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Substance Name: Enoxacin [USAN:INN:BAN:JAN]
RN: 74011-58-8
UNII: 325OGW249P
InChIKey: IDYZIJYBMGIQMJ-UHFFFAOYSA-N

Note

  • A broad-spectrum 6-fluoronaphthyridinone antibacterial agent that is structurally related to NALIDIXIC ACID.

Molecular Formula

  • C15-H17-F-N4-O3

Molecular Weight

  • 320.3223
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Antineoplastic Agents
  • Cytochrome P-450 CYP1A2 Inhibitors
  • Cytochrome P-450 Enzyme Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Nucleic Acid Synthesis Inhibitors
  • Reproductive Effect
  • Topoisomerase II Inhibitors
  • Topoisomerase Inhibitors

Names and Synonyms

Name of Substance

  • Enoxacin
  • Enoxacin [USAN:INN:BAN:JAN]

MeSH Heading

  • Enoxacin

Synonyms

  • 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid
  • AT-2266
  • Bactidan
  • BRN 3628995
  • CCRIS 5242
  • CI 919
  • CI-919
  • Comprecin
  • Enoram
  • Enoxacin
  • Enoxacine
  • Enoxacine [French]
  • Enoxacino
  • Enoxacino [Spanish]
  • Enoxacinum
  • Enoxacinum [Latin]
  • Flumark
  • NSC 627409
  • NSC 629661
  • PD 107779
  • Penetrex
  • UNII-325OGW249P

Systematic Names

  • 1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-
  • 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-
  • Enoxacin

Registry Numbers

CAS Registry Number

  • 74011-58-8

FDA UNII

  • 325OGW249P

System Generated Number

  • 0074011588

Structure Descriptors

InChI

1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)

InChIKey

IDYZIJYBMGIQMJ-UHFFFAOYSA-N

Smiles

c12c(c(c(C(O)=O)cn1CC)=O)cc(F)c(n2)N1CCNCC1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 1600mg/kg (1600mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Chemotherapy Vol. 32(Suppl,
monkey LD50 oral > 1600mg/kg (1600mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Chemotherapy Vol. 32(Suppl,
mouse LD50 intraperitoneal 3600mg/kg (3600mg/kg)   Ensho. Japanese Journal of Inflammation. Vol. 11, Pg. 343, 1991.
mouse LD50 intravenous 327mg/kg (327mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Chemotherapy Vol. 32(Suppl,
mouse LD50 oral > 4gm/kg (4000mg/kg)   European Patent Application. Vol. #0009425,
mouse LD50 subcutaneous 1100mg/kg (1100mg/kg)   "Current Chemotherapy and Infectious Diseases, Proceedings of the 11th International Congress of Chemotherapy and the 19th Interscience Conference on Antimicrobial Agents and Chemotherapy, Boston, MA, 1979," Washington, DC, American Soc. for Microbiology, 1980Vol. 1, Pg. 456, 1980.
rat LD50 intravenous 236mg/kg (236mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Chemotherapy Vol. 32(Suppl,
rat LD50 oral > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 32(Suppl,
rat LD50 subcutaneous > 2gm/kg (2000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: ATAXIA
Chemotherapy Vol. 32(Suppl,

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 220-224 deg C   EXP
log P (octanol-water) -0.2 (none)   EXP
Water Solubility 3.43E+04 mg/L 25 EST
Vapor Pressure 4.79E-13 mm Hg 25 EST
Henry's Law Constant 1.14E-21 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.22E-10 cm3/molecule-sec 25 EST

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