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编号: 72692
• 分子式: C17H19FN4O4
• 平均质量: 362.3555632
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: marbofloxacin
• 别名: 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; 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

登记号

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

理论计算性质

• Acid pKa: 5.3832912
• 质子受体: 8
• 质子供体: 1
• LogD (pH = 5.5): -0.05690329
• LogD (pH = 7.4): -1.0131361
• Log P: -0.045496024
• 摩尔折射率: 103.0193 cm^3
• 极化性: 34.429314 Å^3
• 极化表面积: 76.56 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; DMF
• 外观: Pale Yellow Solid
• 熔点: 278-281°C (dec.)

安全信息

• 保存条件: -20°C; -20°C Freezer, Under Inert Atmosphere
• RTECS编号: UU8815140
• 德国WGK号: 2
• 危险公开号: 52/53
• 个人保护装置: Gloves

产品相关信息

• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C17H19FN4O4

详细说明

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

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC
Zeniquin 注册商标 Pfizer, Inc.

Toronto Research Chemicals - M197000

Fluorinated quinolone antibacterial.

参考文献

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