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O8757

Sigma-Aldrich

Ofloxacin

fluoroquinolone antibiotic

Synonym(s):

Dextrofloxacin

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About This Item

Empirical Formula (Hill Notation):
C18H20FN3O4
CAS Number:
82419-36-1
Molecular Weight:
361.37
MDL number:
MFCD00226105
UNSPSC Code:
51282956
PubChem Substance ID:
24278613
NACRES:
NA.76

biological source

synthetic

assay

≥99% (HPLC)

form

powder

solubility

1 M NaOH: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria

mode of action

DNA synthesis | interferes
enzyme | inhibits

storage temp.

2-8°C

InChI

1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)

InChI key

GSDSWSVVBLHKDQ-UHFFFAOYSA-N

Gene Information

human ... CSNK2A1(1457) , KCNH1(3756)
rat ... Gabra1(29705)

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General description

Chemical structure: fluoroquinolone

Application

Ofloxacin is a synthetic fluoroquinolone with broad-spectrum antibacterial activity. It is a nalidixic acid analog. It is given to patients before undergoing retinal reattachment surgery.

Biochem/physiol Actions

Ofloxacin inhibits bacterial DNA gyrase and topoisomerase IV, which haults DNA replication and cell division. Ofloxacin has been shown to convert LytA from the inactive E-form to the active C-form. It is a chiral molecule that inhibits pneumococcal cell wall-degrading virulence factors.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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O Cekiç et al.
The British journal of ophthalmology, 83(10), 1183-1185 (1999-09-30)
To assess the subretinal fluid (SRF) levels of ofloxacin following topical, oral or combined administration. 31 patients undergoing conventional retinal reattachment surgery were randomly assigned to three groups. Nine patients received topical ofloxacin, 11 patients received oral ofloxacin, and the
Carlos Fernández-Tornero et al.
The Journal of biological chemistry, 280(20), 19948-19957 (2005-03-17)
The search for new drugs against Streptococcus pneumoniae (pneumococcus) is driven by the 1.5 million deaths it causes annually. Choline-binding proteins attach to the pneumococcal cell wall through domains that recognize choline moieties, and their involvement in pneumococcal virulence makes
S Güniz Küçükgüzel et al.
European journal of medicinal chemistry, 42(7), 893-901 (2007-04-10)
Three novel series of 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid derivatives namely 4-substituted-1,2,4-triazoline-3-thiones (4a-g); 2-substituted-1,3,4-thiadiazoles (5a-g) and 2-substituted-1,3,4-oxadiazoles (6a-g) have been synthesized. Twenty-one of the newly synthesized compounds were tested against various bacteria, fungi, yeast species and virus. In addition, we have replaced the
Andrea Von Groll et al.
Antimicrobial agents and chemotherapy, 53(10), 4498-4500 (2009-08-19)
This study evaluated cross-resistance of Mycobacterium tuberculosis strains to ofloxacin, moxifloxacin, and gatifloxacin and investigated the presence of mutations in gyrA and gyrB. Fluoroquinolone susceptibilities were determined for 41 M. tuberculosis strains by the proportion method on 7H11, and MICs
Cécile Denève et al.
Antimicrobial agents and chemotherapy, 53(12), 5155-5162 (2009-10-07)
Recent outbreaks of Clostridium difficile infection have been related to the emergence of the NAP1/027 epidemic strain. This strain demonstrates increased virulence and resistance to the C-8-methoxyfluoroquinolones gatifloxacin and moxifloxacin. These antibiotics have been implicated as major C. difficile infection-inducing
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