1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-ylquinoline-3-carboxylate

Base Information

• Chemical Name: 1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-ylquinoline-3-carboxylate
• CAS No.: 85721-33-1
• Molecular Formula: C17H18F N3 O3
• Molecular Weight: 331.347
• Hs Code.: 29339900
• Mol file: 85721-33-1.mol

Synonyms:1-CFOPI cpd;1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3-carboxylate;Anhydrous, Ciprofloxacin Hydrochloride;Bay 09867;Bay-09867;Bay09867;Ciprinol;Cipro;Ciprofloxacin;Ciprofloxacin Hydrochloride;Ciprofloxacin Hydrochloride Anhydrous;Ciprofloxacin Monohydrochloride Monohydrate;Hydrochloride Anhydrous, Ciprofloxacin;Hydrochloride, Ciprofloxacin;Monohydrate, Ciprofloxacin Monohydrochloride;Monohydrochloride Monohydrate, Ciprofloxacin

Chemical Property of 1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-ylquinoline-3-carboxylate

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 2.24E-14mmHg at 25°C
• Melting Point: 255-257 °C
• Boiling Point: 581.774 °C at 760 mmHg
• PKA: pKa 4.04 (Uncertain)
• Flash Point: 305.646 °C
• PSA: 74.57000
• Density: 1.461 g/cm³
• LogP: 1.97710
• Storage Temp.: Store at 0-5°C
• Solubility.: Soluble in 0.1N HCl at 25mg/ml. Poorly soluble in DMSO
• Water Solubility.: 86mg/L(25 oC)
• XLogP3: -1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 331.13321961
• Heavy Atom Count: 24
• Complexity: 566

Purity/Quality:

99%, ^*data from raw suppliers

Ciprofloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC1N2C=C(C(=O)C3=CC(=C(C=C32)N4CC[NH2+]CC4)F)C(=O)[O-]
• Recent ClinicalTrials: Special Drug Use Investigation of Ciproxan Injection in Pediatrics
• Description: Ciprofloxacin is a quinolone antibacterial related to recently marketed norfloxacin (10), ofloxacin (2), pefloxacin (2) and enoxacin. It has a broad spectrum of activity against gram-positive and gram-negative bacteria, and is useful in the treatment of urinary and upper respiratory tract infections.
• Uses: Ciprofloxacin, inhibits bacterial DNA gyrase (topoisomerase). Inhibits cell division and causes double-strand breaks in the bacterial chromosome. Ciprofloxacin is used in the treatment of infections from a wide range of aerobic gram-positive and aerobic gramnegative microorganisms. It has been shown to be effective against inhalational anthrax and reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. It is also used in select respiratory infections, urinary tract infections, typhoid fever, some sexually transmitted diseases, and septicemia. Infectious diarrhea may be caused by organisms found in food or water and transferred by person-to-person contact. This may have a devastating effect, globally, especially in immunocompromised individuals. Ciprofloxacin is effective against those organisms that may contribute to infectious diarrhea, such as Escherichia coli (enterotoxigenic strains), Campylobacter jejuni, and select strains of Shigella; and is utilized when antibacterial therapy is medically indicated. Ciprofloxacin has also been utilized as a secondary agent in the treatment of tuberculosis.
• Therapeutic Function: Antibiotic
• Clinical Use: Antibacterial agent
• Drug interactions: Potentially hazardous interactions with other drugs Aminophylline and theophylline: possibly increased risk of convulsions; increased levels of aminophylline and theophylline. Analgesics: increased risk of convulsions with NSAIDs. Anticoagulants: anticoagulant effect of coumarins enhanced. Antidepressants: metabolism of duloxetine inhibited - avoid; avoid with agomelatine. Antimalarials: manufacturer of artemether with lumefantrine advises avoid concomitant use. Antipsychotics: possibly increased concentration of olanzapine and clozapine. Ciclosporin: variable response; no interaction seen locally; some reports of increased nephrotoxicity. Clopidogrel: possibly reduced antiplatelet effect. Cytotoxics: possibly increased concentration of bosutinib, ibrutinib and olaparib - avoid or consider reducing dose of bosutinib; possibly reduced excretion of methotrexate; concentration of erlotinib increased. Muscle relaxants: tizanidine concentration increased - avoid. Pirfenidone: concentration of pirfenidone increased - reduce dose of pirfenidone. Tacrolimus: increased levels (anecdotally).

