Danofloxacin free base
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MedKoo CAT#: 526066

CAS#: 112398-08-0 (free base)

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

Chemical Structure

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Danofloxacin free base
CAS# 112398-08-0 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 526066
Name: Danofloxacin free base
CAS#: 112398-08-0 (free base)
Chemical Formula: C19H20FN3O3
Exact Mass: 357.15
Molecular Weight: 357.385
Elemental Analysis: C, 63.86; H, 5.64; F, 5.32; N, 11.76; O, 13.43

Price and Availability

Size Price Availability Quantity
100mg USD 350 2 Weeks
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Related CAS #: 112398-08-0 (free base)   119478-55-6 (mesylate)    

Synonym: Danofloxacine; Danofloxacin; Danofloxacino;

IUPAC/Chemical Name: 1-Cyclopropyl-6-fluoro-7-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-4-oxoquinoline-3-carboxylic acid

InChi Key: QMLVECGLEOSESV-RYUDHWBXSA-N

InChi Code: InChI=1S/C19H20FN3O3/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/h5-6,9-12H,2-4,7-8H2,1H3,(H,25,26)/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

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

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 is a third generation fluoroquinolone antimicrobial agent that shows a broad spectrum of activity against most Gramnegative and Gram-positive bacteria, mycoplasma and chlamydia species, and plays an antimicrobial role by 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 25.0 70.00

Preparing Stock Solutions

The following data is based on the product molecular weight 357.39 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. 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. 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. 3. . 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 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. 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: Klein U, de Jong A, Moyaert H, El Garch F, Leon R, Richard-Mazet A, Rose M, Maes D, Pridmore A, Thomson JR, Ayling RD. Antimicrobial susceptibility monitoring of Mycoplasma hyopneumoniae and Mycoplasma bovis isolated in Europe. Vet Microbiol. 2017 May;204:188-193. doi: 10.1016/j.vetmic.2017.04.012. Epub 2017 Apr 14. PubMed PMID: 28532800.

2: Serrano-Rodríguez JM, Cárceles-García C, Cárceles-Rodríguez CM, Gabarda ML, Serrano-Caballero JM, Fernández-Varón E. Susceptibility and PK/PD relationships of Staphylococcus aureus strains from ovine and caprine with clinical mastitis against five veterinary fluoroquinolones. Vet Rec. 2017 Apr 15;180(15):376. doi: 10.1136/vr.103964. Epub 2017 Feb 17. PubMed PMID: 28213532.

3: Teglia CM, Cámara MS, Vera-Candioti L. Dispersive liquid-liquid microextraction of quinolones in porcine blood: Validation of a CE method using univariate calibration or multivariate curve resolution-alternating least squares for overlapped peaks. Electrophoresis. 2017 Apr;38(8):1122-1129. doi: 10.1002/elps.201600475. Epub 2017 Mar 6. PubMed PMID: 28177131.

4: Yao M, Gao W, Tao H, Yang J, Huang T. The regulation effects of danofloxacin on pig immune stress induced by LPS. Res Vet Sci. 2017 Feb;110:65-71. doi: 10.1016/j.rvsc.2016.11.005. Epub 2016 Nov 6. PubMed PMID: 28159239.

5: Yassine M, Rifai A, Doumyati S, Trivella A, Mazellier P, Budzinski H, Al Iskandarani M. Oxidation of danofloxacin by free chlorine-kinetic study, structural identification of by-products by LC-MS/MS and potential toxicity of by-products using in silico test. Environ Sci Pollut Res Int. 2017 Mar;24(9):7982-7993. doi: 10.1007/s11356-017-8409-7. Epub 2017 Jan 20. PubMed PMID: 28108916.

6: Sweeney MT, Papich MG, Watts JL. New interpretive criteria for danofloxacin antibacterial susceptibility testing against Mannheimia haemolytica and Pasteurella multocida associated with bovine respiratory disease. J Vet Diagn Invest. 2017 Mar;29(2):224-227. doi: 10.1177/1040638716683212. Epub 2017 Jan 8. PubMed PMID: 28064562.

7: Zhang N, Ye X, Wu Y, Huang Z, Gu X, Cai Q, Shen X, Jiang H, Ding H. Determination of the Mutant Selection Window and Evaluation of the Killing of Mycoplasma gallisepticum by Danofloxacin, Doxycycline, Tilmicosin, Tylvalosin and Valnemulin. PLoS One. 2017 Jan 4;12(1):e0169134. doi: 10.1371/journal.pone.0169134. eCollection 2017. PubMed PMID: 28052123; PubMed Central PMCID: PMC5215565.

