Marbofloxacin

Marbofloxacin

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Marbofloxacin
Category Antibiotics
Catalog number BBF-04550
CAS 115550-35-1
Molecular Weight 362.36
Molecular Formula C17H19FN4O4
Purity >98%

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Description

Marbofloxacin is a third generation fluoroquinolone antibiotic. Marbofloxacin exhibits high bactericidal activity against a broad spectrum of aerobic Gram-negative and some Gram-positive bacteria, as well as Mycoplasma spp.

Specification

Related CAS 115551-26-3 (hydrochloride)
Synonyms 9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[3,2,1-ij][4,1,2]benzoxadiazine-6-carboxylic Acid; Marbocyl; Zeniquin; Marbofloxacinum
Storage Store at 2-8°C
IUPAC 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
Canonical SMILES CN1CCN(CC1)C2=C(C=C3C4=C2OCN(N4C=C(C3=O)C(=O)O)C)F
InChI 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)
InChI Key BPFYOAJNDMUVBL-UHFFFAOYSA-N
Source Synthetic

Properties

Appearance Pale Yellow Solid
Application Anti-Bacterial Agents
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Mycoplasma
Boiling Point 571°C
Melting Point >250°C (dec.)
Density 1.55±0.1 g/cm3 (Predicted)
Solubility Soluble in DMSO, Water, Ethanol

Reference Reading

1.In vitro Dynamic Pharmacokinetic/Pharmacodynamic (PK/PD) study and COPD of Marbofloxacin against Haemophilus parasuis.
Sun J1, Xiao X2,3, Huang RJ4, Yang T5, Chen Y6, Fang X7, Huang T8, Zhou YF9, Liu YH10,11. BMC Vet Res. 2015 Dec 1;11:293. doi: 10.1186/s12917-015-0604-5.
BACKGROUND: Haemophilus parasuis (H. parasuis) can invade the body and cause systemic infection under stress conditions. Marbofloxacin has been recommended for the treatment of swine infections. However, few studies have investigated the PK/PD characteristics and PK/PD cutoff (COPD) of this drug against H. parasuis.
2.Marbofloxacin-encapsulated microparticles provide sustained drug release for treatment of veterinary diseases.
Lee J1, Kwon HJ2, Ji H2, Cho SH1, Cho EH3, Han HD4, Shin BC5. Mater Sci Eng C Mater Biol Appl. 2016 Mar 1;60:511-7. doi: 10.1016/j.msec.2015.12.004. Epub 2015 Dec 4.
Fluoroquinolone antibiotics with concentration-dependent killing effects and a well-established broad spectrum of activity are used commonly to treat infectious diseases caused by bacteria. However, frequent and excessive administration of these antibiotics is a serious problem, and leads to increased number of drug-resistant bacteria. Thus, there is an urgent need for novel fluoroquinolone antibiotic formulations that minimize the risk of resistance while maximizing their efficacy. In this study, we developed intramuscularly injectable polymeric microparticles (MPs) that encapsulated with marbofloxacin (MAR) and were composed of poly(D,L-lactide-co-glycolic acid) (PLGA) and poloxamer (POL). MAR-encapsulated MP (MAR-MP) had a spherical shape with particle size ranging from 80 μm to 120 μm. Drug loading efficiency varied from 55 to 85% (w/w) at increasing amount of hydrophilic agent, POL. Drug release from MAR-MP demonstrated a significant and sustained increase at increased ratios of POL to PLGA.
3.Pharmacokinetics/pharmacodynamics of marbofloxacin in a Pasteurella multocida serious murine lung infection model.
Qu Y1, Qiu Z2, Cao C3, Lu Y4, Sun M5, Liang C6, Zeng Z7. BMC Vet Res. 2015 Dec 2;11:294. doi: 10.1186/s12917-015-0608-1.
BACKGROUND: Marbofloxacin is a third-generation fluoroquinolone developed solely for veterinary medicine with a broad spectrum of antibacterial activity against some Gram-positive and most Gram-negative bacteria, including the bovine respiratory tract pathogen, Pasteurella multocida. The objective of our study was to elucidate the pharmacokinetics and pharmacodynamics of marbofloxacin in a Pasteurella multocida infected murine lung model, and to estimate the magnitudes of pharmacokinetics-pharmacodynamics parameters associated with various effects.
4.Determination of marbofloxacin in plasma and synovial fluid by ultrafiltration followed by HPLC-MS/MS.
Montesano C1, Curini R1, Sergi M2, Compagnone D3, Celani G4, Varasano V4, Petrizzi L4, Amorena M3. J Pharm Biomed Anal. 2016 May 10;123:31-6. doi: 10.1016/j.jpba.2016.01.061. Epub 2016 Feb 1.
A rapid LC-MS/MS method for the determination of marbofloxacin in plasma and synovial fluid is presented in this study. The method uses a rapid sample preparation which only requires an ultrafiltration step with centrifugal filter devices. The optimized procedure allows a minimal need of sample (175μL), particularly useful for synovial fluid samples which amount is rather limited; it is simple, rapid and easily applicable providing anyhow a satisfactory clean up, demonstrated by post-infusion experiments. On the other hand to maximize the speed of the analysis an ultrafast chromatographic separation has been obtained by selecting a column of 20mm; the reduced run-time is suitable for processing numerous samples on a daily basis. Linearity was assessed in the range 5-2500ngmL(-1); ofloxacin was used as internal standard. LOD and LOQ were respectively 1 and 5ng/mL. The method was successfully applied to a set of samples generated during an experimental veterinary study.

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