Basic Info

Common NameTulathromycin(F06197)
2D Structure
FRCD IDF06197
CAS Number217500-96-4
PubChem CID9832301
FormulaC41H79N3O12
IUPAC Name

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-5-(propylaminomethyl)oxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one

InChI Key

GUARTUJKFNAVIK-QPTWMBCESA-N

InChI

InChI=1S/C41H79N3O12/c1-15-17-42-22-41(50)28(8)53-31(20-39(41,10)51-14)55-33-25(5)35(56-37-32(45)29(44(12)13)18-24(4)52-37)38(9,48)19-23(3)21-43-27(7)34(46)40(11,49)30(16-2)54-36(47)26(33)6/h23-35,37,42-43,45-46,48-50H,15-22H2,1-14H3/t23-,24-,25+,26-,27-,28+,29+,30-,31+,32-,33+,34-,35-,37+,38-,39-,40-,41+/m1/s1

Canonical SMILES

CCCNCC1(C(OC(CC1(C)OC)OC2C(C(C(CC(CNC(C(C(C(OC(=O)C2C)CC)(C)O)O)C)C)(C)O)OC3C(C(CC(O3)C)N(C)C)O)C)C)O

Isomeric SMILES

CCCNC[C@@]1([C@@H](O[C@H](C[C@@]1(C)OC)O[C@H]2[C@@H]([C@H]([C@](C[C@H](CN[C@@H]([C@H]([C@]([C@H](OC(=O)[C@@H]2C)CC)(C)O)O)C)C)(C)O)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)C)C)O

Synonyms
        
            UNII-897A3KN7AP
        
            DTXSID60274184
        
            Tulathromycin A
        
            Tulathromycin
        
            217500-96-4
        
            Draxxin
        
            897A3KN7AP
        
            Tulathrmycin A
        
            Tulathromycin A [USAN]
        
            SCHEMBL14672085
        
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 - Monosaccharide - Oxane - Tertiary alcohol - 1,2-aminoalcohol - Amino acid or derivatives - Carboxylic acid ester - Lactone - Secondary alcohol - Tertiary amine - Tertiary aliphatic amine - Acetal - Organoheterocyclic compound - Secondary amine - Polyol - Azacycle - Carboxylic acid derivative - Dialkyl ether - Secondary aliphatic amine - Ether - Oxacycle - Monocarboxylic acid or derivatives - Carbonyl group - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Alcohol - Hydrocarbon derivative - Amine - Organonitrogen compound - 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 Weight806.092
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count15
Rotatable Bond Count11
Complexity1240
Monoisotopic Mass805.566
Exact Mass805.566
XLogP3.8
Formal Charge0
Heavy Atom Count56
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9918
Human Intestinal AbsorptionHIA-0.7747
Caco-2 PermeabilityCaco2-0.7511
P-glycoprotein SubstrateSubstrate0.9265
P-glycoprotein InhibitorInhibitor0.7321
Non-inhibitor0.8213
Renal Organic Cation TransporterNon-inhibitor0.8779
Distribution
Subcellular localizationLysosome0.7983
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8384
CYP450 2D6 SubstrateNon-substrate0.8682
CYP450 3A4 SubstrateSubstrate0.6097
CYP450 1A2 InhibitorNon-inhibitor0.9537
CYP450 2C9 InhibitorNon-inhibitor0.8994
CYP450 2D6 InhibitorNon-inhibitor0.8934
CYP450 2C19 InhibitorNon-inhibitor0.9172
CYP450 3A4 InhibitorNon-inhibitor0.9486
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9858
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9695
Non-inhibitor0.5891
AMES ToxicityNon AMES toxic0.9024
CarcinogensNon-carcinogens0.9397
Fish ToxicityHigh FHMT0.6586
Tetrahymena Pyriformis ToxicityHigh TPT0.9494
Honey Bee ToxicityLow HBT0.6566
BiodegradationNot ready biodegradable0.9949
Acute Oral ToxicityIII0.6869
Carcinogenicity (Three-class)Non-required0.5899

