CAS No.74011-58-8,Enoxacin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	74011-58-8
Name:	Enoxacin
Article Data:	5

Formula:	C₁₅H₁₇FN₄O₃
Molecular Weight:	320.323
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);
EINECS:	1308068-626-2
Density:	1.388 g/cm³
Melting Point:	220-224 °C
Boiling Point:	569.9 °C at 760 mmHg
Flash Point:	298.4 °C
Solubility:	50 mg/ml in 1 M NaOHSlightly soluble in sodium hydroxide, dimethyl sulfoxide, chloroform and methanol. Insoluble in water.
Appearance:	off-white to yellow crystals
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36/37
PSA:	87.46000
LogP:	1.05710

Synthetic route

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

: 74011-58-8
enoxacine

Conditions

Conditions	Yield
With sodium hydroxide In ethanol for 4h; Heating;	87%

: 110-85-0
piperazine

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

: 74011-58-8
enoxacine

Conditions

Conditions	Yield
With triethylamine In acetonitrile for 0.5h; Heating;	68%

: 23651-62-9
ethyl 3-(ethylamino)propanoate

: 74011-58-8
enoxacine

Conditions

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

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

: 82671-02-1
2,6-dichloro-5-fluoro-pyridine-3-carbonitrile

: 74011-58-8
enoxacine

Conditions

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

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

Total:120 Page 1 of 4 1 2 3 4 Next>>

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Chemistry

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

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.

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,

Safety Profile

Hazard Codes: Irritant 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

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)- .