73231-34-2 Usage
Veterinary antibiotics
Florfenicol is currently a commonly used veterinary antibiotic with a broad antibacterial spectrum and a strong antibacterial effect as well as a low the minimum inhibitory concentration (MIC). The antibacterial of florfenicol is about 15-20 times as high as that of chloramphenicol and the thiamphenicol. After administration through feed for 60 minutes, the drug concentration in the tissue can reach peak which can quickly control the disease with having characteristics such as being safe, non-toxic, no residue, and no risk for triggering aplastic anemia. Therefore, it is quite suitable for large-scale farms application. It is mainly used for the treatment of bovine respiratory disease caused by Pasteurella and Haemophilus. It has good efficacy in treating the cattle footrot disease cause by Fusobacterium, and can be also used for treating the infection diseases of pigs and chickens caused by sensitive strains as well as the bacterial disease of fish.
It is not easy for bacteria to evolve resistance against florfenicol: Because it has a fluorine atom which replaces the hydroxyl group on the molecular structure of thiamphenicol, thus effectively solving the drug resistant issue of chloramphenicol, and thiamphenicol. Bacteria which are resistant to thiamphenicol, chloramphenicol, amoxicillin, and quinolone remain sensitive to the chemicals.
Since chloramphenicol can result in severe adverse reactions such as aplastic anemia and immune suppression, it is banned from being applied in food animal production. Studies have demonstrated that: the major group in the chemical structure of chloramphenicol which causes aplastic anemia is para-nitro in the aromatic ring. Instead, florfenicol has the CH3SO4 which replaces the NO2 groups so that its chemical structure has been changed. In this case, its application to animal will not cause any adverse reactions such as aplastic anemia. Therefore, it is approved for application in more than a dozen of countries such as Japan, Mexico and China. Florfenicol is characterized by: a broad spectrum antibiotic; Salmonella, Escherichia coli, Proteus, Haemophilus, Actinobacillus pleuropneumoniae, Mycoplasma hyopneumoniae, Streptococcus Suis, swine Pasteurella, Bordetclla bronchiseptica, and Staphylococcus aureus are all sensitive to it. The drug is easy for absorbing and is widely distributed in the body and is quick-acting and long-acting formulations with no potential risk of causing aplastic anemia risks and thus having a better security. In addition, it has an affordable price which is cheaper than other drugs for prevention and treatment of respiratory diseases such as tiamulin, tilmicosin, and azithromycin. The cost of medication is easy for users to accept. Because of all these excellent characteristics, domestic florfenicol is widely applied and has currently become the first-choice drug for prevention and treatment of livestock respiratory diseases and gastrointestinal bacterial infection diseases.
Florfenicol is not suitable to be applied in combination with quinolones, penicillins, and cephalosporins, and it has no compatibility with ampicillin, sulfonamides, and furans.
The above information is edited by the lookchem of Dai Xiongfeng.
Pharmacological effects
Florfenicol binds tightly with the 50S subunit of the bacterial ribosome and block the transpeptidation reaction mediated by peptidyl transferase, and thereby suppressing the elongation process of the peptide chain; meanwhile selectively acts on the bacterial 70S ribosome receptors and changes, interferes with the function of peptidyl transferase enzyme. Therefore, it interferes with the bacterial protein synthesis based on dual mechanism.
Indications
Florfenicol can strongly interfere with the bacterial protein synthesis. It has a rapid absorption rate and is widely distributed in the body; it has long half-life without side effects such as aplastic anemia; not easy for bacteria to evolve drug resistance, and has no cross-resistance.
Florfenicol can be used for the treatment of the systemic infection of livestock and aquatic animals, and has significant efficacy on treating respiratory infections and intestinal infections.
Poultry: Escherichia coli disease, salmonellosis, infectious rhinitis, chronic respiratory disease, duck plague and other kinds of mixed infections caused by susceptible strains.
Animals: Mixed infections such as infectious pleurisy, asthma, streptococcal disease, Escherichia coli disease, salmonellosis, contagious pleuropneumonia, enzootic pneumonia, paratyphoid piglets yellow white diarrhea, edema disease, atrophic rhinitis, lung epidemic, red white diarrhea piglets, and agalactia syndrome occurred in animals such as pigs, cows, and sheep.
Crab: appendages ulcer disease, yellow gills, rotten gill, red legs and red fluorescent body inflammatory disease syndrome.
Turtle: red neck disease, furunculosis, shot-hole disease, skin fester disease, inflammatory bowel disease, mumps, and bacterial sepsis.
Frogs: cataract syndrome, ascites disease, sepsis, enteritis.
Fish: enteritis disease, ascites disease, vibriosis, Edward coli disease.
Eel: debonding septicemia (unique effect), Edward coli disease, red skin disease, inflammatory bowel disease.
Uses
Different sources of media describe the Uses of 73231-34-2 differently. You can refer to the following data:
1. It is a kind of antibacterial drug. It is used as the veterinary antimicrobial drugs for treating bacterial diseases of pigs, chickens and fish. It has good efficacy in treating the infection disease of pigs, chickens and fish induced by sensitive bacteria, especially for treating respiratory infections and intestinal infections.
2. Florfenicol is a fluorinated derivative of thiamphenicol. It is a protein synthesis inhibitor that inhibits bacterial protein synthesis by binding to ribosome 50S and 70S subunits. Florfenicol is used as an antibacterial.
