93107-08-5

Basic information

• Product Name: 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid hydrochloride
• Synonyms: CIPROFLOXACIN HYDROCHLORIDE;BAY-o-9867;Cyproxan;1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid monohydrochloride;3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, monohydrochloride;3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, hydrochloride;1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid hydrochloride;3-Quinolinecarboxylicacid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-,hydrochloride (1:1)
• CAS NO: 93107-08-5
• Molecular Formula: C₁₇H₁₈FN₃O₃*ClH
• Molecular Weight: 367.8
• EINECS: 642-985-5
• Product Categories: Pharmaceutical intermediate
• Mol File: 93107-08-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: >300 ºC
• Boiling Point: 581.8 °C at 760 mmHg
• Flash Point: 305.6 °C
• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: insoluble in EtOH; ≥33.87 mg/mL in H2O; ≥9.34 mg/mL in DMSO with ultrasonic
• CAS DataBase Reference: 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid hydrochloride(93107-08-5)
• EPA Substance Registry System: 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid hydrochloride(93107-08-5)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: 24/25
• Hazardous Substances Data: 93107-08-5(Hazardous Substances Data)

Usage

Description

Ciprofloxacin hydrochloride is the hydrochloride of ciprofloxacin, which is a synthetic second-generation quinolone antibacterial drug with broad-spectrum antibacterial activity and good bactericidal effect. It is 2 to 4 times stronger than enoxacin, and has antibacterial effects on Enterobacter, Pseudomonas aeruginosa, Haemophilus influenzae, Neisseria gonorrhoeae, Streptococcus, Legionella, and Staphylococcus aureus.

Mechanism of action

Ciprofloxacin hydrochloride is a new type of quinolone antibacterial drug. Its mechanism of action is that it can combine with bacterial DNA gyrase subunit A, thereby inhibiting the cleavage and linking functions of the enzyme, preventing the replication of bacterial DNA, and showing antibacterial effect.

Uses

Different sources of media describe the Uses of 93107-08-5 differently. You can refer to the following data:
1. Anti-bacterial
2. Ciprofloxacin hydrochloride is a fluoroquinolone antibiotic that is widely used as an antimicrobial and immunomodulatory agent. Its range of activity includes most strains of bacterial pathogens capable of inducing respiratory, urinary tract, gastrointestinal, and abdominal infections. It functions by inhibiting DNA gyrase (a type II topoisomerase) and topoisomerase IV, the enzymes responsible for negative supercoiling of chromosomes and DNA strand separation, thus blocking initiation of bacterial replication. Most recently Ciprofloxacin hydrochloride has been used in the management of postexposure inhalational anthrax and radiation combined injury resulting from nuclear disasters.[Cayman Chemical]

Biological Activity

ciprofloxacin (hydrochloride) is a fluoroquinolone antibiotic that has antimicrobial and immunomodulatory activities [1].ciprofloxacin functions by inhibiting dna gyrase and topoisomerase iv, the enzymes responsible for negative supercoiling of chromosomes and dna strand separation, thus blocking initiation of bacterial replication. topoisomerase iv is the primary target of ciprofloxacin in s. aureus [2].ciprofloxacin (hydrochloride) is a fluoroquinolone antibiotic that acts as an antimicrobial and immunomodulatory agent. in b6d2f1/j mice received radiation combined injury (ci), ciprofloxacin significantly reduced pro-inflammatory cytokine and chemokine concentrations (il-6 and kc), and enhanced il-3 production. cip also inhibited ci-induced apoptosis and autophagy in ileal villi, systemic bacterial infection, and iga production [1]. ciprofloxacin (hydrochloride) had been approved by fda for management of postexposure inhalational anthrax. in animals after exposure to aerosolized b. anthracis, ciprofloxacin significantly improved survival rate. ciprofloxacin inhibited the growth of b. anthracis with mic90 of 0.06 μg/ml. in the usamriid rhesus monkey model of inhalational anthrax, the maximum concentration (cmax) of ciprofloxacin was 1.74 μg/ml and the minimum concentration (cmin) was 0.17 μg/ml [3].

references

[1]. fukumoto r, cary lh, gorbunov nv, et al. ciprofloxacin modulates cytokine/chemokine profile in serum, improves bone marrow repopulation, and limits apoptosis and autophagy in ileum after whole body ionizing irradiation combined with skin-wound trauma. plos one. 2013;8(3):e58389.[2]. drlica k, zhao x. dna gyrase, topoisomerase iv, and the 4-quinolones. microbiol mol biol rev. 1997 sep;61(3):377-92.[3]. meyerhoff a, albrecht r, meyer jm, et al. us food and drug administration approval of ciprofloxacin hydrochloride for management of postexposure inhalational anthrax. clin infect dis. 2004 aug 1;39(3):303-8.

