Danofloxacin mesylate
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MedKoo CAT#: 524933

CAS#: 119478-55-6 (mesylate)

Description: Danofloxacin mesylate is a fluoroquinolone antibiotic used in veterinary medicine.

Chemical Structure

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Danofloxacin mesylate
CAS# 119478-55-6 (mesylate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 524933
Name: Danofloxacin mesylate
CAS#: 119478-55-6 (mesylate)
Chemical Formula: C20H24FN3O6S
Exact Mass: 0.00
Molecular Weight: 453.480
Elemental Analysis: C, 52.97; H, 5.33; F, 4.19; N, 9.27; O, 21.17; S, 7.07

Price and Availability

Size Price Availability Quantity
1g USD 250
5g USD 650
10g USD 950 2 Weeks
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Related CAS #: 112398-08-0 (free base)   119478-55-6 (mesylate)    

Synonym: Danofloxacin mesylate; CP 76,136-27; CP-76,136-27; Danofloxacin monomethanesulfonate.

IUPAC/Chemical Name: 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-((1S,4S)-5-methyl-2,5-diazabicyclo(2.2.1)hept-2-yl)-4-oxo-3-quinolinecarboxylic acid, monomethanesulfonate

InChi Key: APFDJSVKQNSTKF-FXMYHANSSA-N

InChi Code: InChI=1S/C19H20FN3O3.CH4O3S/c1-21-7-12-4-11(21)8-22(12)17-6-16-13(5-15(17)20)18(24)14(19(25)26)9-23(16)10-2-3-10;1-5(2,3)4/h5-6,9-12H,2-4,7-8H2,1H3,(H,25,26);1H3,(H,2,3,4)/t11-,12-;/m0./s1

SMILES Code: O=C(C1=CN(C2CC2)C3=C(C=C(F)C(N4[C@](C5)([H])CN(C)[C@]5([H])C4)=C3)C1=O)O.CS(=O)(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:
Product Data
Instruction:
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Biological target: Danofloxacin mesylate (CP 76136-27) is a synthetic antibacterial agent of the fluoroquinolone class that acts principally by the inhibition of bacterial DNA-gyrase.
In vitro activity: This study was performed to assess the neurotoxic effects of methylmercury, arsanilic acid and danofloxacin by quantification of neural-specific proteins in vitro. Quantitation of the protein markers during 14 days of differentiation indicated that the mouse ESCs were completely differentiated into neural cells by Day 8. Overall, DF exerted less toxic effects during both stages compared to the other chemicals (Fig. 5). At relatively high concentrations, DF increased POU5F1 expression during the differentiated stage more than the differentiating stage (10 µM vs. 40 µM; Fig. 5A). GABAA-R seemed to be affected by high doses during the differentiating stage while the expression levels during the differentiated stage were significantly decreased (p < 0.05) by DF at concentrations greater than 10 µM (Fig. 5B). GFAP and Tuj1 expression during the differentiated stage was significantly decreased by all concentrations of DF, but this effect was observed only at concentrations greater than 5 and 10 µM during the differentiating stage (Figs. 5C and E). The production of Nestin was significantly decreased (p < 0.05) by concentrations of DF greater than 10 µM during both stages (Fig. 5D). MAP2 expression during the differentiated stage was more sensitive to DF than during the differentiating stage (5 µM vs. 20 µM, p < 0.05; Fig. 5F). Reference: J Vet Sci. 2014 Mar; 15(1): 61–71. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3973767/
In vivo activity: In the present study, danofloxacin was orally administrated to the infected chickens once daily for 3 days by an established in vivo M. gallisepticum infection model. The PK profiles indicated that danofloxacin concentration in the lung tissues was higher than plasma. Mycoplasmacidal activity was achieved when infected chickens were exposed to danofloxacin at the dose group above 2.5 mg/kg. The ratios of AUC24/MIC (the area under the concentration-time curve over 24 h divided by the MIC) for 2 log10 (CFU) and 3 log10 (CFU) reduction were 31.97 and 97.98 L h/kg, respectively. Substitutions of Ser-83→Arg or Glu-87→Gly in gyrA; Glu-84→Lys in parC were observed in the resistant mutant strains that were selected from the dose group of 1 and 2.5 mg/kg. MICs of danofloxacin, enrofloxacin, ofloxacin, levofloxacin, gatifloxacin, and norfloxacin against the resistant mutant strains with a single mutation in position-83 were higher than that with a single mutation in position-87. These findings suggested that danofloxacin may be therapeutically effective to treat M. gallisepticum infection in chickens if administered at a dosage of 5.5 mg/kg once daily for 3 days. Reference: Front Microbiol. 2017 May 30;8:926. https://pubmed.ncbi.nlm.nih.gov/28611739/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 44.10
H2O 91.0 200.67

