CHEBI:100147 - nalidixic acid

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ChEBI Name nalidixic acid
Definition A monocarboxylic acid comprising 1,8-naphthyridin-4-one substituted by carboxylic acid, ethyl and methyl groups at positions 3, 1, and 7, respectively. An orally administered antibacterial, it is used in the treatment of lower urinary-tract infections due to Gram-negative bacteria, including the majority of E. coli, Enterobacter, Klebsiella, and Proteus species.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:7456
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Formula C12H12N2O3
Net Charge 0
Average Mass 232.23530
Monoisotopic Mass 232.08479
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)
SMILES CCn1cc(C(O)=O)c(=O)c2ccc(C)nc12
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via quinolone antibiotic )
(via heterocyclic antibiotic )
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
antibacterial drug
A drug used to treat or prevent bacterial infections.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing nalidixic acid (CHEBI:100147) has role antibacterial drug (CHEBI:36047)
nalidixic acid (CHEBI:100147) has role antimicrobial agent (CHEBI:33281)
nalidixic acid (CHEBI:100147) has role DNA synthesis inhibitor (CHEBI:59517)
nalidixic acid (CHEBI:100147) is a 1,8-naphthyridine derivative (CHEBI:73537)
nalidixic acid (CHEBI:100147) is a monocarboxylic acid (CHEBI:25384)
nalidixic acid (CHEBI:100147) is a quinolone antibiotic (CHEBI:86324)
nalidixic acid (CHEBI:100147) is conjugate acid of nalidixic acid anion (CHEBI:62070)
Incoming nalidixic acid anion (CHEBI:62070) is conjugate base of nalidixic acid (CHEBI:100147)
1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
INNs Sources
acide nalidixique ChemIDplus
acido nalidixico ChemIDplus
acidum nalidixicum ChemIDplus
nalidixic acid ChemIDplus
Synonyms Sources
1,4-dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid ChemIDplus
1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure ChemIDplus
1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid ChemIDplus
1-ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid ChemIDplus
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ChEMBL
3-carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one ChemIDplus
Nalidixic acid KEGG COMPOUND
Manual Xrefs Databases
1875 DrugCentral
1880 VSDB
BE612258 Patent
DB00779 DrugBank
Nalidixic_Acid Wikipedia
US3590036 Patent
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Registry Numbers Types Sources
389-08-2 CAS Registry Number KEGG COMPOUND
389-08-2 CAS Registry Number ChemIDplus
750515 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
19 June 2017