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Substance Name: Oxolinic acid [USAN:INN:BAN]
RN: 14698-29-4
UNII: L0A22B22FT
InChIKey: KYGZCKSPAKDVKC-UHFFFAOYSA-N

Note

  • Synthetic antimicrobial related to NALIDIXIC ACID and used in URINARY TRACT INFECTIONS.

Molecular Formula

  • C13-H11-N-O5

Molecular Weight

  • 261.2319
 

Classification Codes

  • Agricultural Chemical
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Anti-Infective Agents, Urinary
  • Antibacterial
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Fungicide, Bactericide, Wood Preservative
  • Mutation Data
  • Nucleic Acid Synthesis Inhibitors
  • Renal Agents
  • Topoisomerase II Inhibitors
  • Topoisomerase Inhibitors
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Oxolinic acid
  • Oxolinic acid [USAN:INN:BAN]

MeSH Heading

  • Oxolinic acid

Synonyms

  • 1,3-Dioxolo(4,5-g)quinoline-7-carboxylic acid, 5-ethyl-5,8-dihydro-8-oxo-
  • 1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid
  • 1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic acid
  • 5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid
  • Acide oxolinique
  • Acide oxolinique [INN-French]
  • Acido ossolico
  • Acido ossolico [DCIT]
  • Acido oxolinico
  • Acido oxolinico [INN-Spanish]
  • Acidum oxolinicum
  • Acidum oxolinicum [INN-Latin]
  • BRN 0620635
  • CCRIS 6301
  • Cistopax
  • Dioxacin
  • EINECS 238-750-8
  • Emyrenil
  • Gramurin
  • HSDB 3243
  • Nidantin
  • NSC 110364
  • NSC-110364
  • Oksaren
  • Orthurine
  • Ossian
  • Oxoboi
  • Oxolinic
  • Oxolinic acid
  • Pietil
  • Prodoxal
  • Prodoxol
  • S-0208
  • Starner
  • Tiurasin
  • Ultibid
  • UNII-L0A22B22FT
  • Uritrate
  • Uro-alvar
  • Urotrate
  • Uroxol
  • Utibid
  • W 4565

Systematic Names

  • 1,3-Dioxolo(4,5-g)quinoline-7-carboxylic acid, 5-ethyl-5,8-dihydro-8-oxo-
  • Oxolinic acid

Registry Numbers

CAS Registry Number

  • 14698-29-4

FDA UNII

  • L0A22B22FT

System Generated Number

  • 0014698294

Structure Descriptors

InChI

1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)

InChIKey

KYGZCKSPAKDVKC-UHFFFAOYSA-N

Smiles

c12c(cc3c(c2)OCO3)c(=O)c(cn1CC)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 1gm/kg (1000mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 475, 1967.
hamster LD50 oral > 6gm/kg (6000mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 475, 1967.
mouse LD50 intravenous 177mg/kg (177mg/kg)   United States Patent Document. Vol. #4292317,
mouse LD50 oral 1890mg/kg (1890mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 oral 525mg/kg (525mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 skin > 2gm/kg (2000mg/kg)   Japan Pesticide Information. Vol. (55), Pg. 21, 1989.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 315 dec deg C   EXP
pKa Dissociation Constant 6.87 (none) 26 EXP
log P (octanol-water) 0.94 (none)   EXP
Water Solubility 3.2 mg/L 25 EXP
Vapor Pressure 4.75E-08 mm Hg 25 EST
Henry's Law Constant 4.12E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.26E-10 cm3/molecule-sec 25 EST

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