Preparing Stock Solutions

The following data is based on the product molecular weight 453.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Kang SJ, Jeong SH, Kim EJ, Park YI, Park SW, Shin HS, Son SW, Kang HG. Toxic effects of methylmercury, arsanilic acid and danofloxacin on the differentiation of mouse embryonic stem cells into neural cells. J Vet Sci. 2014;15(1):61-71. doi: 10.4142/jvs.2014.15.1.61. Epub 2013 Oct 18. PMID: 24136205; PMCID: PMC3973767. 2. Zhang N, Wu Y, Huang Z, Yao L, Zhang L, Cai Q, Shen X, Jiang H, Ding H. The PK-PD Relationship and Resistance Development of Danofloxacin against Mycoplasma gallisepticum in An In Vivo Infection Model. Front Microbiol. 2017 May 30;8:926. doi: 10.3389/fmicb.2017.00926. PMID: 28611739; PMCID: PMC5447713 3. Aliabadi FS, Landoni MF, Lees P. Pharmacokinetics (PK), pharmacodynamics (PD), and PK-PD integration of danofloxacin in sheep biological fluids. Antimicrob Agents Chemother. 2003 Feb;47(2):626-35. doi: 10.1128/AAC.47.2.626-635.2003. PMID: 12543670; PMCID: PMC151775.
In vitro protocol: 1. Kang SJ, Jeong SH, Kim EJ, Park YI, Park SW, Shin HS, Son SW, Kang HG. Toxic effects of methylmercury, arsanilic acid and danofloxacin on the differentiation of mouse embryonic stem cells into neural cells. J Vet Sci. 2014;15(1):61-71. doi: 10.4142/jvs.2014.15.1.61. Epub 2013 Oct 18. PMID: 24136205; PMCID: PMC3973767.
In vivo protocol: 1. Zhang N, Wu Y, Huang Z, Yao L, Zhang L, Cai Q, Shen X, Jiang H, Ding H. The PK-PD Relationship and Resistance Development of Danofloxacin against Mycoplasma gallisepticum in An In Vivo Infection Model. Front Microbiol. 2017 May 30;8:926. doi: 10.3389/fmicb.2017.00926. PMID: 28611739; PMCID: PMC5447713. 2. 2. Aliabadi FS, Landoni MF, Lees P. Pharmacokinetics (PK), pharmacodynamics (PD), and PK-PD integration of danofloxacin in sheep biological fluids. Antimicrob Agents Chemother. 2003 Feb;47(2):626-35. doi: 10.1128/AAC.47.2.626-635.2003. PMID: 12543670; PMCID: PMC151775.

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1: Rusch M, Kauschat A, Spielmeyer A, Römpp A, Hausmann H, Zorn H, Hamscher G. Biotransformation of the Antibiotic Danofloxacin by Xylaria longipes Leads to an Efficient Reduction of Its Antibacterial Activity. J Agric Food Chem. 2015 Aug 12;63(31):6897-904. doi: 10.1021/acs.jafc.5b02343. Epub 2015 Aug 4. PubMed PMID: 26189577.

2: Fan YC, Sheu SY, Lai HT, Chang MH, Chen PH, Lei YC, Kuo TF, Wang CY. Residue Depletion Study of Danofloxacin in Cultured Tilapia (Oreochromis mossambicus). J AOAC Int. 2015 May-Jun;98(3):575-9. doi: 10.5740/jaoacint.13-327. Epub 2015 May 28. PubMed PMID: 26025372.

3: Ruiz-Palomero C, Soriano ML, Valcárcel M. β-Cyclodextrin decorated nanocellulose: a smart approach towards the selective fluorimetric determination of danofloxacin in milk samples. Analyst. 2015 May 21;140(10):3431-8. doi: 10.1039/c4an01967a. Epub 2015 Mar 17. PubMed PMID: 25781312.

4: Otero JA, Barrera B, de la Fuente A, Prieto JG, Marqués M, Álvarez AI, Merino G. Short communication: The gain-of-function Y581S polymorphism of the ABCG2 transporter increases secretion into milk of danofloxacin at the therapeutic dose for mastitis treatment. J Dairy Sci. 2015 Jan;98(1):312-7. doi: 10.3168/jds.2014-8288. Epub 2014 Nov 7. PubMed PMID: 25465626.

5: Yang F, Sun N, Liu YM, Zeng ZL. Estimating danofloxacin withdrawal time in broiler chickens based on physiologically based pharmacokinetics modeling. J Vet Pharmacol Ther. 2015 Apr;38(2):174-82. doi: 10.1111/jvp.12162. Epub 2014 Sep 18. PubMed PMID: 25236844.

6: Lopez BS, Giguère S, Berghaus LJ, Mullins MA, Davis JL. Pharmacokinetics of danofloxacin and N-desmethyldanofloxacin in adult horses and their concentration in synovial fluid. J Vet Pharmacol Ther. 2015 Apr;38(2):123-9. doi: 10.1111/jvp.12152. Epub 2014 Sep 16. PubMed PMID: 25224604.

7: Manzoori JL, Amjadi M, Soltani N, Jouyban A. Spectrofluorimetric determination of cefixime using terbium-danofloxacin probe. Iran J Basic Med Sci. 2014;17(4):256-62. PubMed PMID: 24904718; PubMed Central PMCID: PMC4046237.

