103222-12-4

Basic information

• Product Name: DESETHYLENE CIPROFLOXACIN
• Synonyms: DESETHYLENE CIPROFLOXACIN;ciprofloxacin-7-ethylenediamine;1-Cyclopropyl-4-oxo-6-fluoro-7-(2-aminoethylamino)-1,4-dihydro-3-quinolinecarboxylic acid;1-Cyclopropyl-4-oxo-6-fluoro-7-[(2-aminoethyl)amino]-1,4-dihydro-3-quinolinecarboxylic acid;1-Cyclopropyl-4-oxo-6-fluoro-7-[(2-aminoethyl)amino]-1,4-dihydroquinoline-3-carboxylic acid;1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[(2-aminoethyl)amino]-3-quinolinecarboxylic acid;M1-Ciprofloxacin;3-Quinolinecarboxylic acid, 7-[(2-aMinoethyl)aMino]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-
• CAS NO: 103222-12-4
• Molecular Formula: C₁₅H₁₆FN₃O₃
• Molecular Weight: 305.3
• Mol File: 103222-12-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 550.2°Cat760mmHg
• Flash Point: 286.5°C
• Appearance: /
• Density: 1.541g/cm³
• Vapor Pressure: 6.13E-13mmHg at 25°C
• Refractive Index: 1.71
• PKA: 6.40±0.41(Predicted)
• CAS DataBase Reference: DESETHYLENE CIPROFLOXACIN(CAS DataBase Reference)
• NIST Chemistry Reference: DESETHYLENE CIPROFLOXACIN(103222-12-4)
• EPA Substance Registry System: DESETHYLENE CIPROFLOXACIN(103222-12-4)

Safety Data

• Hazardous Substances Data: 103222-12-4(Hazardous Substances Data)

Usage

General Description

Desethylene ciprofloxacin is a metabolite of the antibiotic ciprofloxacin, which is commonly used to treat bacterial infections. It is produced when the body breaks down ciprofloxacin, and is excreted in the urine. Desethylene ciprofloxacin has some antibacterial activity, but its concentration in the body is much lower than that of its parent compound. It is also known to have a longer half-life in the body, which means it may linger in the system for a longer period of time. Overall, desethylene ciprofloxacin is an important component to consider in the pharmacokinetics and pharmacodynamics of ciprofloxacin, as it may contribute to the overall effectiveness and safety of the drug.

InChI:InChI=1/C15H16FN3O3/c16-11-5-9-13(6-12(11)18-4-3-17)19(8-1-2-8)7-10(14(9)20)15(21)22/h5-8,18H,1-4,17H2,(H,21,22)

Upstream product

• 864443-44-7 N-nitrosociprofloxacin 
• 85721-33-1 ciprofloxacin 
• 93107-30-3 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 93107-08-5 ciprofloxacin hydrochloride 
• 86393-33-1 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 
• 107-15-3 ethylenediamine 

Relevant articles and documents

Synthesis and antibacterial evaluation of novel 4′-glycyl linked quinolyl-azithromycins with potent activity against macrolide-resistant pathogens

A new azithromycin-based series of antibacterial macrolones is reported, which features the use of a 4′-ester linked glycin for tethering the quinolone side chain to the macrolide scaffold. Among the analogs prepared, compounds 9e and 22f with a quinolon-6-yl moiety were found to have potent and well-balanced activity against clinically important respiratory tract pathogens, including erythromycin-susceptible and MLSB resistant strains of Streptococcus pneumoniae, Streptococcus pyogenes, and Haemophilus influenzae. In addition, potential lead compounds 9e and 22f demonstrated outstanding levels of activity against Moraxella catarrhalis and inducibly MLSB resistant Staphylococcus aureus. The best member of this series 22f rivals or exceeds, in potency, some of the most active ketolide antibacterial agents known today, such as telithromycin and cethromycin.

Nitric oxide reactivity accounts for N-nitroso-ciprofloxacin formation under nitrate-reducing conditions

The formation of N-nitroso-ciprofloxacin (CIP) was investigated both in wastewater treatment plants including nitrification/denitrification stages and in sludge slurry experiments under denitrifying conditions. The analysis of biological wastewater treatment plant effluents by Kendrick mass defect analysis and liquid chromatography - high resolution - mass spectrometry (LC[sbnd]HRMS) revealed the occurrence of N-nitroso-CIP and N-nitroso-hydrochlorothiazide at concentration levels of 34 ± 3 ng/L and 71 ± 6 ng/L, respectively. In laboratory experiments and dark conditions, produced N-nitroso-CIP concentrations reached a plateau during the course of biodegradation experiments. A mass balance was achieved after identification and quantification of several transformation products by LC[sbnd]HRMS. N-nitroso-CIP accounted for 14.3% of the initial CIP concentration (20 μg/L) and accumulated against time. The use of 4,5-diaminofluorescein diacetate and superoxide dismutase as scavengers for in situ production of nitric oxide and superoxide radical anion respectively, revealed that the mechanisms of formation of N-nitroso-CIP likely involved a nitrosation pathway through the formation of peroxynitrite and another one through codenitrification processes, even though the former one appeared to be prevalent. This work extended the possible sources of N-nitrosamines by including a formation pathway relying on nitric oxide reactivity with secondary amines under activated sludge treatment.

Photochemistry of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)quinoline-3- carboxylic acid (=ciprofloxacin) in aqueous solutions

The 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)quinoline-3- carboxylic acid (=ciprofloxacin; 1) undergoes low-efficiency (φ=0.07) substitution of the 6-fluoro by an OH group on irradiation in H2O via the ππ* triplet (detected by