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

C₂₄H₂₂FN₅O₂

1-cyclopropyl-6-fluoro-3-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]-7-piperazino-1,4-dihydro-4-quinolinone

Refernces

• 1、 Armstrong, Cameron,Miyai, Yuma,Formosa, Anna,Thomas, Dale,Chen, Esther,Hart, Travis,Schultz, Victor,Desai, Bimbisar K.,Cai, Angela Y.,Almasy, Alexandra,Jensen, Klavs,Rogers, Luke,Roper, Tom. "On-Demand Continuous Manufacturing of Ciprofloxacin in Portable Plug-and-Play Factories: Development of a Highly Efficient Synthesis for Ciprofloxacin". . p. 1524 - 1533. Retrieved 2021/07/21.
• 2、 Mohammed, Aya A. M.,Okechukwu, Patrick N.,Shehadeh, Mayadah B.,Suaifan, Ghadeer A. R. Y.. "Design, synthesis and antimicrobial evaluation of novel glycosylated-fluoroquinolones derivatives". . . Retrieved 2020/07/04.