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=C(C=C(F)C(=C3)N4CCNCC4)C1=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

Molecular Formula	C20H17F2N3O3
Molecular Weight	385.3641
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 8504
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 8504
Enterobacteriaceae 2 Target ID: CHEMBL614436 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3208547	Inhibitor 8504
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3539011	Inhibitor 8504

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
Effects of fish CYP inducers on difloxacin N-demethylation in kidney cell of Chinese idle (Ctenopharyngodon idellus).	2010-09	19685219
Determination of fluoroquinolone residues in poultry muscle in Portugal.	2010-07	20496028
Laser induced fluorescence coupled to capillary electrophoresis for the determination of fluoroquinolones in foods of animal origin using molecularly imprinted polymers.	2010-04-09	20227081
Aquatic photochemistry of fluoroquinolone antibiotics: kinetics, pathways, and multivariate effects of main water constituents.	2010-04-01	20205456
Single-step extraction followed by LC for determination of (fluoro)quinolone drug residues in muscle, eggs, and milk.	2010-04	20175091
Behaviour of (14)C-sulfadiazine and (14)C-difloxacin during manure storage.	2010-03-01	20022355
Fluoroquinolone antibiotics determination in piggeries environmental waters.	2010-03	20445852
Simultaneous determination of quinolones for veterinary use by high-performance liquid chromatography with electrochemical detection.	2010-02-01	20042380
Sensitive determination of fluoroquinolone residues in waters by capillary electrophoresis with laser-induced fluorescence detection.	2010-02	20091154
High prevalence of multidrug-tolerant bacteria and associated antimicrobial resistance genes isolated from ornamental fish and their carriage water.	2009-12-21	20027306
Simultaneous determination of eleven quinolones in animal feed by liquid chromatography with fluorescence and ultraviolet absorbance detection.	2009-11-13	19616214
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.	2009-10-23	19268960
Photolysis of difloxacin and sarafloxacin in aqueous systems.	2009-10	19751946
Microbial screening methods for detection of antibiotic residues in slaughter animals.	2009-10	19484227
In vitro residual anti-bacterial activity of difloxacin, sarafloxacin and their photoproducts after photolysis in water.	2009-10	19473738
Quantification of danofloxacin and difloxacin in chicken tissues in the presence of sarafloxacin as interference.	2009-09-09	19689131
Rapid method for the determination and confirmation of fluoroquinolone residues in catfish using liquid chromatography/fluorescence detection and liquid chromatography-tandem mass spectrometry.	2009-09-01	19714995
Quantitation and identity confirmation of residues of quinolones in tilapia fillets by LC-ESI-MS-MS QToF.	2009-08	19554313
Phage therapy and photodynamic therapy: low environmental impact approaches to inactivate microorganisms in fish farming plants.	2009-07-30	19841715
[Simultaneous analysis of 7 fluoroquinolone residues in chicken muscle by ultra performance liquid chromatography-electrospray ionization tandem mass spectrometry].	2009-07	19938493
Primary photoprocesses in a fluoroquinolone antibiotic sarafloxacin.	2009-06-11	19508645
Application of ionic liquids in high performance reversed-phase chromatography.	2009-06-04	19582220
Solid-phase microextraction with micellar desorption and HPLC-fluorescence detection for the analysis of fluoroquinolones residues in water samples.	2009-06	19205671
Pharmacokinetics of fluoroquinolones in critical care patients: A bio-analytical HPLC method for the simultaneous quantification of ofloxacin, ciprofloxacin and moxifloxacin in human plasma.	2009-04-01	19272845
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.	2009-04	19181312
Multiclass analysis of antibiotic residues in honey by ultraperformance liquid chromatography-tandem mass spectrometry.	2009-03-11	19195999
Rapid determination of 19 quinolone residues in spiked fish and pig muscle by high-performance liquid chromatography (HPLC) tandem mass spectrometry.	2009-03	19680903
[Multi-residue determination of 11 quinolones in chicken muscle by high performance liquid chromatography with fluorescence detection].	2009-03	19626850
Ultra performance liquid chromatography tandem mass spectrometry performance evaluation for analysis of antibiotics in natural waters.	2009-03	19148627
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.	2009-02-11	19202815
Developing and optimizing an immunoaffinity cleanup technique for determination of quinolones from chicken muscle.	2009-01-28	19119842
Determination of fluoroquinolones in aquaculture products by ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS).	2009-01	19680869
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].	2009-01	19449537
Water-compatible molecularly imprinted polymer for the selective recognition of fluoroquinolone antibiotics in biological samples.	2009-01	18839153
Trace analysis of quinolone and fluoroquinolone antibiotics from wastewaters by liquid chromatography-electrospray tandem mass spectrometry.	2008-12-19	19007934
Ionic liquids as mobile phase additives for the high-performance liquid chromatographic analysis of fluoroquinolone antibiotics in water samples.	2008-12	18854988
Simultaneous determination of quinolone antibacterials in bovine milk by liquid chromatography-mass spectrometry.	2008-11	18651586
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.	2008-10-31	18829036
Solid-phase extraction of fluoroquinolones from aqueous samples using a water-compatible stochiometrically imprinted polymer.	2008-10-24	18790491
Multi-residue determination of seven quinolones antibiotics in gilthead seabream using liquid chromatography-tandem mass spectrometry.	2008-09-05	18675423
[Multiresidue determination of quinolones in animal and fishery products by HPLC].	2008-06	18633210
In-line solid-phase extraction preconcentration in capillary electrophoresis-tandem mass spectrometry for the multiresidue detection of quinolones in meat by pressurized liquid extraction.	2008-05	18409156
Endotoxemic pulmonary hypertension is largely mediated by endothelin-induced venous constriction.	2008-05	18214440
Multiclass determination and confirmation of antibiotic residues in honey using LC-MS/MS.	2008-03-12	18257525
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.	2008-01	18081209
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.	2007-11-15	17977806
Multiresidue method for simultaneous determination of quinolone antibacterials in pig kidney samples by liquid chromatography with fluorescence detection.	2007-11-15	17951118
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.	2007-11	17763524
Multiresidue HPLC analysis of ten quinolones in milk after solid phase extraction: validation according to the European Union Decision 2002/657/EC.	2007-10	17683042
[Determination of 16 quinolone residues in animal tissues using high performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry].	2007-07	17970104

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

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:20:18 GMT 2025` Edited by `admin` on `Wed Apr 02 09:20:18 GMT 2025`
Record UNII	RC3WJ907XY
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ABBOTT-57135

Preferred Name

English

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

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