ChemicalBook--->CAS DataBase List--->62587-73-9

62587-73-9

62587-73-9 Structure

62587-73-9 Structure
IdentificationMore
[Name]

(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
[CAS]

62587-73-9
[Synonyms]

CEFSULODIN
Pyridinium, 4-(aminocarbonyl)-1-[[(6R,7R)-2-carboxy-8-oxo-7-[[(2R)-phenylsulfoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, inner salt
Pyridinium, 4-(aminocarbonyl)-1-[[2-carboxy-8-oxo-7-[(phenylsulfoacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, inner salt, [6R-[6α,7β(R*)]]-
(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
[Molecular Formula]

C22H20N4O8S2
[MDL Number]

MFCD00865072
[Molecular Weight]

532.55
[MOL File]

62587-73-9.mol
Chemical PropertiesBack Directory
[storage temp. ]

0-5°C
[CAS DataBase Reference]

62587-73-9(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
Hazard InformationBack Directory
[Description]

Cefsulodin is a semi-synthetic, third-generation cephalosporin antibiotic with a narrow spectrum of activity. It was first synthesized and patented by the Takeda Pharmaceutical Company in 1977. Cefsulodin has activity against Pseudomonas aeruginosa and Staphylococcus aureus but little activity against other bacteria. It is eliminated renally and has a serum half-life similar to ceftazidime and cefoperazone. Cefsulodin appears to be well tolerated and relatively free of any significant toxicity except for nausea and vomiting, which appear to be related to the infusion rate.
[Originator]

Pseudomonil,Ciba Geigy,W. Germany,1980
[Definition]

ChEBI: A pyridinium-substituted semi-synthetic, broad-spectrum, cephalosporin antibiotic.
[Uses]

Cefsulodin is a third generation cephalosporin antibiotic that has very specific activity against Pseudomonas aeruginosa. Cefuslodin is used in CIN (cefsulodin-Irgasan-novobiocin) agar to select for microorganisms such as E. coli. Cefsulodin is a substrate for rat Oatp1a4. It has been used to study multidrug resistance-associated protein 4 in efflux transport of prostaglandin E2 across the mouse blood-brain barrier. Cefsulodin is used to study the effect of expression, binding, and inhibition of PBP1 and other penicillin-binding proteins (PBPs) on bacterial cell wall mucopeptide synthesis.
[Manufacturing Process]

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.
[Therapeutic Function]

Antibiotic
[Antimicrobial activity]

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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