9810. Tulathromycin

Nomenclature

Draxxin (Pfizer).
C41H79N3O12; mol wt 806.08.
C 61.09%, H 9.88%, N 5.21%, O 23.82%.

Description and references

Triamilide antibiotic for treatment of bovine and porcine respiratory disease. Exists as an equilibrium mixture of two isomeric forms, tulathromycin A (~90%) and B (~10%). HPLC determn in livestock plasma and lung homogenates: D. Gáler et al., J. Agric. Food Chem. 52, 2179 (2004). Pharmacokinetics in cattle: M. A. Nowakowski et al., Vet. Ther. 5, 60 (2004); in swine: H. A. Benchaoui et al., J. Vet. Pharmacol. Ther. 27, 203 (2004).

Chemical structure

Derivative

Tulathromycin A.

Nomenclature

CAS number: 217500-96-4
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[[2,6-Dideoxy-3-C-methyl-3-O-methyl-4-C-[(propylamino)methyl]-α-l-ribo-hexopyranosyl]oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-d-xylo-hexopyanosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one; CP-472295.

Description and references

Prepn: B. S. Bronk et al., WO 9856802; eidem, US 6420536 (1998, 2002 both to Pfizer); and crystal structure: M. A. Letavic et al., Bioorg. Med. Chem. Lett. 12, 2771 (2002).

Derivative

Tulathromycin B.

Nomenclature

CAS number: 280755-12-6
(2R,3R,6R,8R,9R,10S,11S,12R)-11-[[2,6-Dideoxy-3-C-methyl-3-O-methyl-4-C-[(propylamino)methyl]-α-l-ribo-hexopyranosyl]oxy]-2-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-8-hydroxy-3,6,8,10,12-pentamethyl-9-[[3,4,6-trideoxy-3-(dimethylamino)-β-d-xylo-hexopyanosyl]oxy]-1-oxa-4-azacyclotridecan-13-one; CP-547272.

Description and references

Prepn: R. J. Rafka et al., WO 0031097; eidem, US 6329345 (2000, 2001 both to Pfizer).

Therapeutic Category (Veterinary)

Antibacterial.