17850
Ciprofloxacin
≥98% (HPLC)
Synonyme(s) :
1-Cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid, Ciprobay
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A propos de cet article
Formule empirique (notation de Hill) :
C17H18FN3O3
Numéro CAS:
Poids moléculaire :
331.34
UNSPSC Code:
41116105
NACRES:
NA.21
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3568352
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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.
Classe de stockage
11 - Combustible Solids
wgk
WGK 2
ppe
Eyeshields, Gloves, type N95 (US)
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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)
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
Athina Andrea et al.
Microorganisms, 7(3) (2019-03-22)
Among non-mammalian infection model organisms, the larvae of the greater wax moth Galleria mellonella have seen increasing popularity in recent years. Unlike other invertebrate models, these larvae can be incubated at 37 °C and can be dosed relatively precisely. Despite