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Substance Name: Norfloxacin [USAN:USP:INN:BAN:JAN]
RN: 70458-96-7
UNII: N0F8P22L1P
InChIKey: OGJPXUAPXNRGGI-UHFFFAOYSA-N

Note

  • A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.

Molecular Formula

  • C16-H18-F-N3-O3

Molecular Weight

  • 319.3342
 

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
  • Human Data
  • Metabolic Side Effects of Drugs and Substances
  • Mutation Data
  • Nucleic Acid Synthesis Inhibitors
  • Reproductive Effect
  • Topoisomerase II Inhibitors
  • Topoisomerase Inhibitors

Names and Synonyms

Name of Substance

  • Norfloxacin
  • Norfloxacin [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Norfloxacin

Synonyms

  • 1,4-Dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
  • 1-Ethyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-chinolincarbonsaeure
  • 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
  • 5-23-03-00135 (Beilstein Handbook Reference)
  • AM 715
  • AM-715
  • Baccidal
  • Barazan
  • BRN 0567897
  • CCRIS 6302
  • Chibroxin
  • EINECS 274-614-4
  • Fulgram
  • HSDB 8029
  • MK 0366
  • MK-366
  • Norfloxacin
  • Norfloxacine
  • Norfloxacine [INN-French]
  • Norfloxacino
  • Norfloxacino [INN-Spanish]
  • Norfloxacinum
  • Norfloxacinum [INN-Latin]
  • Noroxin
  • Sebercim
  • UNII-N0F8P22L1P

Systematic Names

  • 3-Quinolinecarboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-
  • 3-Quinolinecarboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-
  • Norfloxacin

Registry Numbers

CAS Registry Number

  • 70458-96-7

FDA UNII

  • N0F8P22L1P

System Generated Number

  • 0070458967

Structure Descriptors

InChI

1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)

InChIKey

OGJPXUAPXNRGGI-UHFFFAOYSA-N

Smiles

c12c(c(=O)c(cn1CC)C(=O)O)cc(c(c2)N1CCNCC1)F

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 oral > 4gm/kg (4000mg/kg)   Journal of Medicinal Chemistry. Vol. 32, Pg. 671, 1989.
man TDLo oral 94mg/kg/13D-I (94mg/kg) MUSCULOSKELETAL: OTHER CHANGES New Zealand Medical Journal. Vol. 96, Pg. 590, 1983.
mouse LD50 intramuscular 470mg/kg (470mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Chemotherapy Vol. 29(Suppl,
mouse LD50 intraperitoneal 1064mg/kg (1064mg/kg)   Ensho. Japanese Journal of Inflammation. Vol. 11, Pg. 343, 1991.
mouse LD50 intravenous 220mg/kg (220mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chemotherapy Vol. 29(Suppl,
mouse LD50 oral 4gm/kg (4000mg/kg)   Journal of Medicinal Chemistry. Vol. 30, Pg. 2163, 1987.
mouse LD50 subcutaneous > 1500mg/kg (1500mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 1625, 1984.
rat LD50 intramuscular > 500mg/kg (500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemotherapy Vol. 29(Suppl,
rat LD50 intravenous 245mg/kg (245mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chemotherapy Vol. 29(Suppl,
rat LD50 oral > 4gm/kg (4000mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 1625, 1984.
rat LD50 subcutaneous > 1500mg/kg (1500mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 1625, 1984.
women TDLo oral 48mg/kg/2D-I (48mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

BEHAVIORAL: MUSCLE WEAKNESS
Medical Journal of Australia. Vol. 159, Pg. 423, 1993.
women TDLo oral 48mg/kg/2D-I (48mg/kg) MUSCULOSKELETAL: JOINTS

BEHAVIORAL: MUSCLE WEAKNESS

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"
Medical Journal of Australia. Vol. 159, Pg. 423, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 227-228 deg C   EXP
log P (octanol-water) -1.03E+00 (none)   EXP
Water Solubility 1.78E+05 mg/L 25 EST
Vapor Pressure 6.77E-13 mm Hg 25 EST
Henry's Law Constant 8.70E-19 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.22E-10 cm3/molecule-sec 25 EST

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