Florfenicol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Florfenicol
Accession Number
DB11413
Type
Small Molecule
Groups
Experimental, Vet approved
Description

Florfenicol is a fluorinated synthetic analog of thiamphenicol.

Structure
Thumb
Synonyms
  • (-)-Florfenicol
  • D-threo-2,2-Dichloro-N-(alpha-(fluoromethyl)-beta-hydroxy-p-(methylsulfonyl)phenethyl)acetamide
  • Florfenicol
External IDs
SCH 25298 / SCH-25298
International/Other Brands
Nuflor / Nuflor gold
Categories
UNII
9J97307Y1H
CAS number
73231-34-2
Weight
Average: 358.21
Monoisotopic: 357.0004627
Chemical Formula
C12H14Cl2FNO4S
InChI Key
AYIRNRDRBQJXIF-NXEZZACHSA-N
InChI
InChI=1S/C12H14Cl2FNO4S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)/t9-,10-/m1/s1
IUPAC Name
2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
SMILES
CS(=O)(=O)C1=CC=C(C=C1)[C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Florfenicol is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Florfenicol is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Florfenicol is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Florfenicol is combined with Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Florfenicol.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Florfenicol.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Florfenicol.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Florfenicol.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Florfenicol.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Florfenicol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Picco EJ, Diaz DC, Valtorta SE, Boggi JC: Chronotoxicology of florfenicol. Chronobiol Int. 2001 May;18(3):567-72. [PubMed:11475424]
  2. Park BK, Lim JH, Kim MS, Hwang YH, Yun HI: Pharmacokinetics of florfenicol and its metabolite, florfenicol amine, in dogs. Res Vet Sci. 2008 Feb;84(1):85-9. Epub 2007 Jun 13. [PubMed:17570454]
  3. Blickwede M, Valentin-Weigand P, Schwarz S: Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus. J Antimicrob Chemother. 2004 Jul;54(1):286-8. Epub 2004 Jun 2. [PubMed:15175268]
  4. Kehrenberg C, Meunier D, Targant H, Cloeckaert A, Schwarz S, Madec JY: Plasmid-mediated florfenicol resistance in Pasteurella trehalosi. J Antimicrob Chemother. 2006 Jul;58(1):13-7. Epub 2006 May 2. [PubMed:16670108]
  5. Hayes JM, Eichman J, Katz T, Gilewicz R: Stability of florfenicol in drinking water. J AOAC Int. 2003 Jan-Feb;86(1):22-9. [PubMed:12607736]
  6. Lane VM, Villarroel A, Wetzlich SE, Clifford A, Taylor I, Craigmill AL: Tissue residues of florfenicol in sheep. J Vet Pharmacol Ther. 2008 Apr;31(2):178-80. doi: 10.1111/j.1365-2885.2007.00918.x. [PubMed:18307512]
  7. Cook AL, St Claire M, Sams R: Use of florfenicol in non-human primates. J Med Primatol. 2004 Jun;33(3):127-33. [PubMed:15102069]
  8. Varma KJ, Adams PE, Powers TE, Powers JD, Lamendola JF: Pharmacokinetics of florfenicol in veal calves. J Vet Pharmacol Ther. 1986 Dec;9(4):412-25. [PubMed:3806782]
  9. Illambas J, Potter T, Sidhu P, Rycroft AN, Cheng Z, Lees P: Pharmacodynamics of florfenicol for calf pneumonia pathogens. Vet Rec. 2013 Mar 30;172(13):340. doi: 10.1136/vr.101155. Epub 2013 Mar 12. [PubMed:23482237]
  10. Kehrenberg C, Schwarz S: Plasmid-borne florfenicol resistance in Pasteurella multocida. J Antimicrob Chemother. 2005 May;55(5):773-5. Epub 2005 Apr 6. [PubMed:15814600]
  11. Yu ZG, Geng ZX, Liu TF, Jiang F: In vitro and in vivo evaluation of an in situ forming gel system for sustained delivery of Florfenicol. J Vet Pharmacol Ther. 2015 Jun;38(3):271-7. doi: 10.1111/jvp.12171. Epub 2014 Oct 7. [PubMed:25287575]
  12. Xu M, Qian M, Zhang H, Ma J, Wang J, Wu H: Simultaneous determination of florfenicol with its metabolite based on modified quick, easy, cheap, effective, rugged, and safe sample pretreatment and evaluation of their degradation behavior in agricultural soils. J Sep Sci. 2015 Jan;38(2):211-7. doi: 10.1002/jssc.201400919. Epub 2014 Dec 18. [PubMed:25395188]
