Chlortetracycline

Basic Info

Common NameChlortetracycline(F05698)
2D Structure
FRCD IDF05698
CAS Number57-62-5
PubChem CID54675777
FormulaC22H23ClN2O8
IUPAC Name

(4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide

InChI Key

DHPRQBPJLMKORJ-XRNKAMNCSA-N

InChI

InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26-27,30,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1

Canonical SMILES

CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O

Isomeric SMILES

C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O

Synonyms
        
            chlorocyclinum
        
            chlortetracycline
        
            AUREOMYCIN
        
            Clortetraciclina
        
            Chlortetracyclinum
        
            7-Chlorotetracycline
        
            57-62-5
        
            UNII-WCK1KIQ23Q
        
            Chlorotetracycline
        
            WCK1KIQ23Q
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassTetracyclines
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentTetracyclines
Alternative Parents
Molecular FrameworkAromatic homopolycyclic compounds
SubstituentsTetracycline - 1-naphthol - Naphthalene - 1-hydroxy-2-unsubstituted benzenoid - Cyclohexenone - Aralkylamine - Aryl chloride - Aryl halide - Benzenoid - Cyclic alcohol - Tertiary alcohol - Vinylogous acid - Cyclic ketone - Tertiary amine - Tertiary aliphatic amine - Ketone - Polyol - Carboximidic acid - Carboximidic acid derivative - Enol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organohalogen compound - Organochloride - Alcohol - Organonitrogen compound - Organooxygen compound - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Amine - Aromatic homopolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.

Properties

Property NameProperty Value
Molecular Weight478.882
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count2
Complexity1010
Monoisotopic Mass478.114
Exact Mass478.114
XLogP-1.3
Formal Charge0
Heavy Atom Count33
Defined Atom Stereocenter Count5
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-0.9707
Human Intestinal AbsorptionHIA+0.8224
Caco-2 PermeabilityCaco2+0.6302
P-glycoprotein SubstrateSubstrate0.7841
P-glycoprotein InhibitorNon-inhibitor0.8316
Non-inhibitor0.7581
Renal Organic Cation TransporterNon-inhibitor0.9376
Distribution
Subcellular localizationMitochondria0.7786
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7968
CYP450 2D6 SubstrateNon-substrate0.8771
CYP450 3A4 SubstrateSubstrate0.6961
CYP450 1A2 InhibitorNon-inhibitor0.9046
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8734
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5745
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9956
Non-inhibitor0.6021
AMES ToxicityNon AMES toxic0.8911
CarcinogensNon-carcinogens0.9182
Fish ToxicityHigh FHMT0.9938
Tetrahymena Pyriformis ToxicityHigh TPT0.9846
Honey Bee ToxicityLow HBT0.6779
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.5284
Carcinogenicity (Three-class)Non-required0.6484
Model Value Unit
Absorption
Aqueous solubility-2.9039LogS
Caco-2 Permeability0.7737LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1711LD50, mol/kg
Fish Toxicity0.8042pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6815pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
EggsUnited States0.4ppm
Kidney Of DucksUnited States12ppm
Kidney Of SheepUnited States12ppm
Kidney Of SwineUnited States12ppm
Kidney Of CalvesUnited States12ppm
Kidney Of Nonlactating Dairy CowsUnited States12ppm
Kidney Of Beef CattleUnited States12ppm
Fat Of DucksUnited States12ppm
Fat Of TurkeysUnited States12ppm
Fat Of ChickensUnited States12ppm
Fat Of SheepUnited States12ppm
Fat Of SwineUnited States12ppm
Fat Of CalvesUnited States12ppm
Fat Of Nonlactating Dairy CowsUnited States12ppm
Fat Of Beef CattleUnited States12ppm
Muscle Of DucksUnited States2ppm
Muscle Of TurkeysUnited States2ppm
Muscle Of ChickensUnited States2ppm
Muscle Of SheepUnited States2ppm
Muscle Of SwineUnited States2ppm

References

TitleJournalDatePubmed ID
Tetracycline antibiotics transfer from contaminated milk to dairy products andthe effect of the skimming step and pasteurisation process on residueconcentrations.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2018Jan29076394
Reprint of: Quantitative proteomic analysis reveals that chemotaxis is involvedin chlortetracycline resistance of Aeromonas hydrophila.J Proteomics2018 May 3029604439
Chlortetracycline and florfenicol induce expression of genes associated withpathogenicity in multidrug-resistant Salmonella enterica serovar Typhimurium.Gut Pathog2018 Mar 529515658
Effects of Ceftiofur and Chlortetracycline on the Resistomes of Feedlot Cattle.Appl Environ Microbiol2018 Jun 1829728379
Chlortetracycline and related tetracyclines: detection in wheat and rye grain.J Sci Food Agric2018 Feb 2729484666
Quantitative proteomic analysis reveals that chemotaxis is involved inchlortetracycline resistance of Aeromonas hydrophila.J Proteomics2018 Feb 1028986269
A new approach for the extraction of tetracyclines from soil matrices:application of the microwave-extraction technique.Anal Bioanal Chem2018 Feb29350257
Visual and fluorometric lateral flow immunoassay combined with a dual-functional test mode for rapid determination of tetracycline antibiotics.Mikrochim Acta2018 Aug 730088104
Qualitative and quantitative drug residue analyses: Chlortetracycline inwhite-tailed deer (Odocoileus virginianus) and supermarket meat by liquidchromatography tandem-mass spectrometry.J Chromatogr B Analyt Technol Biomed Life Sci2018 Aug 1529913335
Long-Term Exposure of Agricultural Soil to Veterinary Antibiotics Changes thePopulation Structure of Symbiotic Nitrogen-Fixing Rhizobacteria Occupying Nodulesof Soybeans (Glycine max).Appl Environ Microbiol2018 Apr 1629500255
Effect of composting and soil type on dissipation of veterinary antibiotics inland-applied manures.Chemosphere2018 Apr29306199
Development and validation of multi-residue analysis for tetracycline antibioticsin feed by high performance liquid chromatography coupled to mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017Sep28795656
Simultaneous determination of chlortetracycline, ampicillin and sarafloxacin inmilk using capillary electrophoresis with electrochemiluminescence detection.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017Jan27805474
Population dynamics of enteric Salmonella in response to antimicrobial use inbeef feedlot cattle.Sci Rep2017 Oct 3029085049
Effect of antimicrobials administered via liquid feed on the occurrence ofsulphonamide and trimethoprim resistant Enterobacteriaceae: case-control study.Porcine Health Manag2017 Oct 329026638
Genotypic and epidemiologic characterization of extended-spectrum cephalosporinresistant Salmonella enterica from US beef feedlots.Prev Vet Med2017 Oct 128992919
Effects of ultrasound irradiation on enzymatic hydrolysis of protein andapplication for the determination of tetracyclines in complex matrices.Drug Test Anal2017 Oct28262009
Models of antimicrobial pressure on intestinal bacteria of the treated hostpopulations.Epidemiol Infect2017 Jul28462738
Feed Supplementation with Red Seaweeds, Chondrus crispus and Sarcodiothecagaudichaudii, Reduce Salmonella Enteritidis in Laying Hens.Front Microbiol2017 Apr 1028443073
Effect of Vancomycin, Tylosin, and Chlortetracycline on Vancomycin-ResistantEnterococcus faecium Colonization of Broiler Chickens During Grow-Out.Foodborne Pathog Dis2017 Apr28128649