Tilmicosin

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
CAS Number
  • 108050-54-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:195409
ChEMBL
  • ChEMBL206342
ChemSpider
  • 4445656
ECHA InfoCard 100.167.324 Edit this at Wikidata
PubChem CID
  • 5282521
UNII
  • XL4103X2E3
CompTox Dashboard (EPA)
  • DTXSID5046011 Edit this at Wikidata
InChI
  • 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
Chemical formula
 C46H80N2O13
Molar mass 869.147 g·mol−1
Solubility in water
 566 mg/mL[1]
Pharmacology
QJ01FA91 (WHO)
Legal status
  • CA: ℞-only[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

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.[3] In humans, Tilmicosin causes fatal cardiotoxic effects at amounts greater than 1 milliliter when injected, something most commonly seen in veterinary personnel and farmers. [4] Tilmicosin, like most macrolides, is a Calcium channel blocker. However, because Micotil is formulated for animals like cows, it has exceptionally more potent Ca channel blocking effects in humans with a dose of .5 mL causing significant poisoning and a dose of 5-6 ml being lethal.[5]

References

  1. ^ a b Tilmicosin, United Nations Food and Agriculture Organization
  2. ^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
  3. ^ Micotil 300 New Animal Drug Application, United States Food and Drug Administration
  4. ^ Micotil (tilmicosin) - Adverse Drug Reactions - Veterinary Drugs, Veterinary Drugs Directorate
  5. ^ 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.