Doxycycline

Basic Info

Common NameDoxycycline(F05884)
2D Structure
FRCD IDF05884
CAS Number564-25-0
PubChem CID54671203
FormulaC22H24N2O8
IUPAC Name

(4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide

InChI Key

SGKRLCUYIXIAHR-AKNGSSGZSA-N

InChI

InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1

Canonical SMILES

CC1C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O

Isomeric SMILES

C[C@@H]1[C@H]2[C@@H]([C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O

Synonyms
        
            doxycycline
        
            Vibramycin
        
            564-25-0
        
            Doxytetracycline
        
            Doxiciclina
        
            Doxycyclinum
        
            Monodox
        
            Oracea
        
            Vibra-tabs
        
            Doxy-Caps
Classifies
                

                  
                    Predicted: 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-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Cyclohexenone - Aralkylamine - Benzenoid - Cyclic alcohol - Tertiary alcohol - Vinylogous acid - Cyclic ketone - Tertiary aliphatic amine - Tertiary amine - Secondary alcohol - Ketone - Carboximidic acid - Carboximidic acid derivative - Polyol - Enol - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Alcohol - Amine - Organopnictogen compound - Carbonyl group - Organic oxide - 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 Weight444.44
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count2
Complexity956
Monoisotopic Mass444.153
Exact Mass444.153
XLogP-0.7
Formal Charge0
Heavy Atom Count32
Defined Atom Stereocenter Count6
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-0.9881
Human Intestinal AbsorptionHIA+0.8500
Caco-2 PermeabilityCaco2-0.8706
P-glycoprotein SubstrateSubstrate0.6990
P-glycoprotein InhibitorNon-inhibitor0.8038
Non-inhibitor0.8628
Renal Organic Cation TransporterNon-inhibitor0.9562
Distribution
Subcellular localizationMitochondria0.7882
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8008
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateSubstrate0.6551
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9144
CYP450 2D6 InhibitorNon-inhibitor0.9293
CYP450 2C19 InhibitorNon-inhibitor0.9099
CYP450 3A4 InhibitorNon-inhibitor0.8567
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8086
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9946
Non-inhibitor0.7466
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.8632
Fish ToxicityHigh FHMT0.9608
Tetrahymena Pyriformis ToxicityHigh TPT0.9489
Honey Bee ToxicityLow HBT0.6149
BiodegradationNot ready biodegradable0.9941
Acute Oral ToxicityIII0.7981
Carcinogenicity (Three-class)Non-required0.7022
Model Value Unit
Absorption
Aqueous solubility-3.0711LogS
Caco-2 Permeability0.5625LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.3159LD50, mol/kg
Fish Toxicity0.5953pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5989pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
PerciformesJapan0.05ppm
Other Poultry Animals,Edible OffalJapan0.3ppm
Chicken,Edible OffalJapan0.05ppm
Other Poultry Animals,KidneyJapan0.6ppm
Chicken,KidneyJapan0.05ppm
Other Poultry Animals,LiverJapan0.3ppm
Chicken,LiverJapan0.05ppm
Other Poultry Animals,FatJapan0.3ppm
Chicken,FatJapan0.05ppm
Other Poultry Animals,MuscleJapan0.1ppm
Chicken,MuscleJapan0.05ppm
Pig,Edible OffalJapan0.05ppm
Cattle,Edible OffalJapan0.3ppm
Pig,KidneyJapan0.05ppm
Cattle,KidneyJapan0.6ppm
Pig,LiverJapan0.05ppm
Cattle,LiverJapan0.3ppm
Pig,FatJapan0.05ppm
Cattle,FatJapan0.1ppm
Pig,MuscleJapan0.05ppm

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
In vitro model to assess the adsorption of oral veterinary drugs to mycotoxin binders in a feed- and aflatoxin B1-containing buffered matrix.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2018 Sep30016205
A multifunctional molecularly imprinted polymer-based biosensor for directdetection of doxycycline in food samples.Talanta2018 May 1529501183
Presence of antibiotic residues in various environmental compartments of Shandongprovince in eastern China: Its potential for resistance development andecological and human risk.Environ Int2018 May29501851
Antibiotic susceptibilities of livestock isolates of leptospira.Int J Antimicrob Agents2018 May29305960
Characterization of multiple antibiotic resistance of culturable microorganismsand metagenomic analysis of total microbial diversity of marine fish sold inretail shops in Mumbai, India.Environ Sci Pollut Res Int2018 Mar29243150
Using the lentiviral vector system to stably express chicken P-gp and BCRP inMDCK cells for screening the substrates and studying the interplay of bothtransporters.Arch Toxicol2018 Jun29725709
A design of experiment approach for efficient multi-parametric drug testing usinga Caenorhabditis elegans model.Integr Biol (Camb)2018 Jan 2229333560
Targeting mutant KRAS with CRISPR-Cas9 controls tumor growth.Genome Res2018 Jan 1129326299
Chlortetracycline and related tetracyclines: detection in wheat and rye grain.J Sci Food Agric2018 Feb 2729484666
Soil texture-depending effects of doxycycline and streptomycin applied withmanure on the bacterial community composition and resistome.FEMS Microbiol Ecol2018 Feb 129087461
Antibiotic Resistance Genes and Antibiotic Susceptibility of Oral Enterococcusfaecalis Isolates Compared to Isolates from Hospitalized Patients and Food.Adv Exp Med Biol201828601926
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
Characterization and zoonotic impact of Shiga toxin producing <i>Escherichia coli</i> in some wild bird species.Vet World2017 Sep29062203
Chemical, microbial and antibiotic susceptibility analyses of groundwater after amajor flood event in Chennai.Sci Data2017 Oct 1028994821
Effects of ultrasound irradiation on enzymatic hydrolysis of protein andapplication for the determination of tetracyclines in complex matrices.Drug Test Anal2017 Oct28262009
Clinical benefits of incorporating doxycycline into a canine heartworm treatment protocol.Parasit Vectors2017 Nov 929143657
Efficacy of Ceftriaxone, Cefepime, Doxycycline, Ciprofloxacin, and CombinationTherapy for Vibrio vulnificus Foodborne Septicemia.Antimicrob Agents Chemother2017 Nov 2228971862
Salting-out-enhanced ionic liquid microextraction with a dual-role solvent forsimultaneous determination of trace pollutants with a wide polarity range inaqueous samples.Anal Bioanal Chem2017 Nov28871466
Antimicrobial susceptibility and genetic characterization of Escherichia colirecovered from frozen game meat.Food Microbiol2017 May28040165