Enrofloxacin
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Basic Info
| Common Name | Enrofloxacin(F05808) |
| 2D Structure | |
| FRCD ID | F05808 |
| CAS Number | 93106-60-6 |
| PubChem CID | 71188 |
| Formula | C19H22FN3O3 |
| IUPAC Name | 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid |
| InChI Key | SPFYMRJSYKOXGV-UHFFFAOYSA-N |
| InChI | InChI=1S/C19H22FN3O3/c1-2-21-5-7-22(8-6-21)17-10-16-13(9-15(17)20)18(24)14(19(25)26)11-23(16)12-3-4-12/h9-12H,2-8H2,1H3,(H,25,26) |
| Canonical SMILES | CCN1CCN(CC1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)C4CC4)F |
| Isomeric SMILES | CCN1CCN(CC1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)C4CC4)F |
| Synonyms |
CFPQ
Bay-Vp-2674
Enrofloxacin
93106-60-6
Baytril
Enrofloxacine
Enrofloxacino
Enrofloxacinum
endrofloxicin
BAY VP 2674
|
| Classifies |
Veterinary Drug
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Quinolines and derivatives |
| Subclass | Quinoline carboxylic acids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Quinoline carboxylic acids |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Quinoline-3-carboxylic acid - Fluoroquinolone - N-arylpiperazine - Aminoquinoline - Haloquinoline - Dihydroquinolone - Dihydroquinoline - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Dialkylarylamine - Tertiary aliphatic/aromatic amine - N-alkylpiperazine - Benzenoid - Pyridine - Aryl fluoride - Piperazine - Aryl halide - 1,4-diazinane - Vinylogous amide - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Amino acid - Amino acid or derivatives - Azacycle - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organooxygen compound - Amine - Organic oxide - Organohalogen compound - Organofluoride - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 359.401 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 4 |
| Complexity | 613 |
| Monoisotopic Mass | 359.165 |
| Exact Mass | 359.165 |
| XLogP | -0.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 26 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9490 |
| Human Intestinal Absorption | HIA+ | 0.9919 |
| Caco-2 Permeability | Caco2+ | 0.7513 |
| P-glycoprotein Substrate | Substrate | 0.8137 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7791 |
| Non-inhibitor | 0.8534 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.6647 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4936 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8217 |
| CYP450 2D6 Substrate | Non-substrate | 0.8575 |
| CYP450 3A4 Substrate | Non-substrate | 0.7024 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9189 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8878 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8643 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8427 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8899 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5197 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7880 |
| Non-inhibitor | 0.7518 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.8649 |
| Fish Toxicity | High FHMT | 0.9979 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9594 |
| Honey Bee Toxicity | Low HBT | 0.8959 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.8000 |
| Carcinogenicity (Three-class) | Non-required | 0.5950 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.9280 | LogS |
| Caco-2 Permeability | 1.0744 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8878 | LD50, mol/kg |
| Fish Toxicity | 1.1060 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6797 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Poultry Animals,Edible Offal | Japan | 0.1ppm | |||
| Chicken,Edible Offal | Japan | 0.1ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.1ppm | |||
| Chicken,Kidney | Japan | 0.1ppm | |||
| Other Poultry Animals,Liver | Japan | 0.1ppm | |||
| Chicken,Liver | Japan | 0.1ppm | |||
| Other Poultry Animals,Fat | Japan | 0.05ppm | |||
| Chicken,Fat | Japan | 0.05ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.05ppm | |||
| Chicken,Muscle | Japan | 0.05ppm | |||
| Milk | Japan | 0.05ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.05ppm | |||
| Pig,Edible Offal | Japan | 0.05ppm | |||
| Cattle,Edible Offal | Japan | 0.05ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.1ppm | |||
| Pig,Kidney | Japan | 0.1ppm | |||
| Cattle,Kidney | Japan | 0.1ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 0.1ppm | |||
| Pig,Liver | Japan | 0.1ppm | |||
| Cattle,Liver | Japan | 0.1ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| High occurrence rates of enrofloxacin and ciprofloxacin residues in retailpoultry meat revealed by an ultra-sensitive mass-spectrometric method, andantimicrobial resistance to fluoroquinolones in Campylobacter spp. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018Jun | 29377766 |
| Prevalence, bioserotyping and antibiotic resistance of pathogenic Yersiniaenterocolitica detected in pigs at slaughter in Sardinia. | Int J Food Microbiol | 2018 Oct 20 | 29929063 |
| Therapeutic administration of enrofloxacin in mice does not select forfluoroquinolone resistance in Campylobacter jejuni. | Can J Microbiol | 2018 May 11:1-14 | 29750889 |
| Presence of antibiotic residues in various environmental compartments of Shandongprovince in eastern China: Its potential for resistance development andecological and human risk. | Environ Int | 2018 May | 29501851 |
| Antibiotic susceptibilities of livestock isolates of leptospira. | Int J Antimicrob Agents | 2018 May | 29305960 |
| Prevalence of most common human pathogenic Campylobacter spp. in dogs and cats inStyria, Austria. | Vet Med Sci | 2018 May | 29851311 |
| Consumption of antibacterial molecules in broiler production in Morocco. | Vet Med Sci | 2018 May | 29851315 |
| Use of quercetin in animal feed: effects on the P-gp expression andpharmacokinetics of orally administrated enrofloxacin in chicken. | Sci Rep | 2018 Mar 13 | 29535328 |
| Hexafluoroisopropanol-induced salt-free catanionic surfactant coacervateextraction method for determination of fluoroquinolones in milk samples. | Food Chem | 2018 Mar 1 | 29037667 |
| Occurrence and risk assessment of fluoroquinolones and tetracyclines in cultured fish from a coastal region of northern China. | Environ Sci Pollut Res Int | 2018 Mar | 29305805 |
| Efficacy of a one-shot marbofloxacin treatment on acute pleuropneumonia afterexperimental aerosol inoculation of nursery pigs. | Porcine Health Manag | 2018 Jun 22 | 29977591 |
| Sample preparation combined with electroanalysis to improve simultaneousdetermination of antibiotics in animal derived food samples. | Food Chem | 2018 Jun 1 | 29412930 |
| 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 Toxicol | 2018 Jun | 29725709 |
| Prevalence and Antimicrobial Resistance Profile of Listeria Species Isolated fromFarmed and On-Sale Rainbow Trout ( Oncorhynchus mykiss) in Western Iran. | J Food Prot | 2018 Jun | 29714625 |
| Effect of copper on the accumulation and elimination kinetics of fluoroquinolonesin the zebrafish (Danio rerio). | Ecotoxicol Environ Saf | 2018 Jul 30 | 29549736 |
| Antimicrobial resistance trends in Escherichia coli isolated from diseasedfood-producing animals in France: A 14-year period time-series study. | Zoonoses Public Health | 2018 Feb | 29110404 |
| Quantitative prevalence and characterization of Campylobacter from chicken andduck carcasses from poultry slaughterhouses in South Korea. | Poult Sci | 2018 Aug 1 | 29757448 |
| Quinolones and tetracyclines in aquaculture fish by a simple and rapid LC-MS/MSmethod. | Food Chem | 2018 Apr 15 | 29287347 |
| Salmonella isolated from chicken carcasses from a slaughterhouse in the state of Mato Grosso, Brazil: antibiotic resistance profile, serotyping, andcharacterization by repetitive sequence-based PCR system. | Poult Sci | 2018 Apr 1 | 29365208 |
| Analysis of veterinary drug residue monitoring results for commercial livestockproducts in Taiwan between 2011 and 2015. | J Food Drug Anal | 2018 Apr | 29567225 |