(6R,7R)-3-[(4-Carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[[(2R)-2-phenyl-2-sulfoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;cCAS 62587-73-9
(6R,7R)-3-[(4-Carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[[(2R)-2-phenyl-2-sulfoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical Properties
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storage temp.
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0-5°C
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CAS DataBase Reference
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62587-73-9(CAS DataBase Reference)
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Hazard Codes
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Xn
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Risk Statements
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20/21/22-36/37/38
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Safety Statements
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26-36
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(6R,7R)-3-[(4-Carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[[(2R)-2-phenyl-2-sulfoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Usage And Synthesis
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Originator
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Pseudomonil,Ciba Geigy,W. Germany,1980
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Definition
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ChEBI: A pyridinium-substituted semi-synthetic, broad-spectrum, cephalosporin antibiotic.
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Manufacturing Process
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0.514 g (4 x 10-3 mol) of 7-(α-sulfophenylacetamido)cephalosporanic acid, 0.466 g (3 x 10-3 mol) of isonicotinamide and 2.0 g (2.06 x 10-3 mol) of potassium thiocyanate were dissolved in 2.5 ml of water. The resulting solution was allowed to stand and heated for 20 hours in a thermostat kept at 50°C and then directly purified by chromatography on an Amberlite XAD-2 column (16 x 880 mm). Subsequently, the fractions containing the cephalosporins were collected and subjected to freeze-drying to obtain 270 g of the title product in the form of a pale yellowish white powder. The product is usually used as the sodium salt.
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Therapeutic Function
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Antibiotic
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Antimicrobial activity
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A semisynthetic parenteral cephalosporin supplied as the sodium salt. Activity against Ps. aeruginosa contrasts strikingly with poor activity against many other organisms. Anaerobic Gram-negative rods, Gram-positive rods and cocci are all resistant. It is stable to many β-lactamases, including the Ps. aeruginosa chromosomal enzyme, and is a poor substrate for the enzymes of Enterobacter spp. and Morg. morganii. It is slowly hydrolyzed by TEM β-lactamases and more rapidly by the enzymes of some carbenicillin-resistant strains of Ps. aeruginosa, with which distinct inoculum effects may be seen.
A 500 mg intravenous bolus dose achieves a plasma concentration of c. 70 mg/L at the end of the injection; the corresponding intramuscular dose achieves a peak concentration of around 15 mg/L. The plasma half-life is 1.5 h. About 15-30% is protein bound.
There is some metabolism of the drug, but the main route of excretion is via the kidneys, most appearing in the urine in the first 6 h. The plasma half-life is linearly related to creatinine clearance, rising to a mean of 10-13 h in patients where clearance was <10 mL/min, falling to around 2 h on hemodialysis.
It is well tolerated, apart from nausea and vomiting in some subjects. It has been used in severe pseudomonas infections, usually in combination with an aminoglycoside, but treatment has been complicated on a number of occasions by the emergence of resistance or superinfection. It is available in Japan.
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Company Informations:
Hunan Yunbang Pharmaceutical Co., Ltd.
(
Yunbangpharm)
located in Changsha High-tech Industrial Park, Hunan. It is a high-tech enterprise specializing in the research and development, production and sales of Pharmaceutical raw materials, Pharmaceutical intermediates(API) and Fine chemicals. Based in China, Yunbangpharm has been providing suitable solutions for many domestic,foreign pharmaceutical companies and traders. Excellent quality, good reputation and authentic price have won the praise of the majority of customers.
The company adheres to the corporate tenet of "We do not produce medicines, but help pharmaceutical companies make good medicines".
We can provide customers with customized processing, research and development services;
We can develop high-end Pharmaceutical and chemical products with high technical difficulties,high barriers and unique production processes;
We can provide 100 grams Grade, kilograms, and hundred kilograms of raw material pharmaceutical intermediates and other products.
We can perform -100°C to 300°C reaction.
R&D strength is the company's core competitiveness.Yunbangpharm has maintains a good cooperation relationship with many Universities and Research institutes locally, which can quickly transform R&D results into industrial production.
Our goal : To achieve the integrated upgrade of
P
harmaceutical intermediates, raw materials and high-end chemical products, adhere to "serving pharmaceutical companies, creating
our
brands" to provide customers with high-quality and low-cost pharmaceutical and chemical products, realizing Win-win cooperation and common development.