86393-33-1

Basic information

• Product Name: 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• Synonyms: TIMTEC-BB SBB003016;1-CYCLOPROPYL-7-CHLORO-6-FLUORO-1,4-DIHYDRO-4-OXOQUINOLONE-3-CARBOXYLIC ACID;1-CYCLOPROPYL-6-FLUORO-7-CHLORO-1,4-DIHYDRO-4-OXO-3-QUINOLINIC CARBOXYLIC ACID;7-CHLORO-1-CYCLOPROPYL-1,4-DIHYDRO-6-FLUOROQUINOL-4-ONE-3-CARBOXYLIC ACID;7-CHLORO-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID;7-CHLORO-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID;7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID;7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXOHYDROQUINOLINE-3-CARBOXYLIC ACID
• CAS NO: 86393-33-1
• Molecular Formula: C₁₃H₉ClFNO₃
• Molecular Weight: 281.67
• EINECS: 405-050-0
• Product Categories: Ciprofloxacin;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycles;Metabolites & Impurities;alkyl chloride | alkyl Fluorine| carboxylic acid;Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 86393-33-1.mol
• Article Data: 17

Chemical Properties

• Melting Point: 242-245 °C(lit.)
• Boiling Point: 467.3 °C at 760 mmHg
• Flash Point: 236.4 °C
• Appearance: off-white crystalline powder
• Density: 1.652±0.06 g/cm3(Predicted)
• Vapor Pressure: 1.56E-09mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 6.36±0.41(Predicted)
• CAS DataBase Reference: 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid(86393-33-1)
• EPA Substance Registry System: 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid(86393-33-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-52/53
• Safety Statements: 26-36-61-22
• WGK Germany: 2
• RTECS: VB1993795
• HazardClass: IRRITANT
• Hazardous Substances Data: 86393-33-1(Hazardous Substances Data)

Usage

Description

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid is a chemical compound that serves as an intermediate and a metabolite in the synthesis and metabolism of Ciprofloxacin, a fluorinated quinolone antibacterial agent.

Uses

Used in Pharmaceutical Industry:
7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid is used as an intermediate in the synthesis of Ciprofloxacin, a fluorinated quinolone antibacterial. It plays a crucial role in the production process of this widely used antibiotic medication.
Used in Metabolism Studies:
As a metabolite of Ciprofloxacin, 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid is utilized in research and studies to understand the metabolic pathways and pharmacokinetics of the antibiotic, contributing to the optimization of its therapeutic use and potential improvements in drug design.
Used in Quality Control:
7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic Acid (Ciprofloxacin EP Impurity A) is recognized as a metabolite of Ciprofloxacin and is used in quality control processes to ensure the purity and efficacy of the final antibiotic product. This helps maintain the safety and effectiveness of Ciprofloxacin as a fluorinated quinolone antibacterial.

InChI:InChI=1/C13H9ClFNO3/c14-9-4-11-7(3-10(9)15)12(17)8(13(18)19)5-16(11)6-1-2-6/h3-6H,1-2H2,(H,18,19)/p-1

Upstream product

• 86483-54-7 ethyl 1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate 
• 104599-90-8 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid methyl ester 
• 704-10-9 2,4-dichloro-5-fluoroacetophenone 
• 104600-21-7 methyl 3-cyclopropylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylate 
• 104600-30-8 ethyl 2-(2,4-dichloro-5-fluoro-benzoyl)-3-cyclopropylamino-acrylate 
• 86483-51-4 ethyl 2,4-dichloro-5-fluoro-benzoyl-acetate 
• 86483-53-6 3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-ethylester 
• 86393-34-2 2,4-dichloro-5-fluorobenzoyl chloride 
• 105392-26-5 3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-methylester 
• 86483-50-3 diethyl 2,4-dichloro-5-fluoro-benzoyl-malonate 
• 72396-25-9 N-(Cyclopropylamino)acrylsaeure-methylester 
• 86483-52-5 2,4-dichloro-alpha(elhoxymethlene)-5-fluoro-beta-oxo-benzene propanoic acid ethyl ester 
• 110600-98-1 ethyl 7-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 110600-97-0 ethyl 1-cyclopropyl-6-fluoro-1,4-dihydro-7-nitro-4-oxoquinoline-3-carboxylate 

Downstream Products

• 85721-33-1 ciprofloxacin 
• 93106-60-6 enrofloxacin 
• 133210-96-5 1-cyclopropyl-7-chloro-6-piperazinyl-4-oxo-1,2-dihydroquinoline-3-carboxylic acid 
• 104599-90-8 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid methyl ester 
• 444335-12-0 7-(4-{4-[(S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 526204-10-4 7-chloro-1-cyclopropyl-4-oxo-6-piperazin-1-yl-1,4-dihydro-quinoline-3-carboxylic acid; hydrochloride 
• 93107-08-5 ciprofloxacin hydrochloride 
• 929904-12-1 C₁₉H₁₄O₂N₂ClF 
• 929904-13-2 C₂₀H₁₆O₂N₂ClF 
• 929904-14-3 C₂₀H₁₆O₂N₂ClF 
• 929904-15-4 C₂₀H₁₆O₂N₂ClF 
• 929904-16-5 C₂₀H₁₆O₃N₂ClF 
• 929904-17-6 C₂₀H₁₆O₃N₂ClF 
• 929904-18-7 C₁₉H₁₃O₂N₂Cl₂F 

Relevant articles and documents

An operational transformation of 3-carboxy-4-quinolones into 3-nitro-4-quinolones via ipso-nitration using polysaccharide supported copper nanoparticles: Synthesis of 3-tetrazolyl bioisosteres of 3-carboxy-4-quinolones as antibacterial agents

Chitosan supported Cu nano-particles have been synthesized, and utilized for the synthesis of 3-nitro-4-quinolones from 3-carboxy-4-quinolones via ipso nitration. The synthesized 3-nitro derivatives of 4-quinolones were successfully converted into their 3-tetrazolyl bioisosteres which showed increased antibacterial activity as compared to the standard ciprofloxacin.

Synthesis, characterization and biological studies of some homodinuclear complexes of zinc with second-generation quinolone drug and neutral bidentate ligands

The novel homodinuclear zinc(II) complexes with the quinolone antibacterial drugs ciprofloxacine and neutral bidentate ligands have been synthesized and characterized by elemental analysis, TG analyses and various spectroscopic techniques. The metal ion exhibits octahedral geometry with two water molecule in the inner sphere cavity environment. The interaction of complexes with DNA was determined using absorption titration, viscosity measurements and electrophoresis technique. The intrinsic binding constants (Kb) of complexes were determined, which were ranging from 1.0 × 104 to 3.5 × 104 per mole. Suggesting that complexes bind more strongly to DNA. Effect on viscosity has also been checked to authenticate the binding of metal complexes with DNA. An antimicrobial activity of all the ligands and metal complexes has been examined by minimum inhibitory concentration method (MIC).

Compounds with antibacterial and antiparasitic properties

There are provided novel compounds which have both antibacterial and antiparasitic properties, thereby reducing the need for using several compounds in combined antibacterial and antiparasitic treatment of livestock. The present novel compounds are especially well suited for treatment of coccidiosis, and they are represented by general formula (I) wherein R1-R6, X and A are as defined in the specification.