7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid

• ChemBase ID: 105015
• Molecular Formular: C14H12FNO3
• Molecular Mass: 261.2483832
• Monoisotopic Mass: 261.08012147
• SMILES: CC1CCc2cc(F)cc3c2n1cc(C(=O)O)c3=O
• Canonical SMILES: Fc1cc2CCC(n3c2c(c1)c(=O)c(c3)C(=O)O)C
• InChI: InChI=1S/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19)
• InChIKey: DPSPPJIUMHPXMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0^5,^1^3]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid; 7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0^{5,13}]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid
• IUPAC Traditional name: flumequine
• Synonyms: 9-Fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic Acid; Apurone; Fantacin; R 802; Flumequine; FLUMEQUINE; 氟甲喹

Database IDs

• CAS Number: 42835-25-6
• EC Number: 255-962-6
• MDL Number: MFCD00079298
• Beilstein Number: 490724
• PubChem SID: 24894926; 24869307; 162093308
• PubChem CID: 3374

CALCULATED PROPERTIES

• Acid pKa: 6.0047708
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.29869
• LogD (pH = 7.4): 1.0076491
• Log P: 2.4168396
• Molar Refractivity: 67.8736 cm^3
• Polarizability: 24.735838 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 253-255°C; 260-262°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others

Product Information

• Grade: PESTANAL®, analytical standard
• Salt Data: Free Base
• Suitability: suitable for 1694 per US EPA
• Empirical Formula (Hill Notation): C14H12FNO3

DETAILS

Sigma Aldrich - F7016

Application
Flumequine is a fluoroquinolone synthetic chemotherapeutic antibiotic. Flumequine is used to study processes that affect mammalian chromosome and DNA unwinding at the level of gyrase/topoisomerases. It is used to study hepatocarcinogenicity and DNA damage in mice and the mechanisms of quinolone resistance1,2.
Flumequine is used to study processes that affect mammalian chromosome and DNA unwinding at the level of gyrase/topoisomerases.
Biochem/physiol Actions
Flumequine inhibits topoisomerases, which are needed for the transcription and replication of bacterial DNA. The inhibition of the topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. Therefore, DNA replication and transcription is inhibited .

Sigma Aldrich - 45735

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - F445000

Fluorinated quinolone antibacterial.

REFERENCES

• Stilwell, G., et al.: Antimicrob. Agents Chemother., 7, 483 (1975)
• Rohlfing, S.R., et al.: J. Antimicrob. Chemother., 3, 615 (1975)