9439. Tilmicosin

Nomenclature

CAS number: 108050-54-0
4A-O-De(2,6-dideoxy-3-C-methyl-α-l-ribo-hexopyranosyl)-20-deoxo-20-(3,5-dimethyl-1-piperidinyl)tylosin; 20-deoxo-20-(3,5-dimethylpiperidin-1-yl)desmycosin; EL-870; LY-177370; Micotil (Elanco); Pulmotil (Elanco).
C46H80N2O13; mol wt 869.13.
C 63.57%, H 9.28%, N 3.22%, O 23.93%.

Description and references

Macrolide antibiotic; structurally related to tylosin, q.v. Prepd as 85:15 mixture of cis/trans isomers: M. Debono, H. A. Kirst, EP 103465; eidem, US 4820695 (1984, 1989 both to Lilly); M. Debono et al., J. Antibiot. 42, 1253 (1989). In vitro antibacterial activity: E. E. Ose, ibid. 40, 190 (1987). Metabolism and tissue residue studies in cattle: A. L. Donoho et al., ACS Symp. Ser. 503, 158-167 (1992). Trial in treatment of calf pneumonia: E. E. Ose, L. V. Tonkinson, Vet. Rec. 123, 367 (1988). Prophylactic efficacy in bovine respiratory tract disease: D. W. Morck et al., J. Am. Vet. Med. Assoc. 202, 273 (1993).

Chemical structure

Properties

uv max: 283 nm (ε 22643). pKa′ (66% DMF): 7.4, 8.5. [α]D23 +12.75° (c = 0.010004 in CHCl3, 5 cm).

Therapeutic Category (Veterinary)

Antibacterial.