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Showing drug card for Nalidixic Acid (DB00779)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:09
Primary Accession Number DB00779
Secondary Accession Number
  • APRD01133
Name Nalidixic Acid
Drug Type
  • Approved
  • Small Molecule
Description A synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA gyrase. [PubChem]
Synonyms Not Available
Brand Names
  1. Cybis
  2. Dixiben
  3. Dixinal
  4. Eucistin
  5. Innoxalon
  6. Jicsron
  7. Nalidic acid
  8. Nalidixan
  9. Nalidixate
  10. Nalidixic acid USP27
  11. Nalidixin
  12. Nalidixinic acid
  13. Nalitucsan
  14. Nalix
  15. Nalurin
  16. Naxuril
  17. NegGram
  18. Negram
  19. Nevigramon
  20. Nogram
  21. Sicmylon
  22. Unaserus
  23. Urisal
  24. Uronidix
  25. Wintomylon
  26. Wintron
  27. naladixic acid
Brand Mixtures Not Available
Chemical IUPAC Name 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
Chemical Formula C12H12N2O3
Chemical Structure Structure
CAS Registry Number 389-08-2
InChI Identifier InChI=1/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)/f/h16H
InChI Key MHWLWQUZZRMNGJ-WYUMXYHSCS
KEGG Drug D00183 Link Image
KEGG Compound C05079 Link Image
PubChem Compound 4421 Link Image
PubChem Substance 7525 Link Image
ChEBI ID Not Available
PharmGKB ID PA450583 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link http://www.rxlist.com/cgi/generic2/nalidixicacid.htm Link Image
PDRhealth Link Not Available
Wikipedia Link Not Available
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 232.2353
Monoisotopic Molecular Weight 232.0848
State Solid
Melting Point 229.5 oC
Experimental Water Solubility 100 mg/L Source: PhysProp
Predicted Water Solubility 2.30e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 2.1 Source: PhysProp
Predicted LogP 0.96 Calculated using ALOGPS
Experimental LogS -3.37 [ADME Research, USCD]
Predicted LogS -2.00 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point 8.6
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2
Canonical SMILES CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2
Drug Category
  • Anti-Infective Agents
  • Enzyme Inhibitors
  • Nucleic Acid Synthesis Inhibitors
ATC Codes
AHFS Codes
  • 08:12.18
Indication For the treatment of urinary tract infections caused by susceptible gram-negative microorganisms, including the majority of E. Coli, Enterobacter species, Klebsiella species, and Proteus species.
Pharmacology Nalidixic acid is a quinolone antibacterial agent for oral administration. Nalidixic acid has marked antibacterial activity against gram-negative bacteria including Enterobacter species, Escherichia coli, Morganella Morganii; Proteus Mirabilis, Proteus vulgaris, and Providencia rettgeri. Pseudomonas species are generally resistant to the drug. Nalidixic acid is bactericidal and is effective over the entire urinary pH range. Conventional chromosomal resistance to nalidixic acid taken in full dosage has been reported to emerge in approximately 2 to 14 percent of patients during treatment; however, bacterial resistance to nalidixic acid has not been shown to be transferable via R factor.
Mechanism of Action Evidence exists that the active metabolite, hydroxynalidixic acid, binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis.
Absorption Following oral administration, nalidixic acid is rapidly absorbed from the gastrointestinal tract. Bioavailability is approximately 96%. Absorption may be delayed if taken with antacids.
Toxicity ORAL (LD50): Acute: 1160 mg/kg [Rat]. 572 mg/kg [Mouse]. Toxic psychosis, convulsions, increased intracranial pressure, or metabolic acidosis may occur in patients taking more than the recommended dosage. Vomiting, nausea, and lethargy may also occur following overdosage.
Protein Binding Nalidixic acid is 93% bound to protein in the blood, and the active metabolite, hydroxynalidixic acid is 63% bound.
Biotransformation Hepatic. 30% of administered dose is metabolized to the active metabolite, hydroxynalidixic acid. Rapid conjugation of parent drug and active metabolite to inactive metabolites. Metabolism may vary widely among individuals. In the urine, hydroxynalidixic acid represents 80 to 85% of the antibacterial activity.
Half Life 1.1 to 2.5 hours in healthy adult patients, and up to 21 hours in patients with impaired renal function.
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol The quinolone increases the anticoagulant effect
Anisindione The quinolone increases the anticoagulant effect
Dicumarol The quinolone increases the anticoagulant effect
Warfarin The quinolone increases the anticoagulant effect
Food Interactions
  • Take with food to reduce irritation. Drink liberally.
Pathways Not Available
General References
  1. RxList Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. DNA
Drug Target 1 [top]
Target 1 ID 874
Target 1 Name DNA
Target 1 Synonyms
  1. Deoxyribonucleic acid
Target 1 Gene Name Not Available
Target 1 Protein Sequence Not Available
Target 1 Number of Residues 0
Target 1 Molecular Weight 7656 (double strand)
Target 1 Theoretical pI Not Available
Target 1 GO Classification
Function
information storage
information transfer
Process
DNA replication and chromosomal cycle
DNA replication
DNA-dependent DNA replication
DNA replication, synthesis of RNA primer
transcription
transcription, DNA dependent
Component
cell
intracellular
nucleus
mitochondria
Target 1 General Function Biological information storage and information transfer
Target 1 Specific Function DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
Target 1 Pathways
Name SMPDB Link KEGG Link
DNA polymerase map03030 Link Image
RNA polymerase map03020 Link Image
Target 1 Reactions
  • DNA + DNA polymerase + nNTP = 2 DNA + nNDP; DNA + RNA polymerase + NTP = mRNA + nNDP
Target 1 Pfam Domain Function Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB/Swiss-Prot ID Not Available
Target 1 UniProtKB/Swiss-Prot Entry Name Not Available
Target 1 PDB ID 1BNA Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Nucleus and mitochondria
Target 1 Gene Sequence >Example: Dickerson dodecamer 
CGCGAATTCGCG
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus All loci
Target 1 SNPs Not Available
Target 1 General References
  1. Nadeau D, Marchand C: Change in the kinetics of sulphacetamide tissue distribution in Walker tumor-bearing rats. Drug Metab Dispos. 1975 Nov-Dec;3(6):565-76. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  3. Avsaroglu MD, Helmuth R, Junker E, Hertwig S, Schroeter A, Akcelik M, Bozoglu F, Guerra B: Plasmid-mediated quinolone resistance conferred by qnrS1 in Salmonella enterica serovar Virchow isolated from Turkish food of avian origin. J Antimicrob Chemother. 2007 Sep 19;. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.