8: Han SR, Yu J, Lee SW. In vitro selection of RNA aptamers that selectively bind danofloxacin. Biochem Biophys Res Commun. 2014 Jun 13;448(4):397-402. doi: 10.1016/j.bbrc.2014.04.103. Epub 2014 May 2. PubMed PMID: 24792181.

9: Dimitrova DJ, Haritova AM, Dinev TD, Moutafchieva RG, Lashev LD. Comparative pharmacokinetics of danofloxacin in common pheasants, guinea fowls and Japanese quails after intravenous and oral administration. Br Poult Sci. 2014 Feb;55(1):120-5. doi: 10.1080/00071668.2013.871502. PubMed PMID: 24392829.

10: Kang SJ, Jeong SH, Kim EJ, Park YI, Park SW, Shin HS, Son SW, Kang HG. Toxic effects of methylmercury, arsanilic acid and danofloxacin on the differentiation of mouse embryonic stem cells into neural cells. J Vet Sci. 2014;15(1):61-71. Epub 2013 Oct 18. PubMed PMID: 24136205; PubMed Central PMCID: PMC3973767.

11: Barrera B, González-Lobato L, Otero JA, Real R, Prieto JG, Álvarez AI, Merino G. Effects of triclabendazole on secretion of danofloxacin and moxidectin into the milk of sheep: role of triclabendazole metabolites as inhibitors of the ruminant ABCG2 transporter. Vet J. 2013 Nov;198(2):429-36. doi: 10.1016/j.tvjl.2013.07.033. Epub 2013 Aug 6. PubMed PMID: 23981352.

12: Yu CH, Liu ZY, Sun LS, Li YJ, Zhang DS, Pan RT, Sun ZL. Effect of Danofloxacin on Reactive Oxygen Species Production, Lipid Peroxidation and Antioxidant Enzyme Activities in Kidney Tubular Epithelial Cell Line, LLC-PK1. Basic Clin Pharmacol Toxicol. 2013 Dec;113(6):377-84. doi: 10.1111/bcpt.12110. Epub 2013 Aug 5. PubMed PMID: 23855763.

13: Cengiz M, Sahinturk P. Assessment of synergistic interactions of danofloxacin and orbifloxacin against quinolone-resistant Escherichia coli isolated from animals by the checkerboard and time-kill methods. J Antibiot (Tokyo). 2013 Oct;66(10):629-31. doi: 10.1038/ja.2013.62. Epub 2013 Jun 19. PubMed PMID: 23778116.

14: Haritova A, Dimitrova D, Dinev T, Moutafchieva R, Lashev L. Comparative pharmacokinetics of enrofloxacin, danofloxacin, and marbofloxacin after intravenous and oral administration in Japanese quail (Coturnix coturnix japonica). J Avian Med Surg. 2013 Mar;27(1):23-31. PubMed PMID: 23772453.

15: Murillo Pulgarín JA, Alañón Molina A, Boras N. Direct determination of danofloxacin and flumequine in milk by use of fluorescence spectrometry in combination with partial least-squares calibration. J Agric Food Chem. 2013 Mar 20;61(11):2655-60. doi: 10.1021/jf3046285. Epub 2013 Mar 5. PubMed PMID: 23432704.

16: Otero JA, Real R, de la Fuente Á, Prieto JG, Marqués M, Álvarez AI, Merino G. The bovine ATP-binding cassette transporter ABCG2 Tyr581Ser single-nucleotide polymorphism increases milk secretion of the fluoroquinolone danofloxacin. Drug Metab Dispos. 2013 Mar;41(3):546-9. doi: 10.1124/dmd.112.049056. Epub 2012 Dec 10. PubMed PMID: 23230133.

17: Perez M, Otero JA, Barrera B, Prieto JG, Merino G, Alvarez AI. Inhibition of ABCG2/BCRP transporter by soy isoflavones genistein and daidzein: effect on plasma and milk levels of danofloxacin in sheep. Vet J. 2013 May;196(2):203-8. doi: 10.1016/j.tvjl.2012.09.012. Epub 2012 Oct 18. PubMed PMID: 23083838.

18: Kaur K, Saini SS, Malik AK, Singh B. Micelle enhanced and terbium sensitized spectrofluorimetric determination of danofloxacin in milk using molecularly imprinted solid phase extraction. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Oct;96:790-5. doi: 10.1016/j.saa.2012.07.083. Epub 2012 Aug 3. PubMed PMID: 22925903.

19: Speltini A, Sturini M, Maraschi F, Profumo A, Albini A. Microwave-assisted extraction and determination of enrofloxacin and danofloxacin photo-transformation products in soil. Anal Bioanal Chem. 2012 Sep;404(5):1565-9. doi: 10.1007/s00216-012-6249-3. Epub 2012 Jul 20. PubMed PMID: 22814972.

20: Kaur K, Saini S, Singh B, Malik AK. Highly sensitive synchronous fluorescence measurement of danofloxacin in pharmaceutical and milk samples using aluminium (III) enhanced fluorescence. J Fluoresc. 2012 Sep;22(5):1407-13. doi: 10.1007/s10895-012-1079-4. Epub 2012 Jun 24. PubMed PMID: 22730138.