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Merck
CN

70162

Nalidixic acid

≥99.0% (T)

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:
Molecular Weight:
232.24
EC Number:
206-864-7
UNSPSC Code:
12352200
MDL number:
Beilstein/REAXYS Number:
750515
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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

SMILES string

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

assay

≥99.0% (T)

mp

227-229 °C (lit.), 228-230 °C

solubility

chloroform: 20 mg/mL, clear

mode of action

DNA synthesis | interferes, enzyme | inhibits

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General description

Chemical structure: quinolone

Other Notes

Inhibitor of bacterial DNA synthesis

pictograms

Health hazardExclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

Regulatory Information

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Studies on the mode of action of nalidixic acid.
A M Pedrini et al.
European journal of biochemistry, 25(2), 359-365 (1972-02-15)
Christopher M Parry
Transactions of the Royal Society of Tropical Medicine and Hygiene, 98(7), 413-422 (2004-05-13)
Multidrug-resistant (MDR) Salmonella Typhi (resistant to chloramphenicol, ampicillin, and trimethoprim-sulphamethoxazole) and isolates with reduced susceptibility to fluoroquinolones (indicated by resistance to nalidixic acid, NaR) have caused epidemics and become endemic in southern Viet Nam during the 1990s. Short courses of
Migla Miskinyte et al.
Antimicrobial agents and chemotherapy, 57(1), 189-195 (2012-10-24)
Mutations causing antibiotic resistance usually incur a fitness cost in the absence of antibiotics. The magnitude of such costs is known to vary with the environment. Little is known about the fitness effects of antibiotic resistance mutations when bacteria confront
Robert J Commons et al.
The Medical journal of Australia, 196(5), 332-336 (2012-03-22)
To determine incidence and trends in antibiotic resistance in Australian Salmonella enterica subspecies enterica serovars Typhi (S. Typhi) and Paratyphi (S. Paratyphi) isolates over the past 26 years. A retrospective analysis of consecutive microbiologically confirmed enteric fever isolates. All S.
George X Song-Zhao et al.
Mucosal immunology, 7(4), 763-774 (2013-11-28)
Polymorphisms in the intracellular pattern recognition receptor gene NLRP3 (NLR family, pyrin domain containing 3) have been associated with susceptibility to Crohn's disease, a type of inflammatory bowel disease. Following tissue damage or infection, NLRP3 triggers the formation of inflammasomes

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