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Merck
CN

N8878

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

Key Documents

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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
0000511238
0000511238
0000510711
0000510711
BCCN6908

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Suzanne Bialek et al.
Antimicrobial agents and chemotherapy, 54(10), 4373-4378 (2010-08-04)
Cross-resistance to cefoxitin (FOX), chloramphenicol (CMP), and quinolones (nalidixic acid [NAL]) related to a putative efflux system overexpression has recently been reported for Klebsiella pneumoniae. The potential impact of this multidrug resistance (MDR) on the virulence of K. pneumoniae was
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
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
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
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
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