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17850

Sigma-Aldrich

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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About This Item

Formule empirique (notation de Hill):
C17H18FN3O3
Numéro CAS:
85721-33-1
Poids moléculaire :
331.34
Numéro Beilstein :
3568352
Numéro MDL:
MFCD00185755
Code UNSPSC :
41116105
ID de substance PubChem :
329751572
Nomenclature NACRES :
NA.21

Agence

EPA 1694

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

powder or crystals

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Application(s)

environmental

Mode d’action

DNA synthesis | interferes
enzyme | inhibits

Chaîne SMILES 

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)

Clé InChI

MYSWGUAQZAJSOK-UHFFFAOYSA-N

Informations sur le gène

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

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Description générale

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000369395
0000369394
0000369395
WXBF4333V
0000369394

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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)
Dongeun Yong et al.
Antimicrobial agents and chemotherapy, 53(12), 5046-5054 (2009-09-23)
A Swedish patient of Indian origin traveled to New Delhi, India, and acquired a urinary tract infection caused by a carbapenem-resistant Klebsiella pneumoniae strain that typed to the sequence type 14 complex. The isolate, Klebsiella pneumoniae 05-506, was shown to
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