Basic Info

Common NameTilmicosin(F06169)
2D Structure
FRCD IDF06169
CAS Number108050-54-0
PubChem CID5282521
FormulaC46H80N2O13
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 DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesAminosaccharides
Direct ParentAminoglycosides
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsAminoglycoside 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
DescriptionThis 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 NameProperty Value
Molecular Weight869.147
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count15
Rotatable Bond Count12
Complexity1420
Monoisotopic Mass868.566
Exact Mass868.566
XLogP3.6
Formal Charge0
Heavy Atom Count61
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9823
Human Intestinal AbsorptionHIA-0.6896
Caco-2 PermeabilityCaco2-0.6082
P-glycoprotein SubstrateSubstrate0.9020
P-glycoprotein InhibitorInhibitor0.9362
Inhibitor0.8105
Renal Organic Cation TransporterNon-inhibitor0.7977
Distribution
Subcellular localizationMitochondria0.6053
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8663
CYP450 2D6 SubstrateNon-substrate0.8822
CYP450 3A4 SubstrateSubstrate0.6459
CYP450 1A2 InhibitorNon-inhibitor0.9020
CYP450 2C9 InhibitorNon-inhibitor0.9147
CYP450 2D6 InhibitorNon-inhibitor0.8908
CYP450 2C19 InhibitorNon-inhibitor0.8797
CYP450 3A4 InhibitorNon-inhibitor0.9215
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9815
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8220
Non-inhibitor0.6280
AMES ToxicityNon AMES toxic0.7446
CarcinogensNon-carcinogens0.9339
Fish ToxicityHigh FHMT0.9053
Tetrahymena Pyriformis ToxicityHigh TPT0.9875
Honey Bee ToxicityLow HBT0.6017
BiodegradationNot ready biodegradable0.6247
Acute Oral ToxicityIII0.7234
Carcinogenicity (Three-class)Non-required0.4812

Model Value Unit
Absorption
Aqueous solubility-2.4613LogS
Caco-2 Permeability0.3766LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5426LD50, mol/kg
Fish Toxicity1.4340pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5720pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Aquatic AnimalJapan0.05ppm
CrustaceansJapan0.05ppm
Shelled MolluscasJapan0.05ppm
Other FishJapan0.05ppm
PerciformesJapan0.05ppm
AnguilliformesJapan0.05ppm
SalmoniformesJapan0.05ppm
Other Poultry Animals,Edible OffalJapan0.3ppm
Chicken,Edible OffalJapan0.3ppm
Other Poultry Animals,KidneyJapan0.3ppm
Chicken,KidneyJapan0.3ppm
Other Poultry Animals,LiverJapan1ppm
Chicken,LiverJapan1ppm
Other Poultry Animals,FatJapan0.08ppm
Chicken,FatJapan0.08ppm
Other Poultry Animals,MuscleJapan0.08ppm
Chicken,MuscleJapan0.08ppm
Other Terrestrial Mammals,Edible OffalJapan1ppm
Sheep,Edible OffalJapan0.3ppm
Pig,Edible OffalJapan1ppm

References

TitleJournalDatePubmed ID
Noncovalent Interaction of Tilmicosin with Bovine Serum Albumin.Molecules2018 Jul 3130065238
Prevalence and Characterization of <i>Staphylococcus aureus</i> Cultured From Raw Milk Taken From Dairy Cows With Mastitis in Beijing, China.Front Microbiol201829988423
Antibiofilm and antibacterial effects of specific chitosan molecules onStaphylococcus aureus isolates associated with bovine mastitis.PLoS One2017 May 928486482
Detection of antibiotics in chicken eggs obtained from supermarkets in Ho ChiMinh City, Vietnam.J Environ Sci Health B2017 Jun 328281880
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 Immunol2017 Jun28504455
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 Sci2017 Dec28231472
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 Assess2016Jul27189753
Whole Genome Sequence Analysis of Pig Respiratory Bacterial Pathogens withElevated Minimum Inhibitory Concentrations for Macrolides.Microb Drug Resist2016 Oct26981707
Separation analysis of macrolide antibiotics with good performance on apositively charged C18HCE column.J Sep Sci2016 Mar26782089
Antimicrobial susceptibility of Mycoplasma bovis isolates from veal calves anddairy cattle in the Netherlands.Vet Microbiol2016 Jun 3027259820
Antimicrobial resistance genes in Actinobacillus pleuropneumoniae, Haemophilusparasuis and Pasteurella multocida isolated from Australian pigs.Aust Vet J2016 Jul27349882
Antibiotic susceptibility profiles of Mycoplasma sp. 1220 strains isolated fromgeese in Hungary.BMC Vet Res2016 Aug 1927543140
Short communication: In vitro antimicrobial susceptibility of Mycoplasma bovisisolates identified in milk from dairy cattle in Belgium, Germany, and Italy.J Dairy Sci2016 Aug27209138
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 Sci2016 Apr27033936
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 Assess201626612266
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).Talanta2015 Nov 126452878
Antibiotic residue monitoring results for pork, chicken, and beef samples inVietnam in 2012-2013.J Agric Food Chem2015 Jun 325601049
[Antimicrobial susceptibility of Salmonella enterica isolated during thepre-harvest period in swine in Colombia].Rev Salud Publica (Bogota)2015 Jan-Feb26437705
Antimicrobial susceptibility of Histophilus somni isolated from clinicallyaffected cattle in Australia.Vet J2015 Feb25592262
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 Resist2015 Aug25710484