Cefetamet pivoxil
Catalog Number: BT-253089
CAS Number: 111696-23-2
Molecular Formula: C20H26ClN5O7S2
Molecular Weight: 548 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Cefetamet pivoxil is a prodrug of cefetamet, a third-generation cephalosporin antibiotic. It is used to treat a wide range of bacterial infections, including respiratory tract infections, urinary tract infections, and skin and soft tissue infections. Cefetamet pivoxil is a potent and broad-spectrum antibiotic that has been widely used in medical, environmental, and industrial research.
Properties
CAS Number
111696-23-2
Product Name
Cefetamet pivoxil
IUPAC Name
2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride
Molecular Formula
C20H26ClN5O7S2
Molecular Weight
548 g/mol
InChI
InChI=1S/C20H25N5O7S2.ClH/c1-9-6-33-16-12(23-14(26)11(24-30-5)10-7-34-19(21)22-10)15(27)25(16)13(9)17(28)31-8-32-18(29)20(2,3)4;/h7,12,16H,6,8H2,1-5H3,(H2,21,22)(H,23,26);1H/b24-11-;/t12-,16-;/m1./s1
InChI Key
XAAOHMIKXULDKJ-LZRHLYMTSA-N
SMILES
CC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)OCOC(=O)C(C)(C)C.Cl
Synonyms
7-(2 (2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-desacetoxyceph-3-em-4-carboxylic acid pivaloyloxymethyl ester
cefetamet pivaloyloxymethyl ester
cefetamet pivoxil
cefetamet pivoxyl
Ro 15-8075
Ro-15-8075
cefetamet pivaloyloxymethyl ester
cefetamet pivoxil
cefetamet pivoxyl
Ro 15-8075
Ro-15-8075
Canonical SMILES
CC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)OCOC(=O)C(C)(C)C.Cl
Isomeric SMILES
CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N/OC)/C3=CSC(=N3)N)SC1)C(=O)OCOC(=O)C(C)(C)C.Cl
Method of Synthesis or Extraction
Cefetamet pivoxil is synthesized by the reaction of cefetamet hydrochloride with pivalic acid anhydride in the presence of a base. The reaction yields cefetamet pivoxil, which is a prodrug that is rapidly hydrolyzed in vivo to release cefetamet. The efficiency and yield of the synthesis process depend on the reaction conditions, such as the temperature, pH, and reaction time. The environmental and safety considerations of the synthesis process include the use of hazardous chemicals, such as pivalic acid anhydride, which can cause skin and eye irritation and respiratory problems.
Chemical Structure and Biological Activity
Cefetamet pivoxil has a chemical formula of C21H28N6O8S2 and a molecular weight of 592.62 g/mol. The chemical structure of cefetamet pivoxil consists of a beta-lactam ring, which is responsible for its antibacterial activity, and a pivaloyloxymethyl group, which is responsible for its prodrug properties. The mechanism of action of cefetamet pivoxil involves the inhibition of bacterial cell wall synthesis by binding to penicillin-binding proteins. The biological targets of cefetamet pivoxil include Gram-positive and Gram-negative bacteria, such as Streptococcus pneumoniae, Haemophilus influenzae, and Escherichia coli. The bioactivity and potency of cefetamet pivoxil depend on the bacterial strain, the dose, and the route of administration.
Biological Effects
Cefetamet pivoxil has several biological effects on cell function and signal transduction. It can disrupt bacterial cell wall synthesis, leading to cell lysis and death. It can also induce the production of reactive oxygen species, which can damage bacterial DNA and proteins. The potential therapeutic effects of cefetamet pivoxil include the treatment of bacterial infections and the prevention of antibiotic resistance. The potential toxic effects of cefetamet pivoxil include allergic reactions, gastrointestinal disturbances, and liver and kidney toxicity.
Applications
Cefetamet pivoxil has several applications in medical, environmental, and industrial research. In medical research, cefetamet pivoxil has been used in drug development, clinical trials, and findings. It has been found to be effective in the treatment of respiratory tract infections, urinary tract infections, and skin and soft tissue infections. The benefits of cefetamet pivoxil include its broad-spectrum activity, its low toxicity, and its ease of administration. The potential side effects of cefetamet pivoxil include allergic reactions, gastrointestinal disturbances, and liver and kidney toxicity. In environmental research, cefetamet pivoxil has been studied for its effects on ecosystems, its role in pollution management, and its sustainability and environmental impact. It has been found to have low toxicity to aquatic organisms and to degrade rapidly in the environment. In industrial research, cefetamet pivoxil has been used in manufacturing processes, improving product quality and efficiency, and health and safety considerations. It has been found to be a cost-effective and efficient antibiotic for industrial applications.
Future Perspectives and Challenges
The current limitations in the use and study of cefetamet pivoxil include the emergence of antibiotic resistance, the potential for toxic effects, and the need for more research on its environmental impact. Possible solutions and improvements include the development of new antibiotics, the use of combination therapy, and the implementation of sustainable and environmentally friendly manufacturing processes. Future trends and prospects in the application of cefetamet pivoxil in scientific research include the development of new formulations, the exploration of new therapeutic targets, and the integration of cefetamet pivoxil into personalized medicine.
Conclusion:
Cefetamet pivoxil is a potent and broad-spectrum antibiotic that has several applications in medical, environmental, and industrial research. Its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges have been discussed in this paper. Cefetamet pivoxil has the potential to be a valuable tool in the fight against bacterial infections, but its use and study must be carefully monitored to ensure its safety and efficacy.
Conclusion:
Cefetamet pivoxil is a potent and broad-spectrum antibiotic that has several applications in medical, environmental, and industrial research. Its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges have been discussed in this paper. Cefetamet pivoxil has the potential to be a valuable tool in the fight against bacterial infections, but its use and study must be carefully monitored to ensure its safety and efficacy.
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