Brief introduction
Tilmicosin is a relatively novel semi-synthetic macrolide antibiotics derived from tylosin for being applied to livestock and poultry. The chemical name is 4A-O-de (2, 6-dideoxy-methyl-3-C--L-ribose-pyran-hexyl)-20-deoxy-20-(3,5-dimethyl-1-piperidinyl)-[20 (cis: trans)] tylosin. Molecule formula is C46H80N2O13 and the molecular weight of 869.15.
Tilmicosin has a similar antibacterial spectrum as tylosin but has enhanced effect on the anti-Pasteurella multocida and hemolytic pasteurella. It was successfully developed in 1980s and initially used with a code of EL-870. Common trade names include Pulmotil © Micotil ©, preparations include tilmicosin soluble powder, premix (20%) preparation, and injection. In 1990 it was approved in most European countries; it was approved in the US in 1992, and included in USP. China also has some domestic enterprises approved for production of tilmicosin.
Because of its special antibacterial activity and pharmacokinetic characteristics, the drug has been approved for clinical prevention and treatment of infectious diseases for cattle, goats, sheep, cows, pigs, and chickens. It is especially applied to the treatment of respiratory diseases of livestock, such as cattle Actinobacillus pleuropneumonia, Pasteurella disease, chicken mycoplasmosis and mastitis of lactating animals.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
Chemical Properties
It is white or white powder with humidity: ≤5.0%.
Uses
It can be used as anti-bacterial.
It is mainly used for the treatment of infection caused by pleuropneumonia, Actinobacillus, Pasteurella and mycoplasma.
Chemical Properties
White Solid
Uses
A Macrolide antibiotic.
Uses
Macrolide antibiotic structurally related to tylosin. Antibacterial
Uses
Tilmicosin is a semi-synthetic antibiotic derived from desmycosin (tylosin B), a minor co-metabolite of tylosin. Tilmicosin is produced by reductive amination of desmycosin. Desmycosin itself is prepared by the partial hydrolysis of tylosin with the loss of the mycarosyl sugar. The piperidinyl group at C20 of tilmicosin provides a wider spectrum of antibiotic action, in particular good protection against Pasteurella in livestock.
Preparation
The synthesis of tilmicosin starts with the
removal of the sugar mycarose from tylosin by acid
hydrolysis to give desmycosin. Reductive amination of
the aldehyde at C-20 of desmycosin with 3,5-dimeth
ylpiperidine via a Wallach reaction or a metal hydride
(e.g., NaBH3CN) completes the synthesis to give tilmi
cosin[1].
Veterinary Drugs and Treatments
Tilmicosin is indicated for the treatment of bovine or ovine respiratory
diseases (BRD) caused by Mannheimia (Pasturella) haemolytica.
References
[1]
Willard, K. E., Kirst, H. A., Leeds, J. P., Readnour, R. S., Klink, P. R., Cleveland, C. M., Kiehl, D. E. (1998). Identification and Synthesis of an Oxidation Product of Tilmicosin. Journal of Agricultural and Food Chemistry, 46(8), 3265–3271.
https://doi.org/10.1021/jf9710746
