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
Identifiers
CAS Number	108050-54-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:195409;
ChEMBL	ChEMBL206342;
ChemSpider	4445656;
ECHA InfoCard	100.167.324
PubChem CID	5282521;
UNII	XL4103X2E3;
CompTox Dashboard (EPA)	DTXSID5046011 ;
	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;
	SMILES 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
Pharmacology
ATCvet code	QJ01FA91 (WHO)
Legal status	CA: ℞-only;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

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

[fao-1] 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.

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