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Marbofloxacin

Alias: Zeniquin; Forcyl; Kelacyl; Zeniquin; Marbofloxacin; 115550-35-1; Marbocyl; Zeniquin; Marbofloxacine; Marbofloxacino; Marbofloxacinum; Marbofloxacine [INN-French]; Aristos; Boflox; Marbocyl; Aurizon
Cat No.:V1422 Purity: ≥98%
Marbofloxacin (Forcyl, Kelacyl,Zeniquin, Aristos, Boflox, Marbocyl, Aurizon), a carboxylic acid derivative, is a 3rd generation and broad spectrum antibiotic of the fluoroquinolone class used as a veterinary medication.
Marbofloxacin
Marbofloxacin Chemical Structure CAS No.: 115550-35-1
Product category: Topoisomerase
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
2g
5g
10g
Other Sizes

Other Forms of Marbofloxacin:

  • Marbofloxacin hydrochloride
Official Supplier of:
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Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Marbofloxacin (Forcyl, Kelacyl, Zeniquin, Aristos, Boflox, Marbocyl, Aurizon), a carboxylic acid derivative, is a 3rd generation and broad spectrum antibiotic of the fluoroquinolone class used as a veterinary medication. Marbofloxacin showed notable antibacterial activity against both gram–and + bacteria.

Biological Activity I Assay Protocols (From Reference)
Targets
Topoisomerase IV; Topoisomerase II
ln Vitro

Marbofloxacin is an antimicrobial fluoroquinolone that was created specifically for veterinary use. High bactericidal activity is demonstrated by marbofloxacin against Mycoplasma spp. and a wide range of aerobic Gram-negative and some Gram-positive bacteria. Marbofloxacin, a third-generation fluoroquinolone, primarily targets enzymes involved in transcription and replication, including DNA gyrase and topoisomerase IV, both of which are critical to the survival of bacteria. During the exponential phase, but not the lag phase, marbofloxacin exhibits a mycoplasmacidal effect on M. hyopneumoniae 116 wild-type strain and a clone that was isolated 4 days after in vivo treatment with the therapeutic dose.[1] In a dose-dependent manner, marbofloxacin significantly kills Leishmania promastigotes and intracellular amastigotes, outperforming sodium stibogluconate and meglumine antimoniate. Following Marbofloxacin therapy, the NO synthase pathway confers enhanced antileishmanial activity and infection resistance in macrophages.[2]

ln Vivo
Marbofloxacin treatment at the therapeutic dose is not effective in significantly reducing clinical signs and does not eradicate M. hyopneumoniae, as 87.5 to 100% of the pigs remain positive at the conclusion of the assays. However, treatment with marbofloxacin appears to lower the lung lesion scores.[1] Treating a Staphylococcus aureus infection in tissue cages in ponies with a once-daily dose of marbofloxacin at a dose of 6 mg/kg for seven days does not effectively eradicate S. aureus infections from isolated locations.[3]
Animal Protocol
SPF piglets inoculated intratracheally with M. hyopneumoniae strain 116
~2 mg/kg/day
Intramuscular injection
Tissue cages (TC), implanted subcutaneously in the neck in eight ponies, were inoculated with Staphylococcus aureus (S. aureus) to determine the clinical efficacy of marbofloxacin in the treatment of this infection. From 21 h after inoculation, marbofloxacin (6 mg/kg) was administered intravenously (i.v.) once daily for 7 days. Samples of the tissue cage fluid (TCF) were taken to determine marbofloxacin concentrations (days 1, 3 and 7), using high-pressure liquid chromatography, and numbers of viable bacteria [colony forming units (CFU)] (days 1, 3, 7, 14 and 21). Statistical analysis was used to compare CFU before and after treatment. Clinical signs and CFU were used to evaluate the efficacy of treatment. Although, there was a slight decrease in CFU in all TC initially, the infection was not eliminated by marbofloxacin treatment in any of the ponies and abscesses formed. As the MIC (0.25 microg/mL) did not change during treatment and the concentration of marbofloxacin during treatment (mean concentration in TCF was 0.89 microg/mL on day 1, 0.80 microg/mL on day 3 and 2.77 microg/mL on day 7) was above MIC, we consider that the treatment failure might be attributable to the formation of a biofilm by S. aureus. Based on the present results, i.v. administration of marbofloxacin alone is not suitable for the elimination of S. aureus infections from secluded sites.[2]
ADME/Pharmacokinetics
Marbofloxacin is a fluoroquinolone antibiotic expected to be effective in the treatment of infections involving gram-negative and some gram-positive bacteria in horses. In order to design a rational dosage regimen for the substance in horses, the pharmacokinetic properties of marbofloxacin were investigated in 6 horses after i.v., subcutaneous and oral administration of a single dose of 2 mg/kg bwt and the minimal inhibitory concentrations (MIC) assessed for bacteria isolated from equine infectious pathologies. The clearance of marbofloxacin was mean +/- s.d. 0.25 +/- 0.05 l/kg/h and the terminal half-life 756 +/- 1.99 h. The marbofloxacin absolute bioavailabilities after subcutaneous and oral administration were 98 +/- 11% and 62 +/- 8%, respectively. The MIC required to inhibit 90% of isolates (MIC90) was 0.027 microg/ml for enterobacteriaceae and 0.21 microg/ml for Staphylococcus aureus. The values of surrogate markers of antimicrobial efficacy (AUIC, Cmax/MIC ratio, time above MIC90) were calculated and the marbofloxacin concentration profiles simulated for repeated administrations. These data were used to determine rational dosage regimens for target bacteria. Considering the breakpoint values of efficacy indices for fluoroquinolones, a marbofloxacin dosage regimen of 2 mg/kg bwt/24 h by i.v., subcutaneous or oral routes was more appropriate for enterobacteriaceae than for S. aureus. [3]
Toxicity/Toxicokinetics
mouse LD50 oral >2 gm/kg United States Patent Document., #4801584
References

