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70162

Sigma-Aldrich

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:
389-08-2
Molecular Weight:
232.24
Beilstein:
750515
EC Number:
206-864-7
MDL number:
MFCD00006884
UNSPSC Code:
12352200
Pricing and availability is not currently available.

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

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

Other Notes

Inhibitor of bacterial DNA synthesis[1]

replaced by

Product No.
Description
Pricing

N8878

Nalidixic acid, ≥98%

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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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)
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
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
F Petronella et al.
Chemosphere, 91(7), 941-947 (2013-03-08)
Two different nanosized TiO2-based catalysts supported onto glass with tailored photocatalytic properties upon irradiation by UV light were successfully employed for the degradation of nalidixid acid, a widely diffused antibacterial agent of environmental relevance known to be non-biodegradable. Anatase rod-like
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
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