ChemicalBook--->CAS DataBase List--->52152-93-9

52152-93-9

52152-93-9 Structure

52152-93-9 Structure
IdentificationBack Directory
[Name]

Cefsulodine sodium
[CAS]

52152-93-9
[Synonyms]

Ulfar
sce129
ulfaret
tilmapor
pyocefal
cgp7174e
monaspor
pseudocef
cefomonil
takesulin
pseudomonil
Abbot 46811
abbott-46811
D-(-)-SCE-129
sulcephalosporin
Sodium cefsulodin
CEFSULODINE SODIUM
CEFSULONDIN SODIUM
Monosodium cefsulodin
CEFSULODIN SODIUM SALT
Cefsulodin SodiuM Hydrate
CEFSULODIN SODIUM SALT HYDRATE
Cefsulodin hydrate sodium salt
(6r-(6-alpha,7-beta(r*)))-odiumsal
Cefsulodin (SCE-129), Antibiotic for Culture Media Use Only
5-thio-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-,hydroxide,innersalt,monos
4-(aminocarbonyl)-1-((2-carboxy-8-oxo-7-((phenylsulfoacetyl)amino)-pyridiniu
cetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-,innersalt,mono
pyridinium,4-(aminocarbonyl)-1-[[(6r,7r)-2-carboxy-8-oxo-7-[[(2r)-phenylsulfoa
7-(D-α-Sulfophenylacetamido)ceph-3-em-3-(4'-carbamoylpyridinium)methyl-4-carboxylate sodium salt
(6R,7R)-3-[(4-Carbamoylpyridinio)methyl]-8-oxo-7-[(R)-2-phenyl-2-sulfoacetylamino]-5-thia-1-azabicyclo[4.2.0]octan-2-ene-2-carboxylate
(6R,7R)-3-[(4-Carbamoylpyridinio)methyl]-8-oxo-7-[(R)-2-phenyl-2-(sodiosulfo)acetylamino]-5-thia-1-azabicyclo[4.2.0]octan-2-ene-2-carboxylate
4-(AMinocarbonyl)-1-[[(6R,7R)-2-carboxy-8-oxo-7-[[(2R)-2-phenyl-2-sulfoacetyl]aMino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]Methyl]pyridiniuM
Sodium (6R,7R)-3-[(4-carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[[(2R)-2-phenyl-2-sulfonatoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
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, monosodium salt
hydrogen [6R-[6alpha,7beta(R*)]]-4-carbamoyl-1-[[2-carboxylato-8-oxo-7-(phenylsulphonatoacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium, monosodium 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, monosodium salt, [6R-[6a,7b(R*)]]-
Pyridinium, 4-(aminocarbonyl)-1-[[2-carboxy-8-oxo-7-[(phenylsulfoacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, hydroxide, inner salt, monosodium salt, [6R-[6α,7β(R*)]]-
[EINECS(EC#)]

257-692-4
[Molecular Formula]

C22H19N4O8S2.Na
[MDL Number]

MFCD00865072
[MOL File]

52152-93-9.mol
[Molecular Weight]

554.53
Chemical PropertiesBack Directory
[Melting point ]

175 C
[storage temp. ]

2-8°C
[solubility ]

H2O: 50 mg/mL, clear, light yellow
[form ]

powder or crystals
[color ]

Off-White to Pale Yellow
[Water Solubility ]

Soluble in water.
[Merck ]

13,1958
[Stability:]

Hygroscopic
[InChIKey]

REACMANCWHKJSM-DWBVFMGKSA-M
[EPA Substance Registry System]

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, monosodium salt (52152-93-9)
Hazard InformationBack Directory
[Uses]

A β lactam antibiotic.
[Uses]

betaadrenergic blocker
[Uses]

Cefsulodin is a third generation cephalosporin (C258750) antibiotic designed specifically for Pseudomonas Aeruginosa.
[Originator]

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

ChEBI: Cefsulodin sodium is an organic molecular entity.
[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.
[Brand name]

Cefomonil (TAP).
[Therapeutic Function]

Antibiotic
[Biological Activity]

cefsulodin, formerly named as sce-129, is a cephalosporin with a spectrum of antibacterial activity against staphylococcus aureus, pseudomonas aeruginosa, and most other gram-positive cocci [1]. cefsulodin shows little activity against other species of acinetobacter spp., pseudomonas, or members of the enterobacteriaceae [1]. cefsulodin is a β-lactam antibiotic that involved in lysing actively-growing e. coli by specifically binding to the intermembrane proteins, penicillin-binding proteins 1a and b, whose transglycosylase and transpeptidase activities are involved in cell elongation and septation [2].cefsulodin was active against p. aeruginos. cefsulodin was active against penicillinase-producing strains of s. aureus. the mics of cefsulodin for pseudomonas aeruginosa and its mutants pseudomonas aeruginosa pao4089 were 0·78 and 12· mg/l [3]. cefsulodin was active in minimum inhibitory concentrations (mics) of 0.5 to 64 μg/ml. cefsulodin was active against p. diminuta, p. maltophilia, p. paucimobilis, and p. pseudoalcaligenes with mics of 1-32 μg/ml. cefsulodin was not hydrolyzed by the β-lactamase induced in p. aeruginosa by growth in the presence of benzylpenicillin and was a poor substrate for β-lactamases from enterobacter cloacae and proteus morganii [4].
[References]