[1]. Marbofloxacin. Acta Crystallogr Sect E Struct Rep Online. 2012 Apr 1;68(Pt 4):o998-9.

[2]. Clinical efficacy of intravenous administration of marbofloxacin in a Staphylococcus aureus infection in tissue cages in ponies. J Vet Pharmacol Ther. 2006 Dec;29(6):555-60.

[3]. Pharmacokinetics of marbofloxacin in horses. Equine Vet J. 2002 Jul;34(4):366-72.

Additional Infomation
LSM-5799 is a member of quinolines.
Marbofloxacin is a carboxylic acid, part of the third generation of antibiotic fluoroquinolones. It is used in veterinary medicine. A formulation of marbofloxacin combined with clotrimazole and dexamethasone is available under the name Aurizon.
IN THE TITLE COMPOUND, [SYSTEMATIC NAME: 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-piperazin-1-yl)-7-oxo-7H-pyrido[1,2,3-ij][1,2,4]benzoxadiazine-6-carb-oxy-lic acid], C(17)H(19)FN(4)O(4), the carbonyl and carboxyl groups are coplanar with the quinoline ring, making a dihedral angle of 2.39 (2)°. The piperazine ring adopts a chair conformation and the oxadiazinane ring displays an envelope conformation with the CH(2) group at the flap displaced by 0.650 (2) Å from the plane through the other five atoms. The mol-ecular structure exhibits an S(6) ring motif, owing to an intra-molecular O-H⋯O hydrogen bond. In the crystal, weak C-H⋯F hydrogen bonds link mol-ecules into layers parallel to the ab plane.[1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H19FN4O4
Molecular Weight
362.36
Exact Mass
362.139
Elemental Analysis
C, 56.35; H, 5.29; F, 5.24; N, 15.46; O, 17.66
CAS #
115550-35-1
Related CAS #
115551-26-3
PubChem CID
60651
Appearance
Light yellow to yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
570.5±60.0 °C at 760 mmHg
Melting Point
268-269ºC
Flash Point
298.8±32.9 °C
Vapour Pressure
0.0±1.7 mmHg at 25°C
Index of Refraction
1.701
LogP
-0.55
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
2
Heavy Atom Count
26
Complexity
636
Defined Atom Stereocenter Count
0
SMILES
FC1C([H])=C2C(C(C(=O)O[H])=C([H])N3C2=C(C=1N1C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])C1([H])[H])OC([H])([H])N3C([H])([H])[H])=O
InChi Key
BPFYOAJNDMUVBL-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H19FN4O4/c1-19-3-5-21(6-4-19)14-12(18)7-10-13-16(14)26-9-20(2)22(13)8-11(15(10)23)17(24)25/h7-8H,3-6,9H2,1-2H3,(H,24,25)
Chemical Name
7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1,2-diazatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
Synonyms
Zeniquin; Forcyl; Kelacyl; Zeniquin; Marbofloxacin; 115550-35-1; Marbocyl; Zeniquin; Marbofloxacine; Marbofloxacino; Marbofloxacinum; Marbofloxacine [INN-French]; Aristos; Boflox; Marbocyl; Aurizon
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~3 mg/mL (~8.3 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
1%DMSO+30% polyethylene glycol+1%Tween 80, pH 4: 14mg/mL
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.7597 mL 13.7984 mL 27.5969 mL
5 mM 0.5519 mL 2.7597 mL 5.5194 mL
10 mM 0.2760 mL 1.3798 mL 2.7597 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Molecular structure of marbofloxacin showing atom-labelling scheme and displacement ellipsoids at 40% probability level. H atoms are shown as small circles of arbitary radii. Acta Crystallogr Sect E Struct Rep Online . 2012 Apr 1;68(Pt 4):o998-9.
  • Part of the crystal packing of Marbofloxacin. Acta Crystallogr Sect E Struct Rep Online . 2012 Apr 1;68(Pt 4):o998-9.
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