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N8878

Sigma-Aldrich

Nalidixic acid

≥98%

Synonym(s):

1,4-Dihydro-1-ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid, 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C12H12N2O3
CAS Number:
389-08-2
Molecular Weight:
232.24
Beilstein:
750515
EC Number:
206-864-7
MDL number:
MFCD00006884
UNSPSC Code:
12352106
PubChem Substance ID:
24897864
NACRES:
NA.77

biological source

synthetic

Quality Level

200

Assay

≥98%

form

powder

mp

227-229 °C (lit.)

solubility

chloroform: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

DNA synthesis | interferes
enzyme | inhibits

SMILES string

CCN1C=C(C(O)=O)C(=O)c2ccc(C)nc12

InChI

1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

InChI key

MHWLWQUZZRMNGJ-UHFFFAOYSA-N

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General description

Chemical structure: quinolone

Application

Used to modulate (inhibit) bacterial DNA gyrase-dependent processes such as DNA polymerization, (ATP-dependen)t DNA supercoiling, and chromosome fragmentation.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000400938
0000400867
BCCM4347
0000355266
0000400938

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Valeria Bortolaia et al.
Antimicrobial agents and chemotherapy, 54(4), 1623-1626 (2010-01-27)
We characterized 67 Escherichia coli isolates with reduced susceptibility to cefotaxime or ceftiofur obtained from healthy broilers housed in five Italian farms. The bla(CTX-M-1), bla(CTX-M-32) and bla(SHV-12) beta-lactamase genes were identified on IncI1, IncN, or IncFIB plasmids. Considerable genetic diversity
Lucia Pallecchi et al.
Antimicrobial agents and chemotherapy, 51(8), 2720-2725 (2007-06-06)
A survey carried out in 2005 among members of a healthy population of children living in Bolivia and Peru revealed that fecal carriage of Escherichia coli strains resistant to expanded-spectrum cephalosporins was remarkably increased compared to that observed in the
Inna Chmelnitsky et al.
Antimicrobial agents and chemotherapy, 52(8), 2962-2965 (2008-06-04)
Fourteen out of 16 carbapenem-resistant quinolone-susceptible Enterobacter cloacae isolates were found to carry qnrB2 and bla(KPC-2) genes encoded on the same plasmid. One isolate also carried the aac(6')-Ib-cr gene. Coexistence of quinolone resistance determinants and bla(KPC-2) on the same plasmid
Kate S Baker et al.
The Lancet. Infectious diseases, 15(8), 913-921 (2015-05-06)
Shigellosis is an acute, severe bacterial colitis that, in high-income countries, is typically associated with travel to high-risk regions (Africa, Asia, and Latin America). Since the 1970s, shigellosis has also been reported as a sexually transmitted infection in men who
Michelle D Brazas et al.
Antimicrobial agents and chemotherapy, 51(12), 4276-4283 (2007-09-26)
With few novel antimicrobials in the pharmaceutical pipeline, resistance to the current selection of antibiotics represents a significant therapeutic challenge. Microbial persistence in subinhibitory antibiotic environments has been proposed to contribute to the development of resistance. Pseudomonas aeruginosa cultures pretreated
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