Product Name

  • Name

    Enoxacin

  • EINECS 1308068-626-2
  • CAS No. 74011-58-8
  • Article Data5
  • CAS DataBase
  • Density 1.388 g/cm3
  • Solubility 50 mg/ml in 1 M NaOHSlightly soluble in sodium hydroxide, dimethyl sulfoxide, chloroform and methanol. Insoluble in water.
  • Melting Point 220-224 °C
  • Formula C15H17FN4O3
  • Boiling Point 569.9 °C at 760 mmHg
  • Molecular Weight 320.323
  • Flash Point 298.4 °C
  • Transport Information
  • Appearance off-white to yellow crystals
  • Safety 26-36/37
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 74011-58-8 (Enoxacin)
  • Hazard Symbols IrritantXi
  • Synonyms 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylicacid;AT 2266;CI 919;ENOXOR;Enofloxacin;Enofloxacine;Enoksetin;Enoxacine;Flumark;1,8-Naphthyridine-3-carboxylicacid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-;Penetrex;Penetrex (pharmaceutical);
  • PSA 87.46000
  • LogP 1.05710

Synthetic route

7-(4-ethoxycarbonyl-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
92741-52-1

7-(4-ethoxycarbonyl-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

enoxacine
74011-58-8

enoxacine

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 4h; Heating;87%
piperazine
110-85-0

piperazine

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(p-tolylsulfonyl)-1,8-naphthyridine-3-carboxylic acid
114171-68-5

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(p-tolylsulfonyl)-1,8-naphthyridine-3-carboxylic acid

enoxacine
74011-58-8

enoxacine

Conditions
ConditionsYield
With triethylamine In acetonitrile for 0.5h; Heating;68%
ethyl 3-(ethylamino)propanoate
23651-62-9

ethyl 3-(ethylamino)propanoate

enoxacine
74011-58-8

enoxacine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 96 percent / NaHCO3 / dimethylformamide / 8 h / 110 - 120 °C
2: 85 percent / NaH, ethanol / toluene / 2 h / Ambient temperature
3: 94 percent / chloranil / toluene / 1.5 h / Heating
4: 89 percent / 1N-NaOH / dioxane / 1 h / Heating
5: 92 percent / m-chloroperoxybenzoic acid / CHCl3 / 1 h / Ambient temperature; excess of reagent
6: 68 percent / triethylamine / acetonitrile / 0.5 h / Heating
View Scheme
Multi-step reaction with 7 steps
1: 75 percent / NaHCO3 / dimethylformamide / 8 h / 110 - 120 °C
2: 91 percent / NaH, ethanol / toluene / 2 h / Ambient temperature
3: 90 percent / conc. HCl / ethanol / 1 h / 80 °C
4: 94 percent / chloranil / toluene / 1.5 h / Heating
5: 89 percent / 1N-NaOH / dioxane / 1 h / Heating
6: 92 percent / m-chloroperoxybenzoic acid / CHCl3 / 1 h / Ambient temperature; excess of reagent
7: 68 percent / triethylamine / acetonitrile / 0.5 h / Heating
View Scheme
2,6-dichloro-5-fluoro-pyridine-3-carbonitrile
82671-02-1

2,6-dichloro-5-fluoro-pyridine-3-carbonitrile

enoxacine
74011-58-8

enoxacine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 90 percent / KOH / ethanol / 2 h / Ambient temperature
2: 89 percent / KF / dimethylsulfoxide / 1 h / 130 - 135 °C
3: 75 percent / NaHCO3 / dimethylformamide / 8 h / 110 - 120 °C
4: 91 percent / NaH, ethanol / toluene / 2 h / Ambient temperature
5: 90 percent / conc. HCl / ethanol / 1 h / 80 °C
6: 94 percent / chloranil / toluene / 1.5 h / Heating
7: 89 percent / 1N-NaOH / dioxane / 1 h / Heating
8: 92 percent / m-chloroperoxybenzoic acid / CHCl3 / 1 h / Ambient temperature; excess of reagent
9: 68 percent / triethylamine / acetonitrile / 0.5 h / Heating
View Scheme
Multi-step reaction with 10 steps
1: 90 percent / KOH / ethanol / 2 h / Ambient temperature
2: 89 percent / KF / dimethylsulfoxide / 1 h / 130 - 135 °C
3: 84 percent / conc. H2SO4 / 1 h / 50 - 55 °C
4: 98 percent / BF3-etherate / ice-cooling, then 50-60 deg C 30 min, then reflux 23 h
5: 96 percent / NaHCO3 / dimethylformamide / 8 h / 110 - 120 °C
6: 85 percent / NaH, ethanol / toluene / 2 h / Ambient temperature
7: 94 percent / chloranil / toluene / 1.5 h / Heating
8: 89 percent / 1N-NaOH / dioxane / 1 h / Heating
9: 92 percent / m-chloroperoxybenzoic acid / CHCl3 / 1 h / Ambient temperature; excess of reagent
10: 68 percent / triethylamine / acetonitrile / 0.5 h / Heating
View Scheme

Enoxacin Chemical Properties


IUPAC Name: 1-Ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid
Molecular Formula: C15H17FN4O3
Molecular Weight: 320.32 g/mol
Canonical SMILES: c12c(c(c(C(O)=O)cn1CC)=O)cc(F)c(n2)N1CCNCC1
InChI: InChI=1/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)
Product Categories: Active Pharmaceutical Ingredients; API's
Classification Code: Anti-Infective Agents; Antibacterial; Drug / Therapeutic Agent; Enzyme Inhibitors; Mutation data; Nucleic Acid Synthesis Inhibitors; Reproductive Effect
Index of Refraction: 1.598
Molar Refractivity: 78.79 cm3
Molar Volume: 230.6 cm3
Polarizability: 31.23×10-24 cm3
Surface Tension: 58 dyne/cm
Density: 1.388 g/cm3
Flash Point: 298.4 °C
Enthalpy of Vaporization: 89.93 kJ/mol
Boiling Point: 569.9 °C at 760 mmHg
Melting Point: 220-224 °C
storage temperature: 2-8 °C
Vapour Pressure of Enoxacin (CAS NO.74011-58-8): 7.96E-14 mmHg at 25 °C

Enoxacin Uses

 Enoxacin (CAS NO.74011-58-8) is an oral broad-spectrum fluoroquinolone antibacterial agent used in the treatment of urinary tract infections and gonorrhea. Insomnia is a common adverse effect.

Enoxacin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 1600mg/kg (1600mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 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: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA		 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)

BEHAVIORAL: ATAXIA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 Chemotherapy Vol. 32(Suppl,

Enoxacin Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37: Wear suitable protective clothing and gloves.
WGK Germany: 2
RTECS of Enoxacin (CAS NO.74011-58-8): QN2800000

Enoxacin Specification

  Enoxacin (CAS NO.74011-58-8), its Synonyms are 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid ; Comprecin ; Enoram ; Enoxacine ; Enoxacinum ; 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)- .

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