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17850

Sigma-Aldrich

Ciprofloxacin

≥98% (HPLC)

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Synonym(s):
1-Cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid, Ciprobay
Empirical Formula (Hill Notation):
C17H18FN3O3
CAS Number:
Molecular Weight:
331.34
Beilstein/REAXYS Number:
3568352
MDL number:
PubChem Substance ID:

agency

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

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This Item
PHR1167Y00001981134313
vibrant-m

17850

Ciprofloxacin

vibrant-m

PHR1167

Ciprofloxacin

vibrant-m

Y0000198

Ciprofloxacin

vibrant-m

1134313

Ciprofloxacin

mode of action

DNA synthesis | interferes, enzyme | inhibits

mode of action

-

mode of action

-

mode of action

-

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

-

antibiotic activity spectrum

-

antibiotic activity spectrum

-

application(s)

environmental

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

Gene Information

human ... CYP1A2(1544), KCNH1(3756)
rat ... Gabra1(29705)

Gene Information

-

Gene Information

-

Gene Information

-

assay

≥98% (HPLC)

assay

-

assay

-

assay

-

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

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
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)
Gisele Peirano et al.
Antimicrobial agents and chemotherapy, 54(3), 1327-1330 (2010-01-06)
Phenotypic and genotypic methods were used to characterize extended-spectrum-beta-lactamase (ESBL)-producing Escherichia coli isolated in 2007 from 11 different Canadian medical centers. Of the 209 ESBL-producing E. coli isolates tested, 148 (71%) produced CTX-M-15, 17 (8%) produced CTX-M-14, 5 (2%) produced

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