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7-(4-ethoxycarbonyl-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
enoxacine
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 4h; Heating; | 87% |
piperazine
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(p-tolylsulfonyl)-1,8-naphthyridine-3-carboxylic acid
enoxacine
Conditions | Yield |
---|---|
With triethylamine In acetonitrile for 0.5h; Heating; | 68% |
ethyl 3-(ethylamino)propanoate
enoxacine
Conditions | Yield |
---|---|
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
enoxacine
Conditions | Yield |
---|---|
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 |
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 (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.
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, |
Hazard Codes: Xi
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 (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)- .