Marbofloxacin

  • CAT Number: A000875
  • CAS Number: 115550-35-1
  • Molecular Formula: C17H19FN4O4
  • Molecular Weight: 362.36
  • Purity: ≥95%
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Marbofloxacin(CAS: 115550-35-1) is a third generation fluoroquinolone antibiotic and is freely soluble in aqueous solution.<br />
Marbofloxacin is a carboxylic acid, part of the third generation of antibiotic fluoroquinolones. It is used in veterinary. A formulation of marbofloxacin combined with clotrimazole and dexamethasone is available under the name Aurizon.<br />
Fluoroquinolone antibiotics target bacterial DNA gyrase, an enzyme which reduces DNA strain during replication. Because DNA gyrase is required during DNA replication, subsequent DNA synthesis and ultimately cell division is inhibited.

Catalog Number A000875
CAS Number 115550-35-1
Molecular Formula

C17H19FN4O4

Purity 95%
Target Antibiotic
Solubility Limited solubility
Storage 3 years -20C powder
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
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)
InChIKey BPFYOAJNDMUVBL-UHFFFAOYSA-N
SMILES CN1CCN(CC1)C2=C(C=C3C4=C2OCN(N4C=C(C3=O)C(=O)O)C)F
Reference

[1]. Vet Microbiol. 2018 Apr;217:112-120. doi: 10.1016/j.vetmic.2018.03.006. Epub 2018 Mar 10.<br />
Consecutive antibiotic treatment with doxycycline and marbofloxacin clears bacteremia in Mycoplasma haemofelis-infected cats.<br />
Novacco M(1), Sugiarto S(2), Willi B(3), Baumann J(4), Spiri AM(2), Oestmann A(2), Riond B(2), Boretti FS(5), Naegeli H(6), Hofmann-Lehmann R(2).<br />
Author information: (1)Clinical Laboratory, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland; Center for Clinical Studies, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland. Electronic address: [email protected]. (2)Clinical Laboratory, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland; Center for Clinical Studies, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland. (3)Clinical Laboratory, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland; Clinic for Small Animal Internal Medicine, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland. (4)Clinical Laboratory, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland. (5)Center for Clinical Studies, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland; Clinic for Small Animal Internal Medicine, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland. (6)Center for Clinical Studies, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland; Institute of Pharmacology and Toxicology, Vetsuisse Faculty, University of Zurich, Zurich, Switzerland.<br />
Mycoplasma haemofelis is the most pathogenic feline hemoplasma species and a causative agent of infectious hemolytic anemia in cats. Current treatment protocols are effective in reducing M. haemofelis blood loads and clinical signs but consistent bacteremia clearance is rarely achieved. The aim of this study was to develop an antibiotic treatment protocol capable of clearing M. haemofelis bacteremia. Doxycycline and marbofloxacin treatment protocols were evaluated in chronically M. haemofelis infected cats in two pre-experiments and a controlled treatment study (main experiment) using five treated and four untreated cats. The blood bacterial loads in the main experiment were monitored weekly by real-time PCR for 203 days. Cats were treated with doxycycline (5 mg/kg bid orally) for 28 days. Cats that remained M. haemofelis PCR-positive or became positive again (all 5 cats in the main experiment) were switched to marbofloxacin treatment (2 mg/kg sid orally) for 14 days; then, all cats were PCR-negative. Immunosuppression after the antibiotic treatment did not lead to reactivation of bacteremia. Fine needle aspirates of different organs and bone marrow collected before and after immunosuppression were PCR-negative. Overall, 5 cats cleared bacteremia with doxycycline alone (showing lower bacterial loads at the treatment start), while 10 cats needed to be switched to marbofloxacin. Based on our results, we recommend doxycycline treatment (10 mg/kg up to 28 days) for clearance of M. haemofelis infection and monitoring bacterial loads by real-time PCR. Only if bacteremia persists or reoccurs, antibiotic treatment should be switched to marbofloxacin (2 mg/kg sid for 14 days).<br />
DOI: 10.1016/j.vetmic.2018.03.006 PMID: 29615243 [Indexed for MEDLINE]<br />
<br />
[2]. Trop Anim Health Prod. 2019 Nov;51(8):2603-2610. doi: 10.1007/s11250-019-01980-5. Epub 2019 Jun 23.<br />
The effects of Mannheimia haemolytica and albendazole on marbofloxacin pharmacokinetics in lambs.<br />
Altan F(1), Sayin Ipek DN(2), Corum O(3), Yesilmen Alp S(4), Ipek P(5), Uney K(6).<br />
Author information: (1)Department of Pharmacology and Toxicology, Faculty of Veterinary Medicine, University of Dicle, Diyarbakir, Turkey. [email protected]. (2)Department of Parasitology, Faculty of Veterinary Medicine, University of Dicle, Diyarbakir, Turkey. (3)Department of Pharmacology and Toxicology, Faculty of Veterinary Medicine, University of Kastamonu, Kastamonu, Turkey. (4)Department of Microbiology, Faculty of Veterinary Medicine, University of Dicle, Diyarbakir, Turkey. (5)Department of Physiology, Faculty of Veterinary Medicine, University of Dicle, Diyarbakir, Turkey. (6)Department of Pharmacology and Toxicology, Faculty of Veterinary Medicine, University of Selcuk, Konya, Turkey.<br />
