17850
Ciprofloxacin
≥98% (HPLC)
Sinónimos:
1-Cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid, Ciprobay
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Fórmula empírica (notación de Hill):
C17H18FN3O3
Número CAS:
Peso molecular:
331.34
UNSPSC Code:
41116105
NACRES:
NA.21
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3568352
Servicio técnico
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EPA 1694
Quality Level
assay
≥98% (HPLC)
form
powder or crystals
antibiotic activity spectrum
Gram-negative bacteria, Gram-positive bacteria
application(s)
environmental
mode of action
DNA synthesis | interferes, enzyme | inhibits
SMILES string
OC(=O)C1=CN(C2CC2)c3cc(N4CCNCC4)c(F)cc3C1=O
InChI
1S/C17H18FN3O3/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)
InChI key
MYSWGUAQZAJSOK-UHFFFAOYSA-N
Gene Information
human ... CYP1A2(1544), KCNH1(3756)
rat ... Gabra1(29705)
General description
Ciprofloxacin is a second-generation broad-spectrum fluoroquinolone antibiotic with extensive antimicrobial and pharmacokinetic properties that is widely used to combat bacterial infections. Its chemical name is 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid.
Chemical structure: fluoroquinolone
Chemical structure: fluoroquinolone
Application
Ciprofloxacin is widely used in clinical practices against Gram-positive and Gram-negative bacteria and the treatment of a broad range of infections, including those of the skin, eyes, urinary tract, lower respiratory tract, gastrointestinal tract, et cetera. It can also be combined with various antimicrobial agents to combat bacterial biofilms as well as multidrug-resistant microorganisms. Its derivatives have been developed to synthesize novel antibacterials with enhanced potency and diverse antimicrobial effects including antibacterial, antifungal, anti-HIV, anti-tumor, and anti-TB properties.
Biochem/physiol Actions
The mechanism of action of Ciprofloxacin is the inhibition of bacterial DNA synthesis by blocking the subunit A of DNA gyrase enzyme as well as by affecting the bacterial cell wall.
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 2
ppe
Eyeshields, Gloves, type N95 (US)
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Gui-Fu Zhang et al.
European journal of medicinal chemistry, 146, 599-612 (2018-02-07)
Bacterial infections represent a significant health threat globally, and are responsible for the majority of hospital-acquired infections, leading to extensive mortality and burden on global healthcare systems. The second generation fluoroquinolone ciprofloxacin which exhibits excellent antimicrobial activity and pharmacokinetic properties
The resistance mechanisms of bacteria against ciprofloxacin and new approaches for enhancing the efficacy of this antibiotic
Shariati et al.
Frontiers in public health, 10 (2022)
Orjan Samuelsen et al.
Antimicrobial agents and chemotherapy, 54(1), 346-352 (2009-11-04)
Scandinavia is considered a region with a low prevalence of antimicrobial resistance. However, the number of multidrug-resistant (MDR) Gram-negative bacteria is increasing, including metallo-beta-lactamase (MBL)-producing Pseudomonas aeruginosa. In this study MBL-producing P. aeruginosa isolates identified in Norway (n = 4)