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Enrofloxacin

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Enrofloxacin Basic information
Brand Name(s) in US Veterinary fluoroquinolone antimicrobial agents Reasonable compatibility Incompatibility Side effects Precautions Uses
Product Name:Enrofloxacin
Synonyms:1,4-dihydro-1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-4-oxo-3-quinoli;ROFLOXACIN BASE;enrofloxacin Baytril;Enorofloxacin hydrochloride;ENROFLOXACIN MM(CRM STANDARD);ENROFLOXACIN 99%;EnrofloxacinBaseCpv2000;Enrofloxacinebase
CAS:93106-60-6
MF:C19H22FN3O3
MW:359.39
EINECS:618-911-2
Product Categories:Veterinaries;Antibiotics for Research and Experimental Use;Biochemistry;Quinolones (Antibiotics for Research and Experimental Use);Intermediates & Fine Chemicals;Pharmaceuticals;Antibiosis;BAYTRIL;API;Heterocycles;93106-60-6
Mol File:93106-60-6.mol
Enrofloxacin Structure
Enrofloxacin Chemical Properties
Melting point 225 °C
Boiling point 560.5±50.0 °C(Predicted)
density 1.385±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,2-8°C
solubility Chloroform (Slightly), Methanol (Very Slightly, Heated)
pka6.43±0.41(Predicted)
form powder or crystals
color Pale Yellow to Light Beige
Water Solubility Soluble in chloroform. Slightly soluble in water. Also soluble in dilute KOH
Merck 14,3592
BRN 5307824
InChIInChI=1S/C19H22FN3O3/c1-2-21-5-7-22(8-6-21)17-10-16-13(9-15(17)20)18(24)14(19(25)26)11-23(16)12-3-4-12/h9-12H,2-8H2,1H3,(H,25,26)
InChIKeySPFYMRJSYKOXGV-UHFFFAOYSA-N
SMILESN1(C2CC2)C2=C(C=C(F)C(N3CCN(CC)CC3)=C2)C(=O)C(C(O)=O)=C1
CAS DataBase Reference93106-60-6(CAS DataBase Reference)
EPA Substance Registry System3-Quinolinecarboxylic acid, 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo- (93106-60-6)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/37-24/25
WGK Germany 3
RTECS VB1993650
HS Code 29339900
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Resp. Sens. 1
Skin Sens. 1
Hazardous Substances Data93106-60-6(Hazardous Substances Data)
ToxicityLD50 in male, female mice (mg/kg): >5000, 4336 orally; ~200, ~200 i.v.; in male rats, male rabbits (mg/kg): >5000, 500-800 orally (Altreuther)
Enrofloxacin Usage And Synthesis
Brand Name(s) in USBaytril
Veterinary fluoroquinolone antimicrobial agentsEnrofloxacin and sarafloxacin, danofloxacin, difloxacin, ofloxacin, norfloxacin, orbifloxacin are commonly used third-generation fluoroquinolone broad-spectrum antimicrobial agents in veterinary clinic at present , is ethyl compound of ciprofloxacin, also known as ethyl ciprofloxacin, ethyl ciprofloxacin, norfloxacin, is effective on Gram-negative bacteria, Gram-positive bacteria and mycoplasma, its antibacterial activity is significantly superior to norfloxacin, the effect on mycoplasma is stronger than tylosin and Tiamulin Fumarate. This product is oral, intramuscular and subcutaneous injection, and is easily absorbed, widely distributed in vivo, in addition to the central nervous system, the concentration of the drug in other organizations, almost all are higher than the blood concentration. De ethylation in vivo, mainly produced active metabolite ciprofloxacin, but different among the animals metabolism are larger, birds, dogs, rabbits and cattle body's metabolic rates are high, horses and pigs body's metabolic rates are lower. Clinically Enrofloxacin is used for the treatment of various mycoplasma disease, and respiratory system, digestive system and urogenital system infections, skin infections and sepsis caused by E. coli, Salmonella, Haemophilus, Erysipelas bacillus, Staphylococcus, Streptococcus etc. Especially suitable for mixing infections caused by a variety of bacteria.
Spatial structure formulae diagram of Enrofloxacin
Spatial structure formulae diagram of Enrofloxacin
The above information is edited by the chemicalbook of Liu Yujie.
Reasonable compatibility1. Cooperated application of Enrofloxacin with aminoglycoside (gentamicin), third-generation cephalosporins (cefotaxime, ceftriaxone) and penicillin, colistin, may have synergistic antibacterial effect on certain bacteria (especially Pseudomonas aeruginosa or Enterobacteriaceae), in addition to penicillin-type drugs, due to enhanced toxicity, when in combination, need to reduce the dose, and administered separately.
2. Antibacterial activity of Enrofloxacin combined with apramycin enhanced, showed a synergistic effect. The reason was that antibacterial mechanism of apramycin was to specifically hinder biosynthesis of bacterial protein, and thus achieved effect on inhibiting and killing bacteria, while Enrofloxacin could specifically act on subunit A of bacterial DNA gyrase, inhibiting its activity, affecting DNA melting and sealing chain, both of combination had double blocking effect on bacterial replication and translation process.
3. at the same day were successively mixed to drink with colistin sulfate, can improve the efficacy of Enrofloxacin on chicken bacterial disease. and compatibility with SD silver used for the topical treatment of otitis in dogs.
Reference data: Zheng Hugong, Cui Yaoming editor. reasonable compatibility use of veterinary, Zhengzhou: Henan Science and Technology Press, 2009.
Incompatibility1. Enrofloxacin can inhibit metabolism of theophylline and caffeine, make the blood concentration increase, thereby causing toxic reactions.
2. Combined with anticholinergic drugs (atropine, 654-2) and H2 receptor antagonists (cimetidine, famotidine), making the bioavailability of Enrofloxacin reduce.
3. Enrofloxacin has a role in inhibiting liver drug enzymes, in combination with drugs metabolized in the liver such as erythromycin, lincomycin, etc. making its clearance decrease, blood concentration increased.
4. antacids may reduce absorption of Enrofloxacin in the gastrointestinal tract, not suitable for simultaneous use.
5. mixed with strongly acidic liquid and the strong alkaline liquid and precipitated.
6. Enrofloxacin and metoclopramide occur chemical changes, easy to turn into muddy, should not be mixed injection.
Side effectsToxicity of Enrofloxacin is less, safe for clinical use. Therapeutic doses have non-teratogenic and mutagenic effect. Can make young animals cartilage occur turbid, causing lameness and pain. Digestive system reactions are vomiting, abdominal pain and bloating. Skin reactions are erythema, pruritus, urticaria and photosensitivity reactions, etc.
Precautions1. Enrofloxacin aqueous solution was met with light and easy to change color and decompose, should be kept in dark place.
2. Drug-resistant strains of the product showed an increasing trend, not used at sub-therapeutic doses for long-term.
3. Antacids can inhibit the absorption of this product, should be avoided drinking at the same time.
4. In clinical application, can appropriately adjust dosage based on disease, concentration range of drinking water in poultry, per liter of water, added 25 to 100 mg.
5. withdrawal period of chicken is 8 days. Disabled in egg producing period of laying hen.
6. chicks are very sensitive to Enrofloxacin injection, had many poisoning report, the dose should be strictly controlled.
Uses1. Antimicrobial, for bacteria and mycoplasma infection.
2. New veterinary antimicrobial drugs, broad-spectrum, high efficiency, has special effects on Gram-positive and Gram-negative bacteria and mycoplasma.
Chemical PropertiesPale Yellow Crystals
UsesFluorinated quinolone antibacterial
UsesEnrofloxacin is a broad spectrum antibiotic bactericidal agent used in veterinary medicine to treat animals afflicted with certain bacterial infections.
DefinitionChEBI: A quinolinemonocarboxylic acid that is 1,4-dihydroquinoline-3-carboxylic acid substituted by an oxo group at position 4, a fluoro group at position 6, a cyclopropyl group at position 1 and a 4-ethylpiperazin-1-yl group at position 7. It is a veterinary ant bacterial agent used for the treatment of pets.
Brand nameBaytril (Bayer).
Synthesis
1-Ethylpiperazine

