Chemistry: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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:195409
ChEMBL	ChEMBL206342
ChemSpider	4445656
PubChem CID	5282521
UNII	XL4103X2E3
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
1=ATCvet code}	QJ01FA91 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tracking categories (test):

• SizeSet

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. In humans, Tilmicosin causes fatal cardiotoxic effects at amounts greater than 1 milliliter when injected, something most commonly seen in veterinary personnel and farmers. 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.