7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1,2-diazatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

• ChemBase ID: 72692
• Molecular Formular: C17H19FN4O4
• Molecular Mass: 362.3555632
• Monoisotopic Mass: 362.13903333
• SMILES: c1(c(c2c3c(c1)c(=O)c(cn3N(CO2)C)C(=O)O)N1CCN(CC1)C)F
• Canonical SMILES: CN1CCN(CC1)c1c(F)cc2c3c1OCN(n3cc(c2=O)C(=O)O)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1,2-diazatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid; 7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1,2-diazatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• IUPAC Traditional name: marbofloxacin
• 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; Marbofloxacin; Zeniquin®; 9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-piperazino)-7-oxo-7H-pyrido[1,2,3-ij][1,2,4]benzoxadiazine-6-carboxylic acid; Marbofloxacin; 9-氟代-2,3-二氢-3-甲基-10-(4-甲基-哌嗪)-7-氧代-7H-吡啶并[1,2,3-ij][1,2,4]苯并噁二嗪-6-羧酸; 麻保沙星

Database IDs

• CAS Number: 115550-35-1
• MDL Number: MFCD00864820
• PubChem SID: 162037613; 24860807
• PubChem CID: 60651

CALCULATED PROPERTIES

• Acid pKa: 5.3832912
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -0.05690329
• LogD (pH = 7.4): -1.0131361
• Log P: -0.045496024
• Molar Refractivity: 103.0193 cm^3
• Polarizability: 34.429314 Å^3
• Polar Surface Area: 76.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMF
• Apperance: Pale Yellow Solid
• Melting Point: 278-281°C (dec.)

Safety Information

• Storage Condition: -20°C; -20°C Freezer, Under Inert Atmosphere
• RTECS: UU8815140
• German water hazard class: 2
• Risk Statements: 52/53
• Personal Protective Equipment: Gloves

Product Information

• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C17H19FN4O4

DETAILS

Selleck Chemicals - S1464

Research Area

• Description: Infection

Biological Activity

• Description: Marbofloxacin is a potent antibiotic inhibiting bacterial DNA replication.
• In Vitro: Marbofloxacin is a fluoroquinolone antimicrobial agent developed exclusively for veterinary use. Marbofloxacin exhibits high bactericidal activity against a broad spectrum of aerobic Gram-negative and some Gram-positive bacteria, as well as Mycoplasma spp. As the third generation fluoroquinolone, Marbofloxacin also mainly targets replication and transcription enzymes such as DNA gyrase and topoisomerase IV, which are both essential for bacterial viability. Marbofloxacin has a mycoplasmacidal effect during the exponential phase but not during the lag phase, in both the M. hyopneumoniae 116 wild-type strain and a clone isolated 4 days post-marbofloxacin treatment in vivo at the therapeutic dose. ^[1] Marbofloxacin significantly kills Leishmania promastigotes and intracellular amastigotes in a dose-dependent manner, more efficient than meglumine antimoniate and sodium stibogluconate. After treatment with Marbofloxacin, macrophages acquire resistance to infection and enhanced antileishmanial activity through the NO synthase pathway. ^[2]
• In Vivo: Marbofloxacin treatment at the therapeutic dose does not eliminate M. hyopneumoniae, with 87.5 to 100% of the pigs still positive at the end of the assays, and is not effective in significantly reducing clinical signs. Nevertheless, Marbofloxacin treatment seems to decrease the lung lesion scores. ^[1] Administration of Marbofloxacin at 6 mg/kg once daily for 7 days in a Staphylococcus aureus infection in tissue cages in ponies is not effective for the elimination of S. aureus infections from secluded sites. ^[3]

Protocol

• Protocol: Animal Study ^[1]
• Animal Models: SPF piglets inoculated intratracheally with M. hyopneumoniae strain 116
• Formulation: Dissolved DMSO, and diluted in saline
• Doses: ~2 mg/kg/day
• Administration: Intramuscular injection

References

• References: [1] Le Carrou J, et al. Antimicrob Agents Chemother, 2006, 50(6), 1959-1966.
• References: [2] Vouldoukis I, et al. Vet Parasitol, 2006, 135(2), 137-146.
• References: [3] Voermans M, et al. J Vet Pharmacol Ther, 2006, 29(6), 555-560.

Sigma Aldrich - 34039

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Zeniquin is a registered trademark of Pfizer, Inc.

Toronto Research Chemicals - M197000

Fluorinated quinolone antibacterial.

REFERENCES

• Gruet, P., et al.: Vet. Rec., 140, 199 (1977)
• Lefebvre, H.P., et al.: J. Vet. Pharmacol. Ther., 21, 453 (1977)