(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

• ChemBase编号: 1008
• 分子式: C18H20FN3O4
• 平均质量: 361.3675032
• 单一同位素质量: 361.14378436
• SMILES: Fc1c(N2CCN(CC2)C)c2OC[C@@H](n3c2c(c1)c(=O)c(c3)C(=O)O)C
• Canonical SMILES: CN1CCN(CC1)c1c(F)cc2c3c1OC[C@@H](n3cc(c2=O)C(=O)O)C
• InChI: InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1
• InChIKey: GSDSWSVVBLHKDQ-JTQLQIEISA-N

名称和登记号

名称

• IUPAC标准名: (2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid; (2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• IUPAC传统名: levofloxacin
• 商标名: Cravit; Cravit Ophthalmic; Elequine; Floxel; Iquix; Leroxacin; Lesacin; Levaquin; Levokacin; Levox; Levoxacin; Mosardal; Nofaxin; Quixin; Reskuin; Tavanic; Volequin
• 别名: (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid Hemihydrate; Dynaquin; Levofloxacin Hydrate; Levofloxacin Hemihydrate; (-)-Ofloxacin; Levofloxacin; L-Ofloxacin; levofloxacin; Levofloxacin; Levaquin; Tavanic

登记号

• CAS号: 100986-85-4; 138199-71-0
• MDL号: MFCD00865049
• Beilstein号: 7327015
• PubChem SID: 160964471; 24857060; 46505134
• PubChem CID: 149096

理论计算性质

JChem

• Acid pKa: 5.4470572
• 质子受体: 7
• 质子供体: 1
• LogD (pH = 5.5): 0.616237
• LogD (pH = 7.4): -0.2825112
• Log P: 0.65427977
• 摩尔折射率: 94.9359 cm^3
• 极化性: 34.82272 Å^3
• 极化表面积: 73.32 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.02
• LOG S: -2.4
• 溶解度: 1.44e+00 g/l

分子性质

理化性质

• 溶解度: Insoluble; Methanol
• 外观: Pale Yellow Solid
• 熔点: 214-216°C
• 疏水性(logP): 2.1

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: UU8815550
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 63-22-42/43-64
• 安全公开号: 26-36/37/39
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H317-H334-H361d-H362
• GHS警示性声明: P261-P263-P280-P342 + P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

药理学性质

• 相关基因信息: human ... KCNH1(3756)

产品相关信息

• 纯度: ≥98.0% (HPLC)
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C18H20FN3O4

详细说明

DrugBank - DB01137

• Drug Groups: approved; investigational
• Description: A synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. [PubChem]
• Indication: For the treatment of bacterial conjunctivitis caused by susceptible strains of the following organisms: Corynebacterium species, Staphylococus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, Streptococcus (Groups C/F/G), Viridans group streptococci, Acinetobacter lwoffii, Haemophilus influenzae, Serratia marcescens.
• Pharmacology: Levofloxacin, a fluoroquinolone antiinfective, is the optically active L-isomer of ofloxacin. Levofloxacin is used to treat bacterial conjunctivitis, sinusitis, chronic bronchitis, community-acquired pneumonia and pneumonia caused by penicillin-resistant strains of Streptococcus pneumoniae, skin and skin structure infections, complicated urinary tract infections and acute pyelonephritis.
• Toxicity: Side effects include disorientation, dizziness, drowsiness, hot and cold flashes, nausea, slurring of speech, swelling and numbness in the face
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Mainly excreted as unchanged drug (87%); undergoes limited metabolism in humans.
• Absorption: Absorption of ofloxacin after single or multiple doses of 200 to 400 mg is predictable, and the amount of drug absorbed increases proportionately with the dose.
• Half Life: 6-8 hours
• Protein Binding: 24-38% (to plasma proteins)
• Elimination: Mainly excreted as unchanged drug in the urine.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1940

Research Area: Infection
Biological Activity:
Levofloxacin(Levaquin) is a synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. Levofloxacin inhibits bacterial type II topoisomerases, topoisomerase IV and DNA gyrase. Levofloxacin, like other fluoroquinolones, inhibits the A subunits of DNA gyrase, two subunits encoded by the gyrA gene. This results in strand breakage on a bacterial chromosome, supercoiling, and resealing; DNA replication and transcription is inhibited. [1]

Sigma Aldrich - 28266

Other Notes
Antibiotic against bacterial respiratory tract infections5,6
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 28266.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Application
Levofloxacin is a broad-spectrum antibiotic used in pharmacokinetic 1, antibiotic resistance 2 , and resistance prevention 3studies.
Biochem/physiol Actions
Levofloxacin is active against Gram-positive and Gram-negative bacteria. It inhibits DNA gyrase (type II topoisomerase) and topoisomerase IV, 4 thereby inhibiting cell division.

Toronto Research Chemicals - L360000

S-(-)-Form of Ofloxacin. An antibiotic used against gram-negative organisms.

参考文献

• http://www.drugbank.ca/drugs/DB01137
• Kato, M., et al.: Arzneim.-Forsch., 42, 365 (1992)
• North, D.S., et al.: Pharmacotherapy, 18, 915 (1992)
• Hwang, D.G., et al.: Br. J. Ophthalmol., 87, 1004 (1992)