8: Santoke H, Cooper WJ. Environmental photochemical fate of selected pharmaceutical compounds in natural and reconstituted Suwannee River water: Role of reactive species in indirect photolysis. Sci Total Environ. 2017 Feb 15;580:626-631. doi: 10.1016/j.scitotenv.2016.12.008. Epub 2016 Dec 20. PubMed PMID: 28011020.

9: Terrado-Campos D, Tayeb-Cherif K, Peris-Vicente J, Carda-Broch S, Esteve-Romero J. Determination of oxolinic acid, danofloxacin, ciprofloxacin, and enrofloxacin in porcine and bovine meat by micellar liquid chromatography with fluorescence detection. Food Chem. 2017 Apr 15;221:1277-1284. doi: 10.1016/j.foodchem.2016.11.029. Epub 2016 Nov 8. PubMed PMID: 27979089.

10: Moreno LZ, da Costa BL, Matajira CE, Gomes VT, Mesquita RE, Silva AP, Moreno AM. Molecular and antimicrobial susceptibility profiling of Streptococcus dysgalactiae isolated from swine. Diagn Microbiol Infect Dis. 2016 Oct;86(2):178-80. doi: 10.1016/j.diagmicrobio.2016.07.020. Epub 2016 Jul 27. PubMed PMID: 27539863.

11: Mzyk DA, Baynes RE, Messenger KM, Martinez M, Smith GW. Pharmacokinetics and distribution in interstitial and pulmonary epithelial lining fluid of danofloxacin in ruminant and preruminant calves. J Vet Pharmacol Ther. 2017 Apr;40(2):179-191. doi: 10.1111/jvp.12346. Epub 2016 Jul 31. PubMed PMID: 27476495.

12: Ferrone V, Carlucci M, Palumbo P, Carlucci G. Development and validation of a MEPS-UHPLC-PDA method for determination of ulifloxacin in human plasma and urine of patients with peripheral arterial disease. J Pharm Biomed Anal. 2016 Sep 5;128:313-21. doi: 10.1016/j.jpba.2016.06.001. Epub 2016 Jun 4. PubMed PMID: 27318081.

13: Chen M, Wen F, Wang H, Zheng N, Wang J. Effect of various storage conditions on the stability of quinolones in raw milk. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2016 Jul;33(7):1147-54. doi: 10.1080/19440049.2016.1184051. Epub 2016 Jun 9. PubMed PMID: 27258809.

14: Otero JA, García-Mateos D, de la Fuente A, Prieto JG, Álvarez AI, Merino G. Effect of bovine ABCG2 Y581S polymorphism on concentrations in milk of enrofloxacin and its active metabolite ciprofloxacin. J Dairy Sci. 2016 Jul;99(7):5731-8. doi: 10.3168/jds.2015-10593. Epub 2016 May 4. PubMed PMID: 27157572.

15: Halwachs S, Kneuer C, Gohlsch K, Müller M, Ritz V, Honscha W. The ABCG2 efflux transporter from rabbit placenta: Cloning and functional characterization. Placenta. 2016 Feb;38:8-15. doi: 10.1016/j.placenta.2015.12.005. Epub 2015 Dec 12. PubMed PMID: 26907376.

16: Braun U, Hässig M, Previtali M, Franchini M, Vögtlin A, Storset AK, Ackermann M. [Interleukin-2 for the treatment of cows with malignant catarrhal fever]. Schweiz Arch Tierheilkd. 2015 Jan;157(1):31-8. German. PubMed PMID: 26753317.

17: 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.

18: Lin L, Zhang Y, Tu X, Xie L, Yue Z, Kang H, Wu W, Luo Y. [Determination of 25 quinolones in cosmetics by liquid chromatography-tandem mass spectrometry]. Se Pu. 2015 Mar;33(3):275-81. Chinese. PubMed PMID: 26182469.

19: Bearson BL, Brunelle BW. Fluoroquinolone induction of phage-mediated gene transfer in multidrug-resistant Salmonella. Int J Antimicrob Agents. 2015 Aug;46(2):201-4. doi: 10.1016/j.ijantimicag.2015.04.008. Epub 2015 May 28. PubMed PMID: 26078016.

20: Yánez-Jácome GS, Aguilar-Caballos MP, Gómez-Hens A. Luminescent determination of quinolones in milk samples by liquid chromatography/post-column derivatization with terbium oxide nanoparticles. J Chromatogr A. 2015 Jul 31;1405:126-32. doi: 10.1016/j.chroma.2015.05.070. Epub 2015 Jun 5. PubMed PMID: 26077970.