Sarafloxacin
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Basic Info
| Common Name | Sarafloxacin(F05929) |
| 2D Structure | |
| FRCD ID | F05929 |
| CAS Number | 98105-99-8 |
| PubChem CID | 56208 |
| Formula | C20H17F2N3O3 |
| IUPAC Name | 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid |
| InChI Key | XBHBWNFJWIASRO-UHFFFAOYSA-N |
| InChI | InChI=1S/C20H17F2N3O3/c21-12-1-3-13(4-2-12)25-11-15(20(27)28)19(26)14-9-16(22)18(10-17(14)25)24-7-5-23-6-8-24/h1-4,9-11,23H,5-8H2,(H,27,28) |
| Canonical SMILES | C1CN(CCN1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)C4=CC=C(C=C4)F)F |
| Isomeric SMILES | C1CN(CCN1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)C4=CC=C(C=C4)F)F |
| Synonyms |
6-fluoro-1-(4-fluorophenyl)-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
Sarafloxacin
98105-99-8
Difloxacine
Difloxacino
Difloxacinum
Sarafloxacine
Sarafloxacino
Sarafloxacinum
Sarafloxacin [INN:BAN]
|
| Classifies |
Veterinary Drug
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Quinolines and derivatives |
| Subclass | Phenylquinolines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenylquinolines |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Phenylquinoline - Quinoline-3-carboxylic acid - Fluoroquinolone - N-arylpiperazine - Aminoquinoline - Haloquinoline - Dihydroquinolone - Dihydroquinoline - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Dialkylarylamine - Tertiary aliphatic/aromatic amine - Fluorobenzene - Halobenzene - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - 1,4-diazinane - Piperazine - Pyridine - Benzenoid - Heteroaromatic compound - Vinylogous amide - Tertiary amine - Amino acid or derivatives - Amino acid - Secondary amine - Azacycle - Carboxylic acid derivative - Carboxylic acid - Secondary aliphatic amine - Monocarboxylic acid or derivatives - Organofluoride - Organonitrogen compound - Organic nitrogen compound - Amine - Organic oxygen compound - Organopnictogen compound - Organic oxide - Organohalogen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 385.371 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 3 |
| Complexity | 645 |
| Monoisotopic Mass | 385.124 |
| Exact Mass | 385.124 |
| XLogP | 0.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 28 |
| 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- | 0.9569 |
| Human Intestinal Absorption | HIA+ | 0.9796 |
| Caco-2 Permeability | Caco2- | 0.8888 |
| P-glycoprotein Substrate | Substrate | 0.7727 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8769 |
| Non-inhibitor | 0.8725 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7091 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4421 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8603 |
| CYP450 2D6 Substrate | Non-substrate | 0.9053 |
| CYP450 3A4 Substrate | Non-substrate | 0.7649 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8057 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9273 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9293 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9067 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8865 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5978 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7924 |
| Non-inhibitor | 0.6183 | |
| AMES Toxicity | AMES toxic | 0.8295 |
| Carcinogens | Non-carcinogens | 0.8447 |
| Fish Toxicity | High FHMT | 0.9937 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8144 |
| Honey Bee Toxicity | Low HBT | 0.8952 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7658 |
| Carcinogenicity (Three-class) | Non-required | 0.6225 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4685 | LogS |
| Caco-2 Permeability | 0.7078 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1369 | LD50, mol/kg |
| Fish Toxicity | 1.3468 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5267 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Salmoniformes | Japan | 0.03ppm | |||
| Turkey,Edible Offal | Japan | 0.08ppm | |||
| Chicken,Edible Offal | Japan | 0.08ppm | |||
| Turkey,Kidney | Japan | 0.08ppm | |||
| Chicken,Kidney | Japan | 0.08ppm | |||
