Ceftiofur sodium CAS 104010-37-9

Introduction：Basic information about Ceftiofur sodium CAS 104010-37-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Ceftiofur sodium Basic information

• Product Name: Ceftiofur sodium
• Synonyms: (6R-(6alpha,7beta(Z))-7-(((2-Amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((2-furanylcarbonyl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt;naxcel;u-64279e;CEFTIOFUR SODIUM;ceftiofur sodium salt;SODIUM CEFTIOFUR;Ceftiofur Sodic;5-Thia-1-azabicyclo4.2.0oct-2-ene-2-carboxylic acid, 7-(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetylamino-3-(2-furanylcarbonyl)thiomethyl-8-oxo-, monosodium salt, (6R,7R)-
• CAS: 104010-37-9
• MF: C19H18N5NaO7S3
• MW: 547.55
• EINECS: 680-655-2
• Product Categories: Pharmaceutical intermediate;Antibiotics;APIs;cephalosporins antibiotics;veterinary drugs;104010-37-9
• Mol File: 104010-37-9.mol

Ceftiofur sodium Chemical Properties

• Melting point: >185°C (dec.)
• RTECS: XI0367360
• storage temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• solubility: Freely soluble in aqueous solution
• form: Solid
• color: Pale Yellow
• InChIKey: RFLHUYUQCKHUKS-JUODUXDSSA-M
• SMILES: C(C1=C(CS[C@]2([H])[C@H](NC(=O)/C(/C3N=C(N)SC=3)=N\OC)C(=O)N12)CSC(C1OC=CC=1)=O)(=O)O.[NaH] |&1:5,7,r|

Safety Information

• WGK Germany: 3
• HS Code: 2941906000

Ceftiofur sodium Usage And Synthesis

Description

Ceftiofur sodium is the sodium salt of ceftiofur, which belongs to the third generation cephalosporin antibiotics, for the first time in 1988 it was listed in the United States. Chemical properties are stabie, appearance is light yellow to white crystalline powder, aqueous solution has a shorter retention time, it should be diluted into a solution before use.
Ceftiofur has a broad antimicrobial spectrum , it has a strong antibacterial activity, it has a strong antibacterial activity against Gram-positive bacteria, Gram-negative bacteria, and some anaerobic bacteria ,its antibacterial activity is similar to or weaker than the first-generation cephalosporins against Gram-positive bacteria, it has a strong antibacterial activity against Gram-negative bacteria such as E. coli, Salmonella, Pasteurella and so on. It is used for a variety of respiratory, urinary tract and other infections caused by sensitive bacteria, especially for the prevention and treatment of early death of chicks caused by E. coli, Salmonella, Pseudomonas aeruginosa, Staphylococcus aureus , E. coli yellow dysentery of 1 piglets and wound infections caused by cutting the umbilical cord, ear numbers, cutting teeth, tails and others,pleuropneumoniae and bovine bronchial pneumonia caused by Haemophilus and Actinobacillus, generally it does not apply to cows and goats mastitis treatment . Some researchers have done ceftiofur sodium inhibition tests for thousands strains of pathogens isolated by veterinary clinically, the results show that the drug is one of the most active anti-bacterial drugs, it has a strong antibacterial activity against Escherichia coli, p.multocida and p.haemolytica ,Bacillus typhosus, Streptococcus ; it also has a good effect on Pseudomonas aeruginosa, Enterobacter, anaerobic bacteria. It is used for the treatment of respiratory disease of sheep,horses, cattle, pigs (pleuropneumonia),and the treatment of pets, day-old broiler infectious diseases. This product has characteristics such as complete intramuscular absorption and long elimination half-life period.
The above information is edited by the chemicalbook of Tian Ye.

Chemical Properties

White or light yellow crystalline powder

Uses

Ceftiofur sodium is resistant to the antibiotic resistance enzyme beta-lactamase, and has activity against Gram-positive and Gram-negative bacteria. E. coli strains resistant to ceftiofur have been reported. The bactericidal activity of ceftiofur results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins. The PBPs are transpeptidases which are vital in peptidoglycan biosynthesis. Therefore, their inhibition prevents this vital cell wall component from being properly synthesized.

Indications

Ceftiofur sodium is a third-generation broad-spectrum cephalosporin (β-lactam antibiotic) which is effective against Gram-positive, Gram-negative, anaerobic, and β-lactamase producing bacteria. It belongs to antibiotic medicines for the treatment of swine bacterial respiratory infection.

Definition

ChEBI: Ceftiofur sodium is an organic molecular entity.

Brand name

Naxcel

Side effects

Adverse reactions to Ceftiofur sodium are rare with intramuscular antimicrobial treatment with ceftiofur hydrochloride at a dose of 2.2 mg/kg. During the first day, the mare showed no signs of drug side effects. However, 24 hours later, during the second application, the patient developed incoordination, dizziness and loss of balance. At the same time, dexamethasone was given. Signs returned and the mare returned to normal after the reaction. Treatment with ceftiofur was changed to enrofloxacin and the animal recovered completely. These drug reactions are not common in the day-to-day work of equine clinical practitioners, but they are of great concern to owners and veterinarians^[1].

Veterinary Drugs and Treatments

Labeled indications for ceftiofur sodium:
In cattle for treatment of bovine respiratory disease (shippingfever, pneumonia) associated with Mannheimia haemolytica,Pasteurella multocida and Histophilus somni. It is also indicatedfor treatment of acute bovine interdigital necrobacillosis (foot rot,pododermatitis) associated with Fusobacterium necrophorum andBacteroides melaninogenicus.
In swine for treatment/control of swine bacterial respiratorydisease (swine bacterial pneumonia) associated with Actinobacillus(Haemophilus) pleuropneumoniae, Pasteurella multocida, Salmonellacholeraesuis and Streptococcus suis.
In sheep/goats for treatment of sheep/caprine respiratory disease(sheep/goat pneumonia) associated with Mannheimia haemolyticaand Pasteurella multocida.
In horses for treatment of respiratory infections in horses associatedwith Streptococcus zooepidemicus.In dogs for the treatment of canine urinary tract infections associatedwith E. coli and Proteus mirabilis.
In day old chicks/poults for the control of early mortality, associatedwith E. coli organisms susceptible to ceftiofur.
Ceftiofur sodium has also been used in an extra-label mannerin a variety of veterinary species (see Doses) to treat infections thatlikely to be susceptible to a 3rd generation cephalosporin.

Mode of action

Ceftiofur Sodium is the sodium salt form of ceftiofur, a semisynthetic, beta-lactamase-stable, broad-spectrum, third-generation cephalosporin with antibacterial activity. Ceftiofur binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

References

[1] GABRIELA D?WICH PRADELLA . Ceftiofur Side Effect in a Mare–Case Report[J]. Journal of Equine Veterinary Science, 2020, 95: Article 103295. DOI:10.1016/j.jevs.2020.103295.