  13. Gao YQ, Gao NY, Deng Y, Yin DQ, Zhang YS: Degradation of florfenicol in water by UV/Na2S 2O 8 process. Environ Sci Pollut Res Int. 2015 Jun;22(11):8693-701. doi: 10.1007/s11356-014-4054-6. Epub 2015 Jan 9. [PubMed:25567063]
  14. Woerde DJ, Martin PA, Govendir M: Susceptibility of rapidly growing mycobacteria isolated from Australian cats to ivermectin, moxidectin, ceftiofur and florfenicol. J Feline Med Surg. 2015 Dec;17(12):1065-8. doi: 10.1177/1098612X14565497. Epub 2015 Jan 8. [PubMed:25572306]
  15. Fedeniuk RW, McKenzie D, Mizuno M, Neiser C, O'Byrne C, Shurmer B: Development and validation of determinative and confirmatory LC-MS/MS methodologies for total florfenicol and tulathromycin residues in bovine, equine and porcine kidney, liver and muscle tissues. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Mar 1;983-984:1-9. doi: 10.1016/j.jchromb.2014.12.035. Epub 2015 Jan 12. [PubMed:25612770]
  16. Chen H, Son S, Zhang F, Yan J, Li Y, Ding H, Ding L: Rapid preparation of molecularly imprinted polymers by microwave-assisted emulsion polymerization for the extraction of florfenicol in milk. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Mar 1;983-984:32-8. doi: 10.1016/j.jchromb.2015.01.003. Epub 2015 Jan 13. [PubMed:25614968]
  17. Mitchell SM, Ullman JL, Teel AL, Watts RJ: Hydrolysis of amphenicol and macrolide antibiotics: Chloramphenicol, florfenicol, spiramycin, and tylosin. Chemosphere. 2015 Sep;134:504-11. doi: 10.1016/j.chemosphere.2014.08.050. Epub 2015 Jan 21. [PubMed:25618189]
  18. Maaland MG, Mo SS, Schwarz S, Guardabassi L: In vitro assessment of chloramphenicol and florfenicol as second-line antimicrobial agents in dogs. J Vet Pharmacol Ther. 2015 Oct;38(5):443-50. doi: 10.1111/jvp.12204. Epub 2015 Jan 27. [PubMed:25623169]
  19. Guo L, Song S, Liu L, Peng J, Kuang H, Xu C: Comparsion of an immunochromatographic strip with ELISA for simultaneous detection of thiamphenicol, florfenicol and chloramphenicol in food samples. Biomed Chromatogr. 2015 Sep;29(9):1432-9. doi: 10.1002/bmc.3442. Epub 2015 Feb 10. [PubMed:25675893]
  20. Klaudia C, Alina W: The influence of enrofloxacin, florfenicol, ceftiofur and E. coli LPS interaction on T and B cells subset in chicks. Vet Res Commun. 2015 Mar;39(1):53-60. doi: 10.1007/s11259-015-9632-7. Epub 2015 Feb 10. [PubMed:25686865]
  21. Gaunt PS, Chatakondi N, Gao D, Endris R: Efficacy of Florfenicol for Control of Mortality Associated with Edwardsiella ictaluri in Three Species of Catfish. J Aquat Anim Health. 2015 Mar;27(1):45-9. doi: 10.1080/08997659.2014.976672. [PubMed:25706107]
  22. Peng G, He Q, Al-Hamadani SM, Zhou G, Liu M, Zhu H, Chen J: Dispersive liquid-liquid microextraction method based on solidification of floating organic droplet for the determination of thiamphenicol and florfenicol in environmental water samples. Ecotoxicol Environ Saf. 2015 May;115:229-33. doi: 10.1016/j.ecoenv.2015.02.025. Epub 2015 Feb 24. [PubMed:25723132]
  23. Pentecost RL, Niehaus AJ, Werle N, Lakritz J: Absorption and disposition of florfenicol after intravenous, intramuscular and subcutaneous dosing in alpacas. Res Vet Sci. 2015 Apr;99:199-203. doi: 10.1016/j.rvsc.2015.02.006. Epub 2015 Feb 16. [PubMed:25744433]
  24. Geng ZX, Li HM, Tian J, Liu TF, Yu ZG: Study of pharmacokinetics of an in situ forming gel system for controlled delivery of florfenicol in pigs. J Vet Pharmacol Ther. 2015 Dec;38(6):596-600. doi: 10.1111/jvp.12218. Epub 2015 Mar 16. [PubMed:25771961]
  25. Rottboll LA, Skovgaard K, Barington K, Jensen HE, Friis C: Intrabronchial Microdialysis: Effects of Probe Localization on Tissue Trauma and Drug Penetration into the Pulmonary Epithelial Lining Fluid. Basic Clin Pharmacol Toxicol. 2015 Oct;117(4):242-50. doi: 10.1111/bcpt.12403. Epub 2015 Apr 17. [PubMed:25827198]
