6444. Nemadectin

Nomenclature

CAS number: 102130-84-7
[6R,23S,25S(E)]-5-O-Demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-hydroxymilbemycin B; antibiotic S-541A; LL-F-28249α; F-28249α; CL-287088.
C36H52O8; mol wt 612.79.
C 70.56%, H 8.55%, O 20.89%.

Description and references

Macrocyclic antibiotic produced by Streptomyces cyaneogriseus ssp. noncyanogenus and Streptomyces thermoachaensis. Structurally related to the milbemycins and the avermectins, q.q.v. Isoln: I. B. Wood et al., EP 170006; I. B. Wood, J. A. Pankavich, US 4869901 (1986, 1989 both to Am. Cyanamid). Chemical and structural characterization: G. T. Carter et al., Chem. Commun. 1987, 402; G. T. Carter et al., J. Antibiot. 41, 519 (1988). NMR spectroscopy: S. Rajan, G. W. Stockton, Magn. Reson. Chem. 27, 437 (1989). Antiparasitic activity in horses: E. T. Lyons et al., Am. J. Vet. Res. 50, 970 (1989); in dogs: M. E. Doscher et al., Vet. Parasitol. 34, 255 (1989); in sheep: J. A. Pankavich et al, Vet. Rec. 130, 241, (1992).

Chemical structure

Properties

White fluffy solid from tert-butanol. [α]D26 +133° (c = 0.3 in acetone). uv max (methanol): 244 nm, (log ε 4.47). Readily sol in common organic solvents. Practically insol in water.

Therapeutic Category (Veterinary)

Antiparasitic.