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Enrofloxacin

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Name

Enrofloxacin

EINECS 618-911-2
CAS No. 93106-60-6 Density 1.385 g/cm3
PSA 65.78000 LogP 2.31850
Solubility Soluble in chloroform. Slightly soluble in water. Also soluble in dilute KOH Melting Point 225 °C
Formula C19H22FN3O3 Boiling Point 560.5 °C at 760 mmHg
Molecular Weight 359.4 Flash Point 292.8 °C
Transport Information N/A Appearance Pale yellow crystals
Safety 26-36/37 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 93106-60-6 (Enrofloxacin) Hazard Symbols IrritantXi
Synonyms

1-Cyclopropyl-6-fluoro-7-(4-ethyl-1-piperazinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylicacid;Alsir;BAY-Vp 2674;Baytril;Biofloxavet;CFPQ;Enrocin;Enrofan;Enrogil;Enroxil;N-Ethylciprofloxacin;N'-Ethylciprofloxacin;3-Quinolinecarboxylicacid, 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-;

Article Data 17

Enrofloxacin Synthetic route

5308-25-8

4-ethylpiperazine

86393-33-1

7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

93106-60-6

enrofloxacin

Conditions
ConditionsYield
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.316667h; Solvent; Temperature; Reagent/catalyst; Reflux;97%
at 150℃; for 0.416667h; Microwave irradiation;93%
With aluminum tri-bromide In ethanol at 75℃; for 4h; Reagent/catalyst; Solvent; Temperature;92%

1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid sodium salt

5308-25-8

4-ethylpiperazine

93106-60-6

enrofloxacin

Conditions
ConditionsYield
With aluminum (III) chloride In i-Amyl alcohol at 140℃; for 8h; Temperature;91.8%
131776-44-8

ditrimethylsilyl N-cyclopropyl-3-(4-ethyl-1-piperazinyl)anilinomethylenemalonate

93106-60-6

enrofloxacin

Conditions
ConditionsYield
90%
5308-25-8

4-ethylpiperazine

86393-33-1

7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

A

7-chloro-1-cyclopropyl-6-(4-ethyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

B

93106-60-6

enrofloxacin

Conditions
ConditionsYield
In water for 13h; Heating;A n/a
B 89%
74-96-4

ethyl bromide

93107-08-5

ciprofloxacin hydrochloride

93106-60-6

enrofloxacin

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; potassium iodide In water; acetonitrile at 20℃; for 12h;70%
5308-25-8

4-ethylpiperazine

98349-24-7

ethyl 2,4,5-trifluorobenzoylacetate

4637-24-5

N,N-dimethyl-formamide dimethyl acetal

765-30-0

Cyclopropylamine

93106-60-6

enrofloxacin

Conditions
ConditionsYield
Yield given. Multistep reaction;
86483-51-4

ethyl 2,4-dichloro-5-fluoro-benzoyl-acetate

93106-60-6

enrofloxacin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: acetic anhydride / 2 h / Heating
2: 92 percent / ethanol / 1 h / Ambient temperature
3: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C
4: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating
5: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C
View Scheme
86483-53-6

3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-ethylester

93106-60-6

enrofloxacin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C
2: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating
3: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C
View Scheme
86483-54-7

ethyl 1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate

93106-60-6

enrofloxacin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating
2: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C
View Scheme
86393-34-2

2,4-dichloro-5-fluorobenzoyl chloride

93106-60-6

enrofloxacin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 62 percent / pyridine / dioxane / 1.) 2 h, room temperature, 2.) 1 h, 70 - 80 deg C.
2: 85 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C
3: 92 percent / conc. H2SO4 / H2O; acetic acid / 1.5 h / Heating
4: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C
View Scheme
Multi-step reaction with 7 steps
1: Mg/ethanol, CCl4 / ethanol; toluene / 1.) 0 to -5 deg C, 2.) 12 h, room temperature
2: p-toluenesulfonic acid / H2O / 5 h / Heating
3: acetic anhydride / 2 h / Heating
4: 92 percent / ethanol / 1 h / Ambient temperature
5: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C
6: 93 percent / conc. H2SO4 / H2O / 1.5 h / Heating
7: 86 percent / dimethylsulfoxide / 2.5 h / 140 °C
View Scheme
Multi-step reaction with 2 steps
1.1: tributyl-amine / 1 h / 70 °C
1.2: 15 °C / 1520.1 Torr
2.1: cesium hydroxide / 5,5-dimethyl-1,3-cyclohexadiene / 125 - 130 °C
2.2: 8 h / 85 °C
View Scheme

Enrofloxacin Chemical Properties


IUPAC Name: 1-Cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid
Molecular Weight: 359.394683 [g/mol]
Molecular Formula: C19H22FN3O3
XLogP3: -0.2
H-Bond Donor: 1
H-Bond Acceptor: 7 
Index of Refraction: 1.634
Molar Refractivity: 92.8 cm3
Molar Volume: 259.3 cm3
Surface Tension: 62 dyne/cm
Density: 1.385 g/cm3
Flash Point: 292.8 °C
Enthalpy of Vaporization: 88.7 kJ/mol
Boiling Point: 560.5 °C at 760 mmHg
Vapour Pressure: 2.13E-13 mmHg at 25 °C
Water Solubility: 3400 mg/L at 25 °C
Appearance: Pale Yellow Crystals
Melting Point: 225 °C
Classification Code of Enrofloxacin (CAS NO.93106-60-6): Antibacterial [veterinary]; Antineoplastic agents; Drug / Therapeutic Agent; Mutation data
Product Categories: Antibiotics for Research and Experimental Use; Biochemistry; Quinolones (Antibiotics for Research and Experimental Use); Intermediates & Fine Chemicals; Pharmaceuticals; Veterinaries

Enrofloxacin Uses

 Enrofloxacin (CAS NO.93106-60-6) is widely used in the treatment of human disease. It is a bactericidal agent. The bactericidal activity of enrofloxacin is concentration dependent, with susceptible bacteria cell death occurring within 20-30 minutes of exposure. Enrofloxacin has demonstrated a significant post-antibiotic effect for both Gram-negative and Gram-positive bacteria and is active in both stationary and growth phases of bacterial replication.

Enrofloxacin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 200mg/kg (200mg/kg)   VMR, Veterinary Medical Review. Vol. 2, Pg. 87, 1987.
mouse LD50 oral 4336mg/kg (4336mg/kg)   VMR, Veterinary Medical Review. Vol. 2, Pg. 87, 1987.
rabbit LD50 oral 500mg/kg (500mg/kg)   VMR, Veterinary Medical Review. Vol. 2, Pg. 87, 1987.
rat LD50 oral 5gm/kg (5000mg/kg)   VMR, Veterinary Medical Review. Vol. 2, Pg. 87, 1987.

Enrofloxacin 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: 3
RTECS of Enrofloxacin (CAS NO.93106-60-6): VB1993650

Enrofloxacin Specification

 Enrofloxacin (CAS NO.93106-60-6), its Synonyms are 1,4-Dihydro-1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-4-oxo-3-quinolinecarboxylic acid ; 1-Cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ; BAY VP 2674 ; Enrofloxacine ; Enrofloxacino ; 3-Quinolinecarboxylic acid, 1,4-dihydro-1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-4-oxo- ; 3-Quinolinecarboxylic acid, 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo- .

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