5308-25-8

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

86393-33-1

Enrofloxacin

93106-60-6

The reaction was carried out with 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1a, 1 mmol) and N-ethylpiperazine (2y, 1.5 mmol) by adding n-FZSA (0.06 g) as a catalyst, and the reaction was heated under reflux conditions in H2O (5 ml). The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the catalyst was separated using an external magnet and washed with hot ethanol (5 mL). Subsequently, the reaction mixture was cooled to room temperature. The precipitated solid was collected by filtration and recrystallized with methanol to afford the target product 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid in a high yield of 96%.

Veterinary Drugs and TreatmentsEnrofloxacin is approved for use in dogs and cats (oral only) for the management of diseases associated with bacteria susceptible to enrofloxacin. Because of the dosage restriction (5 mg/kg) for cats, enrofloxacin is generally used in this species only for the most susceptible bacterial infections. It is also been approved for use in cattle (not dairy cattle or veal calves).
References[1] Letters in Organic Chemistry, 2018, vol. 15, # 9, p. 739 - 746
[2] Russian Journal of General Chemistry, 2016, vol. 86, # 12, p. 2865 - 2869
[3] Zh. Obshch. Khim., 2016, vol. 86, # 12, p. 2865 - 2869,5
Tag:Enrofloxacin(93106-60-6) Related Product Information
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