Nalidixic Acid

For research use only. Not for therapeutic Use.

  • CAT Number: A000918
  • CAS Number: 389-08-2
  • Molecular Formula: C12H12N2O3
  • Molecular Weight: 232.24
  • Purity: ≥95%
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Nalidixic Acid(Cat No.:A000918)is a synthetic antibiotic and the first of the quinolone class, effective primarily against gram-negative bacteria. It inhibits bacterial DNA gyrase, an enzyme critical for DNA replication, thus preventing bacterial growth. Commonly used in urinary tract infections, Nalidixic Acid is significant in research for studying DNA synthesis, bacterial resistance mechanisms, and the development of newer fluoroquinolones. Its historical importance and selective activity provide a foundation for investigating bacterial DNA targets, contributing to advancements in antimicrobial therapy and the understanding of quinolone resistance pathways.


Catalog Number A000918
CAS Number 389-08-2
Synonyms

389-08-2; Nalidixin; Nevigramon; Uronidix; Nalidixate

Molecular Formula C12H12N2O3
Purity ≥95%
Target Cell Cycle/DNA Damage
Storage -20°C
IUPAC Name 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
InChI 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)
InChIKey MHWLWQUZZRMNGJ-UHFFFAOYSA-N
SMILES CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O
Reference

1: Xu J, Marsac R, Wei C, Wu F, Boily JF, Hanna K. Cobinding of Pharmaceutical
Compounds at Mineral Surfaces: Mechanistic Modeling of Binding and Cobinding of
Nalidixic Acid and Niflumic Acid at Goethite Surfaces. Environ Sci Technol. 2017
Oct 17;51(20):11617-11624. doi: 10.1021/acs.est.7b02900. Epub 2017 Sep 29. PubMed
PMID: 28902498.

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2: Ahmed M, Kelley SO. Enhancing the Potency of Nalidixic Acid toward a Bacterial
DNA Gyrase with Conjugated Peptides. ACS Chem Biol. 2017 Oct 20;12(10):2563-2569.
doi: 10.1021/acschembio.7b00540. Epub 2017 Sep 1. PubMed PMID: 28825963.

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3: Burckhardt BC, Henjakovic M, Hagos Y, Burckhardt G. Differential Interaction
of Dantrolene, Glafenine, Nalidixic Acid, and Prazosin with Human Organic Anion
Transporters 1 and 3. J Pharmacol Exp Ther. 2017 Sep;362(3):450-458. doi:
10.1124/jpet.117.241406. Epub 2017 Jun 19. PubMed PMID: 28630284.
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4: Loganathan R, Ganeshpandian M, Bhuvanesh NSP, Palaniandavar M, Muruganantham
A, Ghosh SK, Riyasdeen A, Akbarsha MA. DNA and protein binding, double-strand DNA
cleavage and cytotoxicity of mixed ligand copper(II) complexes of the
antibacterial drug nalidixic acid. J Inorg Biochem. 2017 Sep;174:1-13. doi:
10.1016/j.jinorgbio.2017.05.001. Epub 2017 May 3. PubMed PMID: 28551479.
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5: Miladi H, Zmantar T, Kouidhi B, Chaabouni Y, Mahdouani K, Bakhrouf A, Chaieb
K. Use of carvacrol, thymol, and eugenol for biofilm eradication and resistance
modifying susceptibility of Salmonella enterica serovar Typhimurium strains to
nalidixic acid. Microb Pathog. 2017 Mar;104:56-63. doi:
10.1016/j.micpath.2017.01.012. Epub 2017 Jan 3. PubMed PMID: 28062292.
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6: Pati&#241;o Y, Pilehvar S, Díaz E, Ordó&#241;ez S, De Wael K. Electrochemical reduction
of nalidixic acid at glassy carbon electrode modified with multi-walled carbon
nanotubes. J Hazard Mater. 2017 Feb 5;323(Pt B):621-631. doi:
10.1016/j.jhazmat.2016.10.023. Epub 2016 Oct 13. PubMed PMID: 27776850.
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7: Campioni F, Souza RA, Martins VV, Stehling EG, Bergamini AMM, Falc&#227;o JP.
Prevalence of gyrA Mutations in Nalidixic Acid-Resistant Strains of Salmonella
Enteritidis Isolated from Humans, Food, Chickens, and the Farm Environment in
Brazil. Microb Drug Resist. 2017 Jun;23(4):421-428. doi: 10.1089/mdr.2016.0024.
Epub 2016 Aug 25. PubMed PMID: 27559761.
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8: Bergamini FR, Ribeiro MA, Miranda PC, Formiga AL, Corbi PP. A novel binuclear
copper complex incorporating a nalidixic acid derivative displaying a
one-dimensional coordination polymeric structure. Acta Crystallogr C Struct Chem.
2016 Jul 1;72(Pt 7):544-8. doi: 10.1107/S2053229616008913. Epub 2016 Jun 14.
PubMed PMID: 27377275.

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9: Cooper A, Koziol AG, Carrillo CD, Lambert D. Draft Genome Sequences of
Salmonella enterica subsp. enterica Serovar Berta ATCC 8392 and a Nalidixic
Acid-Resistant Isolate of This Strain. Genome Announc. 2016 Apr 21;4(2). pii:
e00186-16. doi: 10.1128/genomeA.00186-16. PubMed PMID: 27103707; PubMed Central
PMCID: PMC4841122.

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10: Naglah AM, Ahmed AF, Wen ZH, Al-Omar MA, Amr Ael-G, Kalmouch A. New Inducible
Nitric Oxide Synthase and Cyclooxygenase-2 Inhibitors, Nalidixic Acid Linked to
Isatin Schiff Bases via Certain l-Amino Acid Bridges. Molecules. 2016 Apr
15;21(4):498. doi: 10.3390/molecules21040498. PubMed PMID: 27092477.

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