Technology Process of 1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-ylquinoline-3-carboxylate

There total 57 articles about 1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-ylquinoline-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.7%

7-[4-tert-butoxycarbonyl-piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (93594-48-0) → ciprofloxacin (85721-33-1,178489-05-9,189257-90-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

Reference yield: 96.2%

piperazine (110-85-0) + C15H16Cl2FNO3 → ciprofloxacin (85721-33-1,178489-05-9,189257-90-7)

Guidance literature:

With 1-butyl-3-methylimidazolium hydroxide; at 70 ℃; for 5h; Reagent/catalyst; Temperature;

Reference yield: 96.0%

ciprofloxacin hydrochloride (93107-08-5,86483-48-9) → ciprofloxacin (85721-33-1,178489-05-9,189257-90-7)

Guidance literature:

With sodium hydrogencarbonate; In water;

DOI:10.1016/j.ejmech.2016.08.031

upstream raw materials:

piperazine

7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ethyl 2,4,5-trifluorobenzoylacetate

Downstream raw materials:

1-cyclopropyl-6-fluoro-7-(piperazin-1-yl)quinolin-4(1H)-one

Refernces

Synthesis and antimicrobial activity of a new series of 1,4-dihydropyridine derivatives

10.2298/JSC091127003K

The research focuses on the synthesis and antimicrobial activity of a new series of 1,4-dihydropyridine derivatives. The purpose of the study was to prepare a series of 1,4-dihydropyridine derivatives (1a–g) using Hantzsch syntheses and then react these compounds with thiosemicarbazide to yield a new series of compounds (2a–g). The synthesized compounds were confirmed through IR, 1H-NMR, 13C-NMR, mass spectral, and elemental analysis. The research aimed to evaluate the antimicrobial activity of these compounds, with a particular interest in their potential as vasodilators, antihypertensive, anti-inflammatory, and calcium channel modulators. The conclusions drawn from the study indicated that compound 2c exhibited higher activity than ciprofloxacin against Staphylococcus aureus, and compound 2d showed greater activity than clotrimazole against Candida albicans, suggesting potential for further investigation in the field of antimicrobial agents.

Coumarin-based inhibitors of bacillus anthracis and staphylococcus aureus replicative DNA helicase: Chemical optimization, biological evaluation, and antibacterial activities

10.1021/jm300922h

The study investigates the development of coumarin-based inhibitors targeting the replicative DNA helicase enzymes of Bacillus anthracis and Staphylococcus aureus, aiming to address the growing issue of drug-resistant bacterial infections. The researchers synthesized and evaluated a series of optimized coumarin-based inhibitors, finding that compounds 20 and 22 exhibited the highest potency against the helicases of both bacteria, with IC50 values of 3 and 1 μM, respectively. These compounds also demonstrated potent antibacterial activity against multiple ciprofloxacin-resistant MRSA strains, with MIC values ranging between 0.5 and 4.2 μg/mL. The study highlights the importance of the carboxylic acid group attached to the 3-position of the coumarin core and the substituents at the 7-position in determining the potency of the inhibitors. The findings suggest that further optimization of these coumarin-based helicase inhibitors could lead to the development of a new class of antibacterial agents effective against drug-resistant pathogens.

Antimycobacterial activity of novel 1,2,4-oxadiazole-pyranopyridine/ chromene hybrids generated by chemoselective 1,3-dipolar cycloadditions of nitrile oxides

10.1016/j.bmc.2011.04.033

This study investigates the synthesis and antimycobacterial activity of novel hybrid compounds against Mycobacterium tuberculosis (MTB). The study employs a chemoselective 1,3-dipolar cycloaddition reaction to generate 1,2,4-oxadiazole-pyranopyridine and 1,2,4-oxadiazole-chromene hybrids from 2-aminopyranopyridine-3-carbonitriles and 2-aminochromene-3-carbonitriles, respectively. The synthesized compounds were evaluated for their in vitro antimycobacterial activity against MTB H37Rv strain. The results revealed that the 1,2,4-oxadiazole-pyranopyridine hybrids exhibited enhanced activity compared to the 1,2,4-oxadiazole-chromene hybrids. Notably, compound 5h demonstrated superior potency, being 1.2, 15.2, and 24.6 times more active than the standard drugs isoniazid, ciprofloxacin, and ethambutol, respectively.