivo and in vitro activity: J. G. Ryley et al., Parasitology 70, 203 (1975). Toxicity to fresh water organisms: Bull. Environ. Contam. Toxicol. 15, 720 (1976). HPLC determn in chicken feed: A. Anderson et al., J. Chromatogr. 168, 471 (1979); in chicken serum: R. C. Beier et al., J. Liq. Chromatogr. 17, 2961 (1994). Evaluation as coccidiostat: P. E. Waibel et al., Poult. Sci. 66, 1629 (1987). Inhibition of collagen synthesis and effect on skin tearing: I. Granot et al., ibid. 70, 1559 (1991).

Chemical structure

Derivative

Hydrobromide.

Nomenclature

CAS number: 64924-67-0
RU-19110; Stenorol (Intervet).
C16H17BrClN3O3.HBr; mol wt 495.59.
C 38.78%, H 3.66%, Br 32.25%, Cl 7.15%, N 8.48%, O 9.69%.

Properties

Crystals, mp 247° (dec).

Therapeutic Category (Veterinary)

Antiprotozoal (coccidiostat).