| Turkey,Liver | Japan | 0.08ppm | |||
| Chicken,Liver | Japan | 0.08ppm | |||
| Turkey,Fat | Japan | 0.02ppm | |||
| Chicken,Fat | Japan | 0.02ppm | |||
| Turkey,Muscle | Japan | 0.01ppm | |||
| Chicken,Muscle | Japan | 0.01ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Simultaneous determination of chlortetracycline, ampicillin and sarafloxacin inmilk using capillary electrophoresis with electrochemiluminescence detection. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2017Jan | 27805474 |
| Effect of various storage conditions on the stability of quinolones in raw milk. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016Jul | 27258809 |
| Electrical field assisted matrix solid phase dispersion as a powerful tool toimprove the extraction efficiency and clean-up of fluoroquinolones in bovinemilk. | J Chromatogr A | 2016 Aug 26 | 27492598 |
| Environmental and human health risks of antimicrobials used in Fenneropenaeuschinensis aquaculture production in China. | Environ Sci Pollut Res Int | 2016 Aug | 27137193 |
| Antibiotics and sweeteners in the aquatic environment: biodegradability,formation of phototransformation products, and in vitro toxicity. | Environ Sci Pollut Res Int | 2015 Nov | 26169816 |
| Multiresidue determination of fluoroquinolones in poultry muscle and kidneyaccording to the regulation 2002/657/EC. A systematic comparison of two differentapproaches: Liquid chromatography coupled to high-resolution mass spectrometry ortandem mass spectrometry. | J Chromatogr A | 2015 Jan 30 | 25577647 |
| Development of an immunochromatographic strip test for rapid detection ofciprofloxacin in milk samples. | Sensors (Basel) | 2014 Sep 10 | 25211194 |
| Development of a novel genetically modified bioluminescent-bacteria-based assayfor detection of fluoroquinolones in animal-derived foods. | Anal Bioanal Chem | 2014 Dec | 25354889 |
| Synthesis of novel haptens against ciprofloxacin and production of genericmonoclonal antibodies for immunoscreening of fluoroquinolones in meat. | J Sci Food Agric | 2013 Apr | 23044785 |
| Production of the broad specific monoclonal antibody against sarafloxacin forrapid immunoscreening of 12 fluoroquinolones in meat. | J Environ Sci Health B | 2013 | 23305282 |
| Determination of (fluoro)quinolones in eggs by liquid chromatography withfluorescence detection and confirmation by liquid chromatography-tandem massspectrometry. | Food Chem | 2012 Nov 15 | 22868110 |
| A sensitive chromatographic strip test for the rapid detection of enrofloxacin inchicken muscle. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2012 | 22243423 |
| Rapid screening method for quinolone residues in livestock and fishery productsusing immobilised metal chelate affinity chromatographic clean-up and liquidchromatography-fluorescence detection. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2011Sep | 21749230 |
| Determination of quinolone residues in infant and young children powdered milkcombining solid-phase extraction and ultra-performance liquidchromatography-tandem mass spectrometry. | J Chromatogr A | 2011 Oct 21 | 21683365 |
| Development of a quantitative multiclass/multiresidue method for 21 veterinarydrugs in shrimp. | J AOAC Int | 2011 Mar-Apr | 21563672 |
| Bufferized solvent extraction and HPLC fluorometric detection method forsarafloxacin in pig and chicken muscles. | Biomed Chromatogr | 2011 Mar | 20602509 |
| Determination of residual fluoroquinolones in honey by liquid chromatographyusing metal chelate affinity chromatography. | J AOAC Int | 2011 Jul-Aug | 21919363 |
| Comparison of different sample treatments for the analysis of quinolones in milk by capillary-liquid chromatography with laser induced fluorescence detection. | J Chromatogr A | 2011 Jul 29 | 21255783 |
| Plasma disposition and tissue depletion of difloxacin and its metabolitesarafloxacin in the food producing animals, chickens for fattening. | Food Chem Toxicol | 2011 Feb | 21108984 |
| Rapid determination of fluoroquinolone residues in honey by a microbiologicalscreening method and liquid chromatography. | J AOAC Int | 2010 Jul-Aug | 20922969 |