SARAFLOXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H17F2N3O3
Molecular Weight	385.3641
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CN(C2=CC=C(F)C=C2)C3=CC(N4CCNCC4)=C(F)C=C3C1=O

InChI

InChIKey=XBHBWNFJWIASRO-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: http://adisinsight.springer.com/drugs/800000453 | http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015842.pdf

Sarafloxacin [A 55620] is a quinolone antibiotic that was under development with Abbott Laboratories in the USA. It was removed from clinical use by its manufacturer Abbott Laboratories from April 30, 2001. It was never approved for use in the US or Canada.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mycoplasma gallisepticum 2 Target ID: CHEMBL612643 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11417828	Inhibitor 8297
DNA gyrase 26 Target ID: CHEMBL2094139 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D08506 \| http://adisinsight.springer.com/drugs/800000453 \| http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015842.pdf	Inhibitor 8297
Enterobacteriaceae 2 Target ID: CHEMBL614436 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3208547	Inhibitor 8297
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3539011	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intestinal infections 2 Sources: http://adisinsight.springer.com/drugs/800000453 https://www.ncbi.nlm.nih.gov/pubmed/9791759	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Determination of 16 quinolone residues in animal tissues using high performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry].	2007 Jul	17970104
Development and validation of an HPLC confirmatory method for residue analysis of ten quinolones in tissues of various food-producing animals, according to the European Union Decision 2002/657/EC.	2007 Nov	17763524
Validation of an HPLC-UV method according to the European Union Decision 2002/657/EC for the simultaneous determination of 10 quinolones in chicken muscle and egg yolk.	2007 Nov 15	17977806
Multiresidue method for simultaneous determination of quinolone antibacterials in pig kidney samples by liquid chromatography with fluorescence detection.	2007 Nov 15	17951118
Multiresidue HPLC analysis of ten quinolones in milk after solid phase extraction: validation according to the European Union Decision 2002/657/EC.	2007 Oct	17683042
Ionic liquids as mobile phase additives for the high-performance liquid chromatographic analysis of fluoroquinolone antibiotics in water samples.	2008 Dec	18854988
Trace analysis of quinolone and fluoroquinolone antibiotics from wastewaters by liquid chromatography-electrospray tandem mass spectrometry.	2008 Dec 19	19007934
Development of an HPLC multi-residue method for the determination of ten quinolones in bovine liver and porcine kidney according to the European Union Decision 2002/657/EC.	2008 Jan	18081209
Multiresidue determination of quinolones in animal and fishery products by HPLC.	2008 Jun	18633210
Multiclass determination and confirmation of antibiotic residues in honey using LC-MS/MS.	2008 Mar 12	18257525
In-line solid-phase extraction preconcentration in capillary electrophoresis-tandem mass spectrometry for the multiresidue detection of quinolones in meat by pressurized liquid extraction.	2008 May	18409156
Endotoxemic pulmonary hypertension is largely mediated by endothelin-induced venous constriction.	2008 May	18214440
Simultaneous determination of quinolone antibacterials in bovine milk by liquid chromatography-mass spectrometry.	2008 Nov	18651586
Simultaneous determination of 13 quinolones in eggs using column high-performance liquid chromatography/electrospray ionization-tandem mass spectrometry and depletion of pefloxacin methanesulfonate in eggs.	2008 Nov-Dec	19202815
Solid-phase extraction of fluoroquinolones from aqueous samples using a water-compatible stochiometrically imprinted polymer.	2008 Oct 24	18790491
Development and validation of a solid-phase extraction method coupled to liquid chromatography with fluorescence detection for the determination of fluoroquinolone residues in powdered infant formulae. Application to the analysis of samples from the Spanish and Latin American market.	2008 Oct 31	18829036
Multi-residue determination of seven quinolones antibiotics in gilthead seabream using liquid chromatography-tandem mass spectrometry.	2008 Sep 5	18675423
Metabolism and excretion kinetics of 14C-labeled and non-labeled difloxacin in pigs after oral administration, and antimicrobial activity of manure containing difloxacin and its metabolites.	2009 Apr	19181312
Pharmacokinetics of fluoroquinolones in critical care patients: A bio-analytical HPLC method for the simultaneous quantification of ofloxacin, ciprofloxacin and moxifloxacin in human plasma.	2009 Apr 1	19272845
Quantitation and identity confirmation of residues of quinolones in tilapia fillets by LC-ESI-MS-MS QToF.	2009 Aug	19554313
High prevalence of multidrug-tolerant bacteria and associated antimicrobial resistance genes isolated from ornamental fish and their carriage water.	2009 Dec 21	20027306