[1] barry a l, jones r n, thornsberry c. cefsulodin: antibacterial activity and tentative interpretive zone standards for the disk susceptibility test[j]. antimicrobial agents and chemotherapy, 1981, 20(4): 525-529.
[2] jacoby g h, young k d. cell cycle-independent lysis of escherichia coli by cefsulodin, an inhibitor of penicillin-binding proteins 1a and 1b[j]. journal of bacteriology, 1991, 173(1): 1-5.
[3] bryan l e, kwan s, godfrey a j. resistance of pseudomonas aeruginosa mutants with altered control of chromosomal beta-lactamase to piperacillin, ceftazidime, and cefsulodin[j]. antimicrobial agents and chemotherapy, 1984, 25(3): 382-384.
[4] king a, shannon k, phillips i. in vitro antibacterial activity and susceptibility of cefsulodin, an antipseudomonal cephalosporin, to beta-lactamases[j]. antimicrobial agents and chemotherapy, 1980, 17(2): 165-169.
Safety DataBack Directory
[Hazard Codes ]

Xi,Xn
[Risk Statements ]

36/37/38-42/43-20/21/22
[Safety Statements ]

22-26-36/37-45-36
[WGK Germany ]

2
[RTECS ]

UU1785000
[TSCA ]

Yes
[HS Code ]

29419059
[Toxicity]

LD50 in mice (mg/kg): >4000 i.p.; >15000 orally (Bryskier)
Questions And AnswerBack Directory
[Cephalosporins]

Cefsulodine sodium is a cephalosporin antibiotic, its antimicrobial spectrum is narrow, because it has good permeability to the outer layer of the cell wall of Pseudomonas aeruginosa , and it has a high affinity on penicillin-binding protein LA, LB and Ⅲ and thus it has strong bactericidal inhibition effect on the formation of the cell wall peptidoglycan , it has a strong and specific bactericidal effect on P. aeruginosa , the MIC is 1.5μg/ml, and it has high stability on β-lactamase produced by itself . Its antimicrobial activity against Pseudomonas aeruginosa is stronger than cefoperazone, methyl benzyl amoxicillin (10 times), carbenicillin, piperacillin and hydroxyl ampicillin (16 to 32-fold) , and its antimicrobial activity against Pseudomonas aeruginosa is equal to aminoglycoside antibiotics such as gentamicin, dibekacin . And there is no cross-resistance.After intramuscular or intravenous administration 0.5g, 15min respectively ,it achieves the maximum blood concentration of 37.2μg/ml, and the concentration of the drug increases with the increase of the dose . It can be quickly distributed to the kidneys, blood plasma, lung, heart, digestive tract, liver and spleen, and it can go access to sputum, wound exudate, amniotic fluid and breast milk. PBP is 70%, t1/2 is 1.5h, it is mainly excreted in the urine, 6h after treatment the urine excretion rate is 60% to 70%, metabolites with antibacterial activity are not found in the urine . In renal dysfunction patients , plasma concentration increases, half-life extends and urinary excretion rate decreases.
Sodium cefsulodin is clinically used for the treatment of respiratory tract infections caused by Pseudomonas aeruginosa, pyelonephritis, cystitis, peritonitis, septicemia, prostatitis, burns, wounds and otitis media secondary infection, corneal ulcers, especially penicillin and aminoglycosides antibiotic treatment ineffective Pseudomonas aeruginosa infection.
Adverse reactions occurring rate is approximately 1.3%, it is similar to other cephalosporins. Occasionally allergic reactions occur, such as rash, urticaria.There are gastrointestinal reactions. Injection site is painful, intravenous injection causes phlebitis, mildly elevated serum transaminases , few visible proteinuria; there are also visible thrombocytopenia, increased eosinophils; rare thrombocytopenia, vitamin deficiency and the like.
Patients allergic to the chemicalsare are banned .Patients allergic to penicillin,and cephalosporin , having history of allergy diseases, allergic bodies, severe renal dysfunction, and pregnant women should use with caution. Cefsulodine sodium together with diuretics, aminoglycosides can increase renal toxicity. Check liver function, kidney function and blood at regular intervals .
The above information is edited by the chemicalbook of Tian Ye.
[Category]

Toxic substances
[Toxicity grading]

Low toxicity
[Acute toxicity]

Intravenous-rat LD50: 3030 mg/kg; Intravenous-Mouse LD50: 3780 mg/kg.
[Flammability and hazard characteristics]

Thermal decomposition produces toxic nitrogen oxides, sulfur oxides, sodium oxide fumes.
[Storage Characteristics]

Ventilated, low-temperature ,dry storeroom.
[Extinguishing agent]

Water, carbon dioxide, foam, powder.
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