93594-39-9

Basic information

• Product Name: FORMYLCIPROFLOXACIN
• Synonyms: FORMYLCIPROFLOXACIN;Formylciprofloxacin(M4);1-Cyclopropyl-4-oxo-6-fluoro-7-(4-formyl-1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid;1-Cyclopropyl-4-oxo-6-fluoro-7-(4-formylpiperazino)-1,4-dihydroquinoline-3-carboxylic acid;1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-formylpiperazino)-3-quinolinecarboxylic acid;6-Fluoro-1-cyclopropyl-1,4-dihydro-4-oxo-7-(4-formylpiperazino)quinoline-3-carboxylic acid;N-Formylciprofloxacin;Ciprofloxacin Formamide (125 mg)
• CAS NO: 93594-39-9
• Molecular Formula: C18H18FN3O4
• Molecular Weight: 359.35
• Product Categories: Various Metabolites and Impurities;Metabolites
• Mol File: 93594-39-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: >280°C (dec.)
• Boiling Point: 648oC at 760 mmHg
• Flash Point: 345.7oC
• Appearance: /
• Density: 1.573g/cm3
• Vapor Pressure: 1.12E-17mmHg at 25°C
• Refractive Index: 1.718
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly, Heated, Sonicated), Methanol (Sparingly), Water (Sparingly)
• PKA: 6.44±0.41(Predicted)
• CAS DataBase Reference: FORMYLCIPROFLOXACIN(CAS DataBase Reference)
• NIST Chemistry Reference: FORMYLCIPROFLOXACIN(93594-39-9)
• EPA Substance Registry System: FORMYLCIPROFLOXACIN(93594-39-9)

Safety Data

• Hazardous Substances Data: 93594-39-9(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

InChI:InChI=1/C18H18FN3O4/c19-14-7-12-15(8-16(14)21-5-3-20(10-23)4-6-21)22(11-1-2-11)9-13(17(12)24)18(25)26/h7-11H,1-6H2,(H,25,26)

Upstream product

• 1340587-05-4 1-cyclopropyl-6-fluoro-4-oxo-7-(4-((2-(4-fluorobenzoyl)hydrazono)methyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid 
• 64-18-6 formic acid 
• 85721-33-1 ciprofloxacin 
• 68-12-2 N,N-dimethyl-formamide 
• 93107-08-5 ciprofloxacin hydrochloride 

Downstream Products

• 1616781-05-5 1-cyclopropyl-6-fluoro-7-(4-(3-(6-fluorobenzo[d]thiazol-2-yl)-4-oxothiazolidin-2-yl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1616780-91-6 C₂₅H₂₁F₂N₅O₃S 
• 1616780-94-9 C₂₆H₂₁FN₆O₃S 
• 1616781-08-8 C₂₈H₂₃FN₆O₄S₂ 

Relevant articles and documents

Synthesis of ciprofloxacin dimers for evaluation of bacterial permeability in atypical chemical space

Abstract We describe the synthesis and evaluation of a library of variably-linked ciprofloxacin dimers. These structures unify and expand on the use of fluoroquinolones as probes throughout the antibiotic literature. A dimeric analog (19) showed enhanced inhibition of its intracellular target (DNA gyrase), and translation to antibacterial activity in whole cells was demonstrated. Overall, cell permeation was governed by physicochemical properties and bacterial type. A principal component analysis demonstrated that the dimers occupy a unique and privileged region of chemical space most similar to the macrolide class of antibiotics.

New fluorine-containing hydrazones active against MDR-tuberculosis

Several new fluorine-containing hydrazones were synthesized and screened for their in vitro antimycobacterial activity. Nine of these derivatives have shown a remarkable activity against MDR-TB strain with MIC 0.5 μg/mL and high value of selectivity index (SI). Compound 3h with the highest SI (1268.58) was used for stability evaluation with putative metabolites (ciprofloxacin and formylciprofloxacin) detection. Compound 3h was stable at pH 7.4 of aqueous buffer and rat plasma, in acidic buffers (at pH 3 and 5) slow decomposition was observed. Interestingly, no formylciprofloxacin was detected in the solution, and only slightly increased concentration of ciprofloxacin was observed instead. Trifluoromethyl hydrazones 3f and 3g exhibited the best activity also against two strains of Mycobacterium kansasii (MIC 1-4 μmol/L). All evaluated compounds were found to be non-cytotoxic.

Isolation and structural elucidation of urinary metabolites of ciprofloxacin

After oral administration of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazine-1-ylqu inoline-3-carboxylic acid (ciprofloxacin, Bay o 9867; designated trademark: Ciprobay) four metabolites M1-M4 were isolated from human urine by Craig counter current distribution and semipreparative high-performance liquid chromatography. Their molecular structures were elucidated by nuclear magnetic resonance and mass spectrometry and confirmed by comparing their spectra with those of authentic synthetic reference compounds.