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Merck
CN

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

Key Documents

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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

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

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)
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
Fumie Adachi et al.
The Science of the total environment, 444, 508-514 (2013-01-08)
Fluoroquinolones (FQs) have been detected in aquatic environments in several countries. Long-term exposure to low levels of antimicrobial agents provides selective pressure, which might alter the sensitivity of bacteria to antimicrobial agents in the environment. Here, we examined FQ levels
Drug therapy reviews: nalidixic acid.
R Gleckman et al.
American journal of hospital pharmacy, 36(8), 1071-1076 (1979-08-01)
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