[6R-[6α,7β(R*)]]-Hydrogen-4-carbamoyl-1-[[2-carboxylato-8-oxo-7-(phenylsulfonatoacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium, Mononatriumsalz

Bezeichnung:[6R-[6α,7β(R*)]]-Hydrogen-4-carbamoyl-1-[[2-carboxylato-8-oxo-7-(phenylsulfonatoacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium, Mononatriumsalz

CAS-Nr52152-93-9

Englisch Name:cefsulodin sodium salt

CBNumberCB5270251

SummenformelC22H19N4O8S2.Na

Molgewicht554.53

MOL-Datei52152-93-9.mol

Synonyma

[6R-[6α,7β(R*)]]-Hydrogen-4-carbamoyl-1-[[2-carboxylato-8-oxo-7-(phenylsulfonatoacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium, Mononatriumsalz

[6R-[6α,7β(R*)]]-Hydrogen-4-carbamoyl-1-[[2-carboxylato-8-oxo-7-(phenylsulfonatoacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium, Mononatriumsalz physikalisch-chemischer Eigenschaften

Schmelzpunkt	175 C
storage temp.	Inert atmosphere,Store in freezer, under -20°C
Löslichkeit	H₂O: 50 mg/mL, clear, light yellow
Aggregatzustand	powder or crystals
Farbe	Off-White to Pale Yellow
Wasserlöslichkeit	Soluble in water.
Merck	13,1958
Stabilität	Hygroscopic
InChIKey	REACMANCWHKJSM-DWBVFMGKSA-M
EPA chemische Informationen	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)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-42/43-20/21/22
S-Sätze:	22-26-36/37-45-36
WGK Germany	2
RTECS-Nr.	UU1785000
TSCA	Yes
HS Code	29419059
Toxizität	LD50 in mice (mg/kg): >4000 i.p.; >15000 orally (Bryskier)

Gefahreninformationscode (GHS)

cefsulodin sodium salt Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Cefsulodin was synthesized by Takeda Chemicals Industries in 1974 by introducing the sulfobenzyl group, the same moiety as in sulbenicillin, at the 7 position of the cephem nucleus. Its side chain at the 3 position is similar to that of cephaloridine except for the carbamoyl group. The introduction of these hydrophilic groups increases the activity against Pseudomonas aeruginosa, but it markedly decreases it against gram-positive and other gramnegative bacteria. Therefore cefsulodin is used as a specific antibiotic against infections caused by the opportunistic pathogen P. aeruginosa.
Originator
Pseudomonil,Ciba Geigy,W. Germany,1980
Verwenden
Cefsulodin is most commonly used in CIN agar to select for Yersinia microorganisms. The compound displays a mechanism of action like many β lactam antibiotics through inhibition of cell wall synthesis by competitively inhibiting penicillin binding protein (PBP) crosslinking of peptidoglycan resulting in inhibition of the final transpeptidation step. Through the inability for Cefsulodin sodium salt hydrate to inhibit cefsulodin-resistant mutants of Pseudomonas aeruginosa PAO4089 growth displayed that Cefsulodin sodium salt hydrate may compete with PBP3 in addition to PBP1A and PBP1B.
Verwenden
A β lactam antibiotic.
Verwenden
Cefsulodin is a third generation cephalosporin (C258750) antibiotic designed specifically for Pseudomonas Aeruginosa.
Verwenden
betaadrenergic blocker
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.
Trademarks
Cefomonil (TAP）.
Therapeutic Function
Antibiotic
Biologische Aktivität
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].
Einzelnachweise
[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.

cefsulodin sodium salt Upstream-Materialien And Downstream Produkte

[6R-[6α,7β(R*)]]-Hydrogen-4-carbamoyl-1-[[2-carboxylato-8-oxo-7-(phenylsulfonatoacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium, Mononatriumsalz Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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