105394-83-0

Basic information

• Product Name: Decarboxy Ciprofloxacin
• Synonyms: 1-Cyclopropyl-6-fluoro-7-(1-piperazinyl)-4(1H)-quinolinone;Decarboxy Ciprofloxacin;Ciprofloxacin IMpurity E(EP);Ciprofloxacin EP IMpurity E;1-Cyclopropyl-6-fluoro-7-(piperazin-1-yl)quinolin-4(1H)-one
• CAS NO: 105394-83-0
• Molecular Formula: C16H18FN3O
• Molecular Weight: 287.33
• Product Categories: Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 105394-83-0.mol

Chemical Properties

• Melting Point: 196-198°C
• Boiling Point: 496.641°C at 760 mmHg
• Flash Point: 254.159°C
• Appearance: /
• Density: 1.327g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.631
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.68±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Decarboxy Ciprofloxacin(CAS DataBase Reference)
• NIST Chemistry Reference: Decarboxy Ciprofloxacin(105394-83-0)
• EPA Substance Registry System: Decarboxy Ciprofloxacin(105394-83-0)

Safety Data

• Hazardous Substances Data: 105394-83-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Decarboxy Ciprofloxacin is used as a reference material for the identification and quantification of impurities in the synthesis process of Ciprofloxacin. This helps ensure the quality and purity of the final antibiotic product.
Used in Research and Development:
Decarboxy Ciprofloxacin is used as a research compound for studying the chemical properties and behavior of Ciprofloxacin impurities. This can aid in the development of improved synthesis methods and the reduction of impurities in the final product.
Used in Quality Control:
Decarboxy Ciprofloxacin is used as a reference standard in quality control testing of Ciprofloxacin products. It helps to establish the acceptable limits of impurities in the final drug, ensuring patient safety and the efficacy of the medication.
Used in Analytical Method Development:
Decarboxy Ciprofloxacin is used in the development and validation of analytical methods for the detection and quantification of impurities in Ciprofloxacin. This is crucial for maintaining the quality and consistency of the antibiotic in the pharmaceutical market.

InChI:InChI=1/C16H18FN3O/c17-13-9-12-14(10-15(13)19-7-4-18-5-8-19)20(11-1-2-11)6-3-16(12)21/h3,6,9-11,18H,1-2,4-5,7-8H2

Upstream product

• 85721-33-1 ciprofloxacin 
• 1337918-18-9 7-(4-formylpiperazin-1-yl)-1-cyclopropyl-6-fluoroquinolin-4-one 
• 93107-08-5 ciprofloxacin hydrochloride 

Relevant articles and documents

Synthesis and biological evaluation of 6-fluoro-3-phenyl-7-piperazinyl quinolone derivatives as potential topoisomerase I inhibitors

The design and synthesis of a new series of 6-fluoro-3-phenyl-7-piperazinyl quinolone derivatives, built on the structure of 1-ethyl-3-(6-nitrobenzoxazol-2-yl)-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4(1H)-quinolone, are described. These compounds provide

Preparation and antibacterial evaluation of decarboxylated fluoroquinolones

Decarboxylated ciprofloxacin (3) has been reported in the literature to have antibacterial activities against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Bacillus subtilis, Enterobacter cloacae, Serratia marcescens and especially potent activity against Escherichia coli. Herein, we report our syntheses of 3 and five additional decarboxylated fluoroquinolones (FQs). We have re-evaluated the antibacterial activity of these FQs. In contrast to previously reported data, none of these decarboxylated fluoroquinolones showed significant antibacterial activity in our assays using both the broth dilution and agar methods. Our study confirmed that the presence of a carboxylic acid group at the 3-position of the fluoroquinolone scaffold is essential for antibacterial activity.

Synthesis and evaluation of 1-cyclopropyl-2-thioalkyl-8-methoxy fluoroquinolones

Novel fluoroquinolone derivatives substituted with a 2-thioalkyl moiety, with and without a concomitant 3-carboxylate group, were synthesized to evaluate the effect of C-2 thioalkyl substituents on gyrase binding and inhibition. The presence of a 2-thioalkyl group universally decreased activity as compared to parent fluoroquinolones. However, with derivatives of moxifloxacin the presence of either a 2-thioalkyl group or a 3-carboxylate moiety increased activity over the 2,3-unsubstituted derivative. Energy minimization of structures provides an explanation for relative activities of fluoroquinolones having a C-2 thio moiety.

Quinolin-4-one derivatives and their use as antibiotics

The compound having the general formula (I) whereinX is selected from the group consisting of oxygen, sulfur and nitrogen-containing groups selected from azine, oxime, hydrazone, aromatic hydrazone, aliphatic hydrazone, semicarbazone, guanidinyl group, or aliphatic or aromatic imines;Y is selected fron the group of halogens;R1 and R2 are independently selected from the group consisting of H, lower alkyl group (of C1 up to C6), lower hydroxyalkyl group (of C1 up to C6), lower O-alkyl group (of C1 up to C6), lower alkylcarbonyl group (of C1 up to C6), lower alkyloxycarbonyl group (of C1 up to C6), haloalkylcarbonyl group (of C1 up to C6), or arylsulfonyl group,and their pharmaceutically acceptable salts, are useful as active ingredients in pharmaceutical compositions. The invention relates to the use of the said compounds as a medicament, in particular as an antibiotic.

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

Cyanide mediated decarboxylation of 1-substituted-4-oxoquinoline and 4-oxo-1,8-naphthyridine-3-carboxylic acids

Electron deficient 3-quinolinecarboxylic acids undergo ready decarboxylation in the presence of cyanide ion. This reaction most likely requires the addition of CN- to the 2-position of the quinoline (or naphthyridine) nucleus to provide a β-keto acid intermediate that rapidly decarboxylates to give the 3-H substituted product.