Tilmicosin

Tilmicosin is a macrolide antibiotic. It is distributed under the brand name Micotil. It is used in veterinary medicine for the treatment of bovine respiratory disease and enzootic pneumonia caused by Mannheimia (Pasteurella) haemolytica in sheep.[2] In humans, Tilmicosin causes fatal cardiotoxic effects at amounts greater than 1 milliliter when injected, something most commonly seen in veterinary personnel and farmers. [3] Tilmicosin, like most macrolides, is a Calcium channel blocker. However, because Micotil is formulated for animals like cows, it has exceptionally more epotent Ca channel blocking effects in humans with a dose of .5 mL causing significant poisoning and a dose of 5-6 ml being lethal.[4]

Tilmicosin
Names
IUPAC name
[(2R,3R,4E,6E,9R,11R,12S,13S,14R)-12-{[3,6-Dideoxy-3-(dimethylamino)-β-D-glucopyranosyl]oxy}-11-{2-[(3R,5S)-3,5-dimethylpiperidin-1-yl]ethyl}-2-ethyl-14-hydroxy-5,9,13-trimethyl-8,16-dioxooxacyclohexadeca-4,6-dien-3-yl]methyl 6-deoxy-2,3-di-O-methyl-β-D-allopyranoside
Other names
Micotil; 20-Deoxy-20-(3,5-dimethylpiperidin-1-yl)-desmycosin[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.167.324
UNII
  • InChI=1S/C46H80N2O13/c1-13-36-33(24-57-46-44(56-12)43(55-11)40(53)31(8)59-46)19-25(2)14-15-34(49)28(5)20-32(16-17-48-22-26(3)18-27(4)23-48)42(29(6)35(50)21-37(51)60-36)61-45-41(54)38(47(9)10)39(52)30(7)58-45/h14-15,19,26-33,35-36,38-46,50,52-54H,13,16-18,20-24H2,1-12H3/b15-14+,25-19+/t26-,27+,28-,29+,30-,31-,32+,33-,35-,36-,38+,39-,40-,41-,42-,43-,44-,45+,46-/m1/s1
    Key: JTSDBFGMPLKDCD-XVFHVFLVSA-N
  • InChI=1/C46H80N2O13/c1-13-36-33(24-57-46-44(56-12)43(55-11)40(53)31(8)59-46)19-25(2)14-15-34(49)28(5)20-32(16-17-48-22-26(3)18-27(4)23-48)42(29(6)35(50)21-37(51)60-36)61-45-41(54)38(47(9)10)39(52)30(7)58-45/h14-15,19,26-33,35-36,38-46,50,52-54H,13,16-18,20-24H2,1-12H3/b15-14+,25-19+/t26-,27+,28-,29+,30-,31-,32+,33-,35-,36-,38+,39-,40-,41-,42-,43-,44-,45+,46-/m1/s1
    Key: JTSDBFGMPLKDCD-XVFHVFLVBD
  • O=C4\C=C\C(=C\[C@H](CO[C@@H]1O[C@H](C)[C@@H](O)[C@@H](OC)[C@H]1OC)[C@H](OC(=O)C[C@@H](O)[C@@H]([C@@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](N(C)C)[C@H]2O)C)[C@@H](CCN3C[C@H](C)C[C@H](C)C3)C[C@H]4C)C)CC)C
Properties
C46H80N2O13
Molar mass 869.147 g·mol−1
566 mg/mL[1]
Pharmacology
QJ01FA91 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Tilmicosin, United Nations Food and Agriculture Organization
  2. Micotil 300 New Animal Drug Application, United States Food and Drug Administration
  3. Micotil (tilmicosin) - Adverse Drug Reactions - Veterinary Drugs, Veterinary Drugs Directorate
  4. Gussow, Leon (July 2020). "Toxicology Rounds: An Animal Antibiotic Lethal to Humans in Tiny Doses". Emergency Medicine News. 42 (7): 22. doi:10.1097/01.EEM.0000688876.75898.6d. Retrieved 5 April 2023.
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