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Substance Name: Nalidixic acid [USAN:USP:INN:BAN:JAN]
RN: 389-08-2
UNII: 3B91HWA56M
InChIKey: MHWLWQUZZRMNGJ-UHFFFAOYSA-N

Note

  • A synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA GYRASE.

Molecular Formula

  • C12-H12-N2-O3

Molecular Weight

  • 232.238
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Nucleic Acid Synthesis Inhibitors
  • Reproductive Effect
  • Topoisomerase II Inhibitors
  • Topoisomerase Inhibitors
  • Tumor Data

Names and Synonyms

Name of Substance

  • Nalidixic acid
  • Nalidixic acid [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Nalidixic acid

Synonyms

  • 1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
  • 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure
  • 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure [German]
  • 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
  • 1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid
  • 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
  • 3-Carboxy-1-ethyl-7-methyl-1,8-naphthidin-4-one
  • 3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one
  • 5-25-07-00384 (Beilstein Handbook Reference)
  • Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico
  • Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico [Italian]
  • Acide nalidixico
  • Acide nalidixico [Italian]
  • Acide nalidixique
  • Acide nalidixique [French]
  • Acide nalidixique [INN-French]
  • Acido nalidissico
  • Acido nalidissico [DCIT]
  • Acido nalidixico
  • Acido nalidixico [INN-Spanish]
  • Acidum nalidixicum
  • Acidum nalidixicum [INN-Latin]
  • Betaxina
  • BRN 0750515
  • CCRIS 2365
  • Cybis
  • Dixiben
  • Dixinal
  • EINECS 206-864-7
  • HSDB 3241
  • Innoxalon
  • Jicsron
  • Kusnarin
  • Naldixic acid
  • Nalidic acid
  • Nalidicron
  • Nalidixan
  • Nalidixate
  • Nalidixic acid
  • Nalidixin
  • Nalidixinic acid
  • Nalitucsan
  • Nalix
  • Nalurin
  • Narigix
  • Naxuril
  • NCI-C56199
  • NegGram
  • Nevigramon
  • Nicelate
  • Nogram
  • NSC-82174
  • Poleon
  • Sicmylon
  • Specifen
  • Specifin
  • Unaserus
  • UNII-3B91HWA56M
  • Uralgin
  • Uriben
  • Uriclar
  • Urisal
  • Urodixin
  • Uroman
  • Uroneg
  • Uronidix
  • Uropan
  • WIN 18,320
  • Wintomylon

Systematic Names

  • 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-
  • Nalidixic acid

Superlist Name

  • Nalidixic acid

Registry Numbers

CAS Registry Number

  • 389-08-2

FDA UNII

  • 3B91HWA56M

Related Registry Number

  • 3374-05-8 (hydrochloride salt, anhydrous)

System Generated Number

  • 0000389082

Structure Descriptors

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

c12c(c(c(C(O)=O)cn1CC)=O)ccc(n2)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo unreported 1200mg/kg/20D (1200mg/kg) BLOOD: OTHER CHANGES "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 414, 1969.
mouse LD50 intraperitoneal 600mg/kg (600mg/kg)   United States Patent Document. Vol. #4552882,
mouse LD50 intravenous 101mg/kg (101mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 117, 1970.
mouse LD50 oral 572mg/kg (572mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
mouse LD50 subcutaneous 500mg/kg (500mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 intraperitoneal 319mg/kg (319mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 117, 1970.
rat LD50 intravenous 1160mg/kg (1160mg/kg)   Drugs in Japan Vol. -, Pg. 908, 1995.
rat LD50 oral 2040mg/kg (2040mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Chemotherapy Vol. 28(Suppl,
rat LD50 subcutaneous 1584mg/kg (1584mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 117, 1970.
women TDLo oral 40mg/kg (40mg/kg) BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE

BEHAVIORAL: COMA
Acta Medica Scandinavica. Vol. 216, Pg. 237, 1984.
women TDLo oral 160mg/kg/2D (160mg/kg) SKIN AND APPENDAGES (SKIN): SWEATING: OTHER

ENDOCRINE: HYPERGLYCEMIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
British Medical Journal. Vol. 2, Pg. 1518, 1977.
women TDLo oral 560mg/kg (560mg/kg) BEHAVIORAL: COMA

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Intensive Care Medicine. Vol. 5, Pg. 141, 1979.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 229.5 deg C   EXP
pKa Dissociation Constant 8.6 (none)   EXP
log P (octanol-water) 1.59 (none)   EXP
Water Solubility 100 mg/L 23 EXP
Vapor Pressure 3.56E-07 mm Hg 25 EST
Henry's Law Constant 5.12E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.15E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.