The study aimed to define the effects of M. haemolytica and a single oral dose of albendazole on the single-dose pharmacokinetics of marbofloxacin in lambs. The pharmacokinetic-pharmacodynamic integration of marbofloxacin was applied to describe a 3&nbsp;mg/kg intramuscular dose in lambs. The 6 healthy and 12 naturally infected with M. haemolytica lambs (Akkaraman, males weighing 10-15&nbsp;kg and aged 2-3&nbsp;months) were used in this study. In the marbofloxacin group, 6 healthy lambs received marbofloxacin. In the albendazole group after 2&nbsp;weeks washout period, the same animals received marbofloxacin on 1&nbsp;h after albendazole. In the diseased marbofloxacin group, 6 lambs naturally infected with M. haemolytica received marbofloxacin. In the diseased albendazole group, 6 lambs naturally infected with M. haemolytica received marbofloxacin on 1&nbsp;h after albendazole. The marbofloxacin and albendazole were administered each as a single dose of 3&nbsp;mg/kg intramuscular and 7.5&nbsp;mg/kg oral, respectively, in the respective groups. Plasma concentration of marbofloxacin was measured with HPLC-UV and pharmacokinetic parameters were analyzed by non-compartmental model. Albendazole did not change the pharmacokinetic profiles of marbofloxacin in healthy and diseased lambs. However, M. haemolytica affected the pharmacokinetics of marbofloxacin in diseased lambs, AUC0-24/MIC90 ratio was not found to be higher than 125, but Cmax/MIC90 ratios was found to be higher than 10 for an MIC value of 0.25&nbsp;&mu;g/mL in all groups. The marbofloxacin dose described in this study may not be effective for the treatment of infections due to M. haemolytica in lambs, with MIC &le;&thinsp;0.25&nbsp;&mu;g/mL.<br />
DOI: 10.1007/s11250-019-01980-5 PMID: 31230255<br />
<br />
[3]. Acta Crystallogr Sect E Struct Rep Online. 2012 Apr 1;68(Pt 4):o998-9. doi: 10.1107/S1600536812009312. Epub 2012 Mar 10.<br />
Marbofloxacin.<br />
Shen J, Qian JJ, Gu JM, Hu XR.<br />
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)&deg;. 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) &Aring; 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.<br />
DOI: 10.1107/S1600536812009312 PMCID: PMC3343966 PMID: 22590047<br />
<br />
[4]. J Vet Med Sci. 2019 May 31;81(5):730-733. doi: 10.1292/jvms.18-0761. Epub 2019 Mar 26.<br />
Distribution of marbofloxacin in the bronchoalveolar region in healthy calves.<br />
Hayashi J(1)(2), Otomaru K(2)(3), Hirata M(3), Ishikawa S(2)(3), Ikedo T(3), Horinouchi C(3), Kuramae T(2)(4), Tsumagari K(2)(5), Hobo S(2)(3).<br />
Author information: (1)Miyazaki Agricultural Mutual Aid Association, 280 Takasu, Miyazaki 880-0852, Japan. (2)United Graduate School of Veterinary Sciences, Yamaguchi University, 1677-1, Yoshida, Yamaguchi 753-8511, Japan. (3)Joint Faculty of Veterinary Medicine, Kagoshima University, 1-21-24 Korimoto, Kagoshima 890-0065, Japan. (4)Kuramae Animal Clinic, 3209-2 Koba, Yuhsui, Kagoshima 899-6201, Japan. (5)Soo Agricultural Mutual Aid Association, 2253 Tsukino, Oosumi-cho, Soo-shi, Kagoshima 899-8212, Japan.<br />
The purpose of this study was to clarify the distribution of marbofloxacin (MBFX) within the bronchoalveolar region of calves. Four clinically healthy calves were intramuscularly injected with a single dose of MBFX (2 mg/kg). Samples of plasma and bronchoalveolar lavage fluid (BALF) were obtained for each calf at 0 (before administration), 1, 2, 6 and 24 hr after injection of MBFX. The injections and series of sample collections were conducted and repeated again after two weeks. The results show that the MBFX concentrations in the pulmonary epithelial lining fluid (ELF) were significantly higher than that in plasma and in alveolar cells at 2 hr after injection (P&lt;0.05). For concentrations of MBFX within the ELF, the mean area under the MBFX concentration curve calculated during the 0 to 24 hr timeframe (AUC0-24) was significantly higher than the mean determined from samples collected from the plasma (P&lt;0.05). These results suggest that intramuscularly injected MBFX was well distributed in the bronchoalveolar region.<br />
DOI: 10.1292/jvms.18-0761 PMCID: PMC6541841 PMID: 30918227<br />
<br />
[5]. Vet Rec. 2017 Jun 17;180(24):588-590. doi: 10.1136/vr.j2747.<br />
Is marbofloxacin a good candidate for treating pigs in Europe?<br />
Silva N(1), Sousa M(2).<br />
Author information: (1)Moredun Research Institute, Pentlands Science Park, Bush Loan, Penicuik, Scotland, UK. (2)Veterinary and Animal Science Research Center, University of Tr&aacute;s-os-Montes and Alto Douro, Vila Real, Portugal.<br />
Comment in Vet Rec. 2017 Jul 1;181(1):23. Vet Rec. 2017 Jul 1;181(1):23.<br />
Comment on Vet Rec. 2017 Jun 17;180(24):591.<br />
DOI: 10.1136/vr.j2747 PMID: 28623213

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