Model Value Unit
Absorption
Aqueous solubility-1.9958LogS
Caco-2 Permeability0.0192LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5888LD50, mol/kg
Fish Toxicity1.8035pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2842pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Cattle,Edible OffalJapan3ppm
Pig,KidneyJapan9ppm
Cattle,KidneyJapan3ppm
Pig,FatJapan0.3ppm
Cattle,FatJapan0.2ppm
Pig,MuscleJapan2ppm
Cattle,MuscleJapan0.3ppm

References

TitleJournalDatePubmed ID
Injectable antimicrobials in commercial feedlot cattle and their effect on thenasopharyngeal microbiota and antimicrobial resistance.Vet Microbiol2018 Feb29408026
Prevalence and antimicrobial susceptibility of Mannheimia haemolytica,Pasteurella multocida, and Histophilus somni isolated from the lower respiratory tract of healthy feedlot cattle and those diagnosed with bovine respiratorydisease.Vet Microbiol2017 Sep28888626
Etiology of acute respiratory disease in fattening pigs in Finland.Porcine Health Manag2017 Aug 2328852568
Whole Genome Sequence Analysis of Pig Respiratory Bacterial Pathogens withElevated Minimum Inhibitory Concentrations for Macrolides.Microb Drug Resist2016 Oct26981707
Estimation of tulathromycin depletion in plasma and milk after subcutaneousinjection in lactating goats using a nonlinear mixed-effects pharmacokineticmodeling approach.BMC Vet Res2016 Nov 1827863483
Antimicrobial susceptibility of Mycoplasma bovis isolates from veal calves anddairy cattle in the Netherlands.Vet Microbiol2016 Jun 3027259820
Pharmacokinetics and lung and muscle concentrations of tulathromycin followingsubcutaneous administration in white-tailed deer (Odocoileus virginianus).J Vet Pharmacol Ther2016 Jun26669905
Antimicrobial resistance genes in Actinobacillus pleuropneumoniae, Haemophilusparasuis and Pasteurella multocida isolated from Australian pigs.Aust Vet J2016 Jul27349882
Development of Analytical Method and Monitoring of Veterinary Drug Residues inKorean Animal Products.Korean J Food Sci Anim Resour201627433102
Pharmacokinetics of tulathromycin after subcutaneous injection in North American bison (Bison bison).J Vet Pharmacol Ther2015 Oct25772094
Development and validation of determinative and confirmatory LC-MS/MSmethodologies for total florfenicol and tulathromycin residues in bovine, equine and porcine kidney, liver and muscle tissues.J Chromatogr B Analyt Technol Biomed Life Sci2015 Mar 125612770
Clinical evidence for individual animal therapy for papillomatous digitaldermatitis (hairy heel wart) and infectious bovine pododermatitis (foot rot).Vet Clin North Am Food Anim Pract2015 Mar25705026
Antimicrobial susceptibility of Histophilus somni isolated from clinicallyaffected cattle in Australia.Vet J2015 Feb25592262
Pharmacokinetics of tulathromycin in edible tissues of healthy and experimentallyinfected pigs with Actinobacillus pleuropneumoniae.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201526247868
Use of a proposed antimicrobial susceptibility testing method for Haemophilusparasuis.Vet Microbiol2014 Aug 2724984947
Pharmacokinetics of tulathromycin in plasma and milk samples after a singlesubcutaneous injection in lactating goats (Capra hircus).J Vet Pharmacol Ther2014 Apr23889045
Impact of health management, health treatments, and zilpaterol hydrochloridesupplementation on carcass quality, color, and palatability traits in heifers.J Anim Sci2013 Jul23658348
Estimating tulathromycin withdrawal time in pigs using a physiologically basedpharmacokinetics model.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201323767965
Pharmacokinetics and tissue elimination of tulathromycin following subcutaneousadministration in meat goats.Am J Vet Res2012 Oct23013191
Pharmacokinetics of tulathromycin and its metabolite in swine administered withan intravenous bolus injection and a single gavage.J Vet Pharmacol Ther2012 Jun21749408