Description
Florfenicol is a broad-spectrum fluorinated antibiotic and a derivative of thiamphenicol . It is active against human clinical isolates of enteric bacteria, including E. coli, Klebsiella, Enterobacter, Citrobacter, P. mirabilis, and Salmonella (MIC50s = 6.3-12.5 μg/ml). Florfenicol is also active against clinical isolates of various bovine and porcine respiratory tract pathogens, including P. multocida, A. pleuropneumoniae, and B. bronchiseptica (MIC50s = 0.25-4 μg/ml). It inhibits peptidyl transferase activity in 70S ribosomes isolated from E. coli when used at a concentration of 1 mM. Formulations containing florfenicol have been used in the treatment of infectious respiratory disease in cattle.
Chemical Properties
White or off-white crystalline powder, odorless. Easily soluble in dimethylformamide, soluble in methanol, slightly soluble in glacial acetic acid, very slightly soluble in water or chloroform.
Definition
ChEBI: Florfenicol is a carboxamide that is the N-dichloroacetyl derivative of (1R,2S)-2-amino-3-fluoro-1-[4-(methanesulfonyl)phenyl]propan-1-ol. A synthetic veterinary antibiotic that is used for treatment of bovine respiratory disease and foot rot; also used in aquaculture. It has a role as an antimicrobial agent. It is a sulfone, a secondary alcohol, an organofluorine compound, an organochlorine compound and a secondary carboxamide. It is functionally related to a dichloroacetic acid.
Preparation
Florfenicol is synthesised from thiamphenicol by replacing the 3-hydroxy group with fluorine, first synthesised at Schering in 1980. By replacing the hydroxy group, it was rationalised that chloramphenicol resistance via chloramphenicol acetyltransferase could be eliminated. Florfenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. It acts by binding to the 23S sub-unit of the 50S ribosome, inhibiting protein synthesis. Florfenicol has been extensively studied with over 400 literature citations.
Veterinary Drugs and Treatments
The drug is approved for use in cattle only (in the USA) for the
treatment of bovine respiratory disease (BRD) associated with
Pasteurella haemolytica, Pasteurella multocida, and Haemophilus
somnus.
Because florfenicol has activity against a wide range of microorganisms
(e.g., Mycoplasma), it may be useful for treating other
infections in cattle (or other species) as well, but specific data is
limited.
Check Digit Verification of cas no
The CAS Registry Mumber 73231-34-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,2,3 and 1 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 73231-34:
(7*7)+(6*3)+(5*2)+(4*3)+(3*1)+(2*3)+(1*4)=102
102 % 10 = 2
So 73231-34-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H14Cl2FNO2S/c1-19-8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)
73231-34-2Relevant articles and documents
Synthesis method of florfenicol
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Paragraph 0063-0065, (2021/03/24)
The invention discloses a synthesis method of florfenicol, which comprises the following steps: by using (4R,5R)-2-dichloromethyl-4,5-dihydro-5-[4-(methylsulfonyl)phenyl]-4-oxazolemethanol (compound Ifor short) as a reaction raw material, carrying out chlorination, fluorination and hydrolysis to obtain florfenicol. The method has the advantages of cheap and easily available raw materials, simpleprocess operation, environmental protection and no pollution, accords with the industrialization concept of green production, and has extremely high industrialization value.
Method for continuously preparing florfenicol based on micro-reaction system
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Paragraph 0053-0054; 0057-0061; 0065-0068; 0072-0075; ..., (2021/07/24)
The invention provides a method for continuously preparing florfenicol based on a micro-reaction system. The preparation method comprises the following steps: respectively pumping an organic solution of a raw material {(4R, 5R)-2-(dichloromethyl)-5-[4-(methylsulfonyl) phenyl]-4, 5-dihydrooxazole-4-yl} methanol and an organic solution of a fluorinating reagent into a micro-mixer for mixing; introducing into a first micro-channel reactor for continuous fluorination reaction, and concentrating; obtaining a crude product; dissolving the crude product in alcohol and water, pumping into a second microchannel reactor, carrying out continuous hydrolysis ring-opening reaction, and separating and purifying a reaction product to obtain a florfenicol product. According to the method provided by the invention, the reaction time is only several minutes, the yield of the product florfenicol is greater than 95%, the operation is convenient, continuous and controllable, the amplification effect is avoided, the efficiency of the technological process is high, and the method has a very good industrial application prospect.
Unified Strategy to Amphenicol Antibiotics: Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, and (+)-Thiamphenicol and Its (+)-3-Floride
Liu, Jinxin,Li, Yaling,Ke, Miaolin,Liu, Minjie,Zhan, Pingping,Xiao, You-Cai,Chen, Fener
, p. 15360 - 15367 (2020/11/30)
The asymmetric synthesis of (-)-chloramphenicol, (-)-azidamphenicol, and (+)-thiamphenicol and its (+)-3-floride, (+)-florfenicol, is reported. This approach toward the amphenicol antibiotic family features two key steps: (1) a cinchona alkaloid derived urea-catalyzed aldol reaction allows highly enantioselective access to oxazolidinone gem-diesters and (2) a continuous flow diastereoselective decarboxylation of thermally stable oxazolidinone gem-diesters to form the desired trans-oxazolidinone monoesters with two adjacent stereocenters that provide the desired privileged scaffolds of syn-vicinal amino alcohols in the amphenicol family.
