Tilmicosin
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Basic Info
| Common Name | Tilmicosin(F06169) |
| 2D Structure | |
| FRCD ID | F06169 |
| CAS Number | 108050-54-0 |
| PubChem CID | 5282521 |
| Formula | C46H80N2O13 |
| IUPAC Name | (4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-[(2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-7-[2-[(3S,5R)-3,5-dimethylpiperidin-1-yl]ethyl]-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-1-oxacyclohexadeca-11,13-diene-2,10-dione |
| InChI Key | JTSDBFGMPLKDCD-XVFHVFLVSA-N |
| 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 |
| Canonical SMILES | CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)O)N(C)C)O)CCN3CC(CC(C3)C)C)C)C)COC4C(C(C(C(O4)C)O)OC)OC |
| Isomeric SMILES | CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O)N(C)C)O)CCN3C[C@@H](C[C@@H](C3)C)C)C)\C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC |
| Synonyms |
Tilmicosin
Micotil
Micotil 300
108050-54-0
Tilmicosine [INN-French]
Tilmicosinum [INN-Latin]
Tilmicosina [INN-Spanish]
UNII-XL4103X2E3
HSDB 7446
C46H80N2O13
|
| Classifies |
Predicted: Veterinary Drug
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbohydrates and carbohydrate conjugates |
| Intermediate Tree Nodes | Aminosaccharides |
| Direct Parent | Aminoglycosides |
| Alternative Parents |
|
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Aminoglycoside core - Macrolide - Glycosyl compound - O-glycosyl compound - Piperidine - Oxane - Monosaccharide - 1,2-aminoalcohol - Amino acid or derivatives - Carboxylic acid ester - Ketone - Lactone - Cyclic ketone - Tertiary aliphatic amine - Tertiary amine - Secondary alcohol - Acetal - Carboxylic acid derivative - Dialkyl ether - Ether - Oxacycle - Azacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Alcohol - Aldehyde - Amine - Organopnictogen compound - Organonitrogen compound - Organic oxide - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 869.147 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 15 |
| Rotatable Bond Count | 12 |
| Complexity | 1420 |
| Monoisotopic Mass | 868.566 |
| Exact Mass | 868.566 |
| XLogP | 3.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 61 |
| Defined Atom Stereocenter Count | 19 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9823 |
| Human Intestinal Absorption | HIA- | 0.6896 |
| Caco-2 Permeability | Caco2- | 0.6082 |
| P-glycoprotein Substrate | Substrate | 0.9020 |
| P-glycoprotein Inhibitor | Inhibitor | 0.9362 |
| Inhibitor | 0.8105 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7977 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6053 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8663 |
| CYP450 2D6 Substrate | Non-substrate | 0.8822 |
| CYP450 3A4 Substrate | Substrate | 0.6459 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9020 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9147 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8908 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8797 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9215 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9815 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8220 |
| Non-inhibitor | 0.6280 | |
| AMES Toxicity | Non AMES toxic | 0.7446 |
| Carcinogens | Non-carcinogens | 0.9339 |
| Fish Toxicity | High FHMT | 0.9053 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9875 |
| Honey Bee Toxicity | Low HBT | 0.6017 |
| Biodegradation | Not ready biodegradable | 0.6247 |
| Acute Oral Toxicity | III | 0.7234 |
| Carcinogenicity (Three-class) | Non-required | 0.4812 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.4613 | LogS |
| Caco-2 Permeability | 0.3766 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5426 | LD50, mol/kg |
| Fish Toxicity | 1.4340 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5720 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Aquatic Animal | Japan | 0.05ppm | |||
| Crustaceans | Japan | 0.05ppm | |||
| Shelled Molluscas | Japan | 0.05ppm | |||
| Other Fish | Japan | 0.05ppm | |||
| Perciformes | Japan | 0.05ppm | |||
| Anguilliformes | Japan | 0.05ppm | |||
| Salmoniformes | Japan | 0.05ppm | |||
| Other Poultry Animals,Edible Offal | Japan | 0.3ppm | |||
| Chicken,Edible Offal | Japan | 0.3ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.3ppm | |||
| Chicken,Kidney | Japan | 0.3ppm | |||