InChI:InChI=1/C17H18FN3O3.ClH/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24;/h7-10,19H,1-6H2,(H,23,24);1H

Upstream product

• 110-85-0 piperazine 
• 86393-33-1 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 
• 67-68-5 dimethyl sulfoxide 
• 101799-76-2 3-Cyclopropylamino-2-(2,4,5-trifluorbenzoyl)acrylsaeure-ethylester 
• 138998-46-6 ethyl 3-(dimethylamino)-2-(2,4,5-trifluorobenzoyl)prop-2-enoate 
• 88419-56-1 2,4,5-trifluorobenzoyl chloride 
• 105404-65-7 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate ethyl ester 
• 86393-32-0 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid HCl monohydrate 
• 110600-97-0 ethyl 1-cyclopropyl-6-fluoro-1,4-dihydro-7-nitro-4-oxoquinoline-3-carboxylate 
• 98349-25-8 ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylate 
• 86483-52-5 2,4-dichloro-alpha(elhoxymethlene)-5-fluoro-beta-oxo-benzene propanoic acid ethyl ester 
• 72396-25-9 N-(Cyclopropylamino)acrylsaeure-methylester 
• 86483-50-3 diethyl 2,4-dichloro-5-fluoro-benzoyl-malonate 
• 104599-90-8 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid methyl ester 

Downstream Products

• 103222-12-4 Desethyleneciprofloxacin 

Relevant articles and documents

Preparation method of quinolone carboxylic acid derivative or phthalazinone carboxylic acid derivative

The invention belongs to the field of pharmaceutical chemicals, relates to a preparation method of a quinolone carboxylic acid derivative or a phthalazinone carboxylic acid derivative, and particularly relates to a preparation method of a 7-substituted-3-quinolone carboxylic acid derivative or a 7-substituted-1,5-phthalazinone carboxylic acid derivative. The preparation method comprises the following steps: (1) in an organic solvent, carrying out coupling reaction on a boron chelate II and organic amine III in the presence of an organosilicon compound to obtain a compound IV; and (2) mixing the compound IV with hydrochloric acid, and then filtering and separating the precipitated compound I. Compared with conventional methods, the preparation method provided by the invention has the advantages that the conditions are milder, the hydrolysis of the substrate quinoline carboxylic acid boric acid ester can be reduced, and meanwhile, the influence of a byproduct HF on the product purity is avoided. The method is high in yield and high in purity; compared with the traditional alkali, the organic silicon is more suitable for industrial preparation of the 7-substituted-3-quinolone carboxylic acid derivative or the 7-substituted-1,5-phthalazinone carboxylic acid derivative.

ANTIBIOTIC RESISTANCE BREAKERS

The invention relates to antibiotic compounds of formula (A1) and pharmaceutically acceptable salts, solvates, tautomers and combinations thereof, wherein X and L are optional linkers and one of RA or R1 comprises Ar1, wherein Ar1 is an antibiotic resistance breaker moiety which comprises an optionally substituted C6-10 aryl, C7-13 aralkyl, C5-10 heteroaryl, C6-13 heteroaralkyl, C5-10 heterocyclyl, C6-13 heterocyclalkyl, C3-10 carbocyclyl, C4-13 carbocyclalkyl, -C(=NR')-NR'R'' or –CH2- CH=CH2 group; wherein after administration of the compound to a bacterial infection this moiety reduces or prevents efflux. The invention also discloses pharmaceutical compositions comprising compounds of formula (A1) and the use of such compounds as medicaments, in particular, to treat bacterial infections, such as drug-resistant bacterial infections.

IMPROVED PROCESS FOR THE PREPARATION OF CIPROFLOXACIN AND ITS ACID ADDITION SALTS

An improved process for the synthesis of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid (Ciprofloxacin) or and its acid addition salts preferablyhydrochloride salt with high yield and high purity, the process comprising of reacting 6-fluoro-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid with piperazine in presence of a catalyst in an organic solvent.