  26. Pilehvar S, Gielkens K, Trashin SA, Dardenne F, Blust R, Wael K: (Electro)Sensing of Phenicol Antibiotics - A Review. Crit Rev Food Sci Nutr. 2015 Apr 1:0. [PubMed:25830490]
  27. Nasim A, Aslam B, Javed I, Ali A, Muhammad F, Raza A, Sindhu ZU: Determination of florfenicol residues in broiler meat and liver samples using RP-HPLC with UV-visible detection. J Sci Food Agric. 2016 Mar;96(4):1284-8. doi: 10.1002/jsfa.7220. Epub 2015 May 12. [PubMed:25886128]
  28. Jones ML, Washburn KE, Fajt VR, Rice S, Coetzee JF: Synovial fluid pharmacokinetics of tulathromycin, gamithromycin and florfenicol after a single subcutaneous dose in cattle. BMC Vet Res. 2015 Feb 7;11:26. doi: 10.1186/s12917-015-0346-4. [PubMed:25886555]
  29. Zhang Q, Tang SS, Qian MY, Wei L, Zhou D, Zhang ZJ, He JK, Zhang QJ, Zhu P, Xiao XL: Nanoemulsion formulation of florfenicol improves bioavailability in pigs. J Vet Pharmacol Ther. 2016 Feb;39(1):84-9. doi: 10.1111/jvp.12230. Epub 2015 Apr 20. [PubMed:25891823]
  30. Fedeniuk RW, Mizuno M, Neiser C, O'Byrne C: Development of LC-MS/MS methodology for the detection/determination and confirmation of chloramphenicol, chloramphenicol 3-O-beta-d-glucuronide, florfenicol, florfenicol amine and thiamphenicol residues in bovine, equine and porcine liver. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jun 1;991:68-78. doi: 10.1016/j.jchromb.2015.04.009. Epub 2015 Apr 10. [PubMed:25913426]
  31. Zhang A, Yang Y, Wang H, Lei C, Xu C, Guan Z, Liu B, Huang X, Peng L: PREVALENCE OF SULFONAMIDE AND FLORFENICOL RESISTANCE GENES IN ESCHERICHIA COLI ISOLATED FROM YAKS (BOS GRUNNIENS) AND HERDSMEN IN THE TIBETAN PASTURE. J Wildl Dis. 2015 Jul;51(3):626-33. doi: 10.7589/2014-09-234. Epub 2015 May 14. [PubMed:25973625]
  32. Sin DW, Ho C, Wong YT: Phenylboronic Acid Solid Phase Extraction Cleanup and Isotope Dilution Liquid Chromatography-Tandem Mass Spectrometry for the Determination of Florfenicol Amine in Fish Muscles. J AOAC Int. 2015 May-Jun;98(3):566-74. doi: 10.5740/jaoacint.14-267. Epub 2015 May 28. [PubMed:26025252]
  33. Bosse JT, Li Y, Atherton TG, Walker S, Williamson SM, Rogers J, Chaudhuri RR, Weinert LA, Holden MT, Maskell DJ, Tucker AW, Wren BW, Rycroft AN, Langford PR: Characterisation of a mobilisable plasmid conferring florfenicol and chloramphenicol resistance in Actinobacillus pleuropneumoniae. Vet Microbiol. 2015 Aug 5;178(3-4):279-82. doi: 10.1016/j.vetmic.2015.05.020. Epub 2015 May 28. [PubMed:26049592]
External Links
KEGG Drug
D04194
ChemSpider
102776
ChEBI
87185
ChEMBL
CHEMBL1241590
Wikipedia
Florfenicol

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.219 mg/mLALOGPS
logP0.98ALOGPS
logP0.67ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity78.19 m3·mol-1ChemAxon
Polarizability31.49 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-053u-2940000000-92c2497527c29726f568

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonyl compounds
Direct Parent
Benzenesulfonyl compounds
Alternative Parents
Sulfones / Secondary alcohols / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Organopnictogen compounds / Organonitrogen compounds / Organofluorides / Organochlorides / Organic oxides / Hydrocarbon derivatives
show 3 more
Substituents
Benzenesulfonyl group / Sulfone / Sulfonyl / Secondary alcohol / Carboximidic acid / Carboximidic acid derivative / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound / Organic oxide / Aromatic alcohol
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organofluorine compound, sulfone, secondary alcohol, organochlorine compound, carboxamide (CHEBI:87185)

Drug created on February 25, 2016 11:30 / Updated on June 04, 2019 07:20