| Other Poultry Animals,Liver | Japan | 1ppm | |||
| Chicken,Liver | Japan | 1ppm | |||
| Other Poultry Animals,Fat | Japan | 0.08ppm | |||
| Chicken,Fat | Japan | 0.08ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.08ppm | |||
| Chicken,Muscle | Japan | 0.08ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 1ppm | |||
| Sheep,Edible Offal | Japan | 0.3ppm | |||
| Pig,Edible Offal | Japan | 1ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Noncovalent Interaction of Tilmicosin with Bovine Serum Albumin. | Molecules | 2018 Jul 31 | 30065238 |
| Prevalence and Characterization of <i>Staphylococcus aureus</i> Cultured From Raw Milk Taken From Dairy Cows With Mastitis in Beijing, China. | Front Microbiol | 2018 | 29988423 |
| Antibiofilm and antibacterial effects of specific chitosan molecules onStaphylococcus aureus isolates associated with bovine mastitis. | PLoS One | 2017 May 9 | 28486482 |
| Detection of antibiotics in chicken eggs obtained from supermarkets in Ho ChiMinh City, Vietnam. | J Environ Sci Health B | 2017 Jun 3 | 28281880 |
| Mycoplasma bovis isolates from dairy calves in Japan have less susceptibilitythan a reference strain to all approved macrolides associated with a pointmutation (G748A) combined with multiple species-specific nucleotide alterationsin 23S rRNA. | Microbiol Immunol | 2017 Jun | 28504455 |
| Effects of nasal instillation of a nitric oxide-releasing solution or parenteral administration of tilmicosin on the nasopharyngeal microbiota of beef feedlotcattle at high-risk of developing respiratory tract disease. | Res Vet Sci | 2017 Dec | 28231472 |
| Risk-based approach to developing a national residue sampling plan for testingunder European Union regulation for veterinary medicinal products andcoccidiostat feed additives in domestic animal production. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016Jul | 27189753 |
| Whole Genome Sequence Analysis of Pig Respiratory Bacterial Pathogens withElevated Minimum Inhibitory Concentrations for Macrolides. | Microb Drug Resist | 2016 Oct | 26981707 |
| Separation analysis of macrolide antibiotics with good performance on apositively charged C18HCE column. | J Sep Sci | 2016 Mar | 26782089 |
| Antimicrobial susceptibility of Mycoplasma bovis isolates from veal calves anddairy cattle in the Netherlands. | Vet Microbiol | 2016 Jun 30 | 27259820 |
| Antimicrobial resistance genes in Actinobacillus pleuropneumoniae, Haemophilusparasuis and Pasteurella multocida isolated from Australian pigs. | Aust Vet J | 2016 Jul | 27349882 |
| Antibiotic susceptibility profiles of Mycoplasma sp. 1220 strains isolated fromgeese in Hungary. | BMC Vet Res | 2016 Aug 19 | 27543140 |
| Short communication: In vitro antimicrobial susceptibility of Mycoplasma bovisisolates identified in milk from dairy cattle in Belgium, Germany, and Italy. | J Dairy Sci | 2016 Aug | 27209138 |
| Randomized, non-inferiority trial comparing a nitric oxide releasing solutionwith a macrolide antibiotic for control of bovine respiratory disease in beeffeedlot calves at high-risk of developing respiratory tract disease. | Res Vet Sci | 2016 Apr | 27033936 |
| Evaluation and validation of a multi-residue method based on biochip technologyfor the simultaneous screening of six families of antibiotics in muscle andaquaculture products. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016 | 26612266 |
| High-throughput method for macrolides and lincosamides antibiotics residuesanalysis in milk and muscle using a simple liquid-liquid extraction technique andliquid chromatography-electrospray-tandem mass spectrometry analysis (LC-MS/MS). | Talanta | 2015 Nov 1 | 26452878 |
| Antibiotic residue monitoring results for pork, chicken, and beef samples inVietnam in 2012-2013. | J Agric Food Chem | 2015 Jun 3 | 25601049 |
| [Antimicrobial susceptibility of Salmonella enterica isolated during thepre-harvest period in swine in Colombia]. | Rev Salud Publica (Bogota) | 2015 Jan-Feb | 26437705 |
| Antimicrobial susceptibility of Histophilus somni isolated from clinicallyaffected cattle in Australia. | Vet J | 2015 Feb | 25592262 |
| Variation in the Antimicrobial Susceptibility of Actinobacillus pleuropneumoniae Isolates in a Pig, Within a Batch of Pigs, and Among Batches of Pigs from OneFarm. | Microb Drug Resist | 2015 Aug | 25710484 |