Determination of fluoroquinolones in aquaculture products by ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS).	2009 Jan	19680869
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].	2009 Jan	19449537
Water-compatible molecularly imprinted polymer for the selective recognition of fluoroquinolone antibiotics in biological samples.	2009 Jan	18839153
Developing and optimizing an immunoaffinity cleanup technique for determination of quinolones from chicken muscle.	2009 Jan 28	19119842
[Simultaneous analysis of 7 fluoroquinolone residues in chicken muscle by ultra performance liquid chromatography-electrospray ionization tandem mass spectrometry].	2009 Jul	19938493
Phage therapy and photodynamic therapy: low environmental impact approaches to inactivate microorganisms in fish farming plants.	2009 Jul 30	19841715
Rapid method for the determination and confirmation of fluoroquinolone residues in catfish using liquid chromatography/fluorescence detection and liquid chromatography-tandem mass spectrometry.	2009 Jul-Aug	19714995
Primary photoprocesses in a fluoroquinolone antibiotic sarafloxacin.	2009 Jul-Aug	19508645
Solid-phase microextraction with micellar desorption and HPLC-fluorescence detection for the analysis of fluoroquinolones residues in water samples.	2009 Jun	19205671
Application of ionic liquids in high performance reversed-phase chromatography.	2009 Jun 4	19582220
Rapid determination of 19 quinolone residues in spiked fish and pig muscle by high-performance liquid chromatography (HPLC) tandem mass spectrometry.	2009 Mar	19680903
[Multi-residue determination of 11 quinolones in chicken muscle by high performance liquid chromatography with fluorescence detection].	2009 Mar	19626850
Ultra performance liquid chromatography tandem mass spectrometry performance evaluation for analysis of antibiotics in natural waters.	2009 Mar	19148627
Multiclass analysis of antibiotic residues in honey by ultraperformance liquid chromatography-tandem mass spectrometry.	2009 Mar 11	19195999
Simultaneous determination of eleven quinolones in animal feed by liquid chromatography with fluorescence and ultraviolet absorbance detection.	2009 Nov 13	19616214
Photolysis of difloxacin and sarafloxacin in aqueous systems.	2009 Oct	19751946
Microbial screening methods for detection of antibiotic residues in slaughter animals.	2009 Oct	19484227
In vitro residual anti-bacterial activity of difloxacin, sarafloxacin and their photoproducts after photolysis in water.	2009 Oct	19473738
Fluoroquinolone antibiotic determination in bovine, ovine and caprine milk using solid-phase extraction and high-performance liquid chromatography-fluorescence detection with ionic liquids as mobile phase additives.	2009 Oct 23	19268960
Quantification of danofloxacin and difloxacin in chicken tissues in the presence of sarafloxacin as interference.	2009 Sep 9	19689131
Single-step extraction followed by LC for determination of (fluoro)quinolone drug residues in muscle, eggs, and milk.	2010 Apr	20175091
Aquatic photochemistry of fluoroquinolone antibiotics: kinetics, pathways, and multivariate effects of main water constituents.	2010 Apr 1	20205456
Laser induced fluorescence coupled to capillary electrophoresis for the determination of fluoroquinolones in foods of animal origin using molecularly imprinted polymers.	2010 Apr 9	20227081
Sensitive determination of fluoroquinolone residues in waters by capillary electrophoresis with laser-induced fluorescence detection.	2010 Feb	20091154
Simultaneous determination of quinolones for veterinary use by high-performance liquid chromatography with electrochemical detection.	2010 Feb 1	20042380
Determination of fluoroquinolone residues in poultry muscle in Portugal.	2010 Jul	20496028
Fluoroquinolone antibiotics determination in piggeries environmental waters.	2010 Mar	20445852
Behaviour of (14)C-sulfadiazine and (14)C-difloxacin during manure storage.	2010 Mar 1	20022355
Effects of fish CYP inducers on difloxacin N-demethylation in kidney cell of Chinese idle (Ctenopharyngodon idellus).	2010 Sep	19685219

Patents

Sample Use Guides

In Vivo Use Guide

Rats: 40 mg/kg, injected intramuscularly three times a day at 4-h intervals.

Route of Administration: Intramuscular

In Vitro Use Guide

The MIC of sarafloxacin against five isolates and two reference strains of Mycoplasma gallisepticum (MG) (approximately 10(5) colony-forming units [CFU]/ml) was 0.37 ug/ml

Name

Type

Language

SARAFLOXACIN

Official Name

English

6-fluoro-1-(4-fluorophenyl)-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid

Systematic Name

English

DIFLOXACIN HYDROCHLORIDE TRIHYDRATE FOR VETERINARY USE IMPURITY B [EP IMPURITY]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 6-FLUORO-1-(4-FLUOROPHENYL)-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-

Systematic Name

English

ABBOTT-57135

Code

English

6-FLUORO-1-(P-FLUOROPHENYL)-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINECARBOXYLIC ACID

Systematic Name

English

sarafloxacin [INN]

Common Name

English

SARAFLOXACIN [HSDB]

Common Name

English

SARAFLOXACIN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795