tilmicosin

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| ImageFile = Tilmicosin.svg

| ImageSize = 300px

| IUPACName = [(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

| OtherNames = Micotil; 20-Deoxy-20-(3,5-dimethylpiperidin-1-yl)-desmycosin[http://www.fao.org/docrep/W4601E/w4601e0e.htm Tilmicosin], United Nations Food and Agriculture Organization

|Section1={{Chembox Identifiers

| CASNo = 108050-54-0

| CASNo_Ref = {{cascite|correct|}}

| UNII = XL4103X2E3

| PubChem = 5282521

| ChemSpiderID = 4445656

| ChEMBL = 206342

| ChEBI = 195409

| 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

| 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

| InChIKey = JTSDBFGMPLKDCD-XVFHVFLVBD

| StdInChI = 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

| StdInChIKey = JTSDBFGMPLKDCD-XVFHVFLVSA-N

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|Section2={{Chembox Properties

| C=46 | H=80 | N=2 | O=13

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| Solubility = 566 mg/mL

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| Section6 = {{Chembox Pharmacology

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| ATCCode_prefix = J01

| ATCCode_suffix = FA91

| ATC_Supplemental =

| ATCvet = yes

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| Legal_CA = Rx-only

| Legal_CA_comment = {{cite web | title=Health product highlights 2021: Annexes of products approved in 2021 | website=Health Canada | date=3 August 2022 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-product-highlights-2021/appendices.html | access-date=25 March 2024}}

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|Section7={{Chembox Hazards

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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.[https://web.archive.org/web/20090710082244/http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm115928.pdf Micotil 300 New Animal Drug Application], United States Food and Drug Administration In humans, Tilmicosin causes fatal cardiotoxic effects at amounts greater than 1 milliliter when injected, something most commonly seen in veterinary personnel and farmers. [https://www.canada.ca/en/health-canada/services/drugs-health-products/veterinary-drugs/adverse-drug-reactions-adrs/micotil-tilmicosin.html Micotil (tilmicosin) - Adverse Drug Reactions - Veterinary Drugs], Veterinary Drugs Directorate 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.{{cite journal |last1=Gussow |first1=Leon |title=Toxicology Rounds: An Animal Antibiotic Lethal to Humans in Tiny Doses |journal=Emergency Medicine News |date=July 2020 |volume=42 |issue=7 |page=22 |doi=10.1097/01.EEM.0000688876.75898.6d |url=https://journals.lww.com/em-news/Fulltext/2020/07000/Toxicology_Rounds__An_Animal_Antibiotic_Lethal_to.16.aspx |access-date=5 April 2023 |ref=Human Micotil Toxicity|url-access=subscription }}