(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 ID: 1008
• Molecular Formular: C18H20FN3O4
• Molecular Mass: 361.3675032
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: levofloxacin
• Brand Name: Cravit; Cravit Ophthalmic; Elequine; Floxel; Iquix; Leroxacin; Lesacin; Levaquin; Levokacin; Levox; Levoxacin; Mosardal; Nofaxin; Quixin; Reskuin; Tavanic; Volequin
• Synonyms: (-)-(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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.4470572
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.616237
• LogD (pH = 7.4): -0.2825112
• Log P: 0.65427977
• Molar Refractivity: 94.9359 cm^3
• Polarizability: 34.82272 Å^3
• Polar Surface Area: 73.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.02
• LOG S: -2.4
• Solubility (Water): 1.44e+00 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 214-216°C
• Hydrophobicity(logP): 2.1

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: UU8815550
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-22-42/43-64
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H317-H334-H361d-H362
• GHS Precautionary statements: P261-P263-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Gene Information: human ... KCNH1(3756)

Product Information

• Purity: ≥98.0% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H20FN3O4

DETAILS

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.

REFERENCES

• 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)