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SML3102

Sigma-Aldrich

Ceftaroline fosamil acetate hydrate

≥98% (HPLC)

Sinónimos:

4-(2-((6R,7R)-2-Carboxy-7-((Z)-2-(ethoxyimino)-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-ylthio)thiazol-4-yl)-1-methylpyridinium acetate, hydrate, Ceftaroline fosamil acetate hydrate, PPI 0903 hydrate, PPI-0903 hydrate, PPI0903 hydrate, TAK 599 hydrate, TAK-599 hydrate, TAK599 hydrate

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About This Item

Fórmula empírica (notación de Hill):
C22H22N8O8PS4 · C2H3O2 · xH2O
Número de CAS:
400827-46-5
Peso molecular:
744.74 (anhydrous basis)
MDL number:
MFCD29920090
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

C[N+]1=CC=C(C=C1)C2=CSC(SC(CS[C@@]3([C@@H]4NC(/C(C5=NSC(NP(O)(O)=O)=N5)=N\OCC)=O)[H])=C(N3C4=O)C(O)=O)=N2.CC([O-])=O

Biochem/physiol Actions

Ceftaroline fosamil (PPI-0903, TAK-599) is a N-phosphono type prodrug of ceftaroline (cephalosporin 2a, PPI-0903M, T-91825), a fifth-generation penicillin-binding protein (PBP)-targeting cephalosporin class beta-lactam (β-lactam) antibiotic with broad-spectrum activity against gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and extensively-resistant strains, such as vancomycin-intermediate S. aureus (VISA), heteroresistant VISA (hVISA), and vancomycin-resistant S. aureus (VRSA).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

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Christopher Duplessis et al.
Clinical medicine reviews in therapeutics, 3 (2011-07-26)
Microbial resistance has reached alarming levels, threatening to outpace the ability to counter with more potent antimicrobial agents. In particular, methicillin-resistant Staphylococcus aureus (MRSA) has become a leading cause of skin and soft-tissue infections and PVL-positive strains have been associated
Yuji Iizawa et al.
Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy, 10(3), 146-156 (2004-08-04)
TAK-599 is a water-soluble prodrug of a cephalosporin compound, T-91825. In vitro and in vivo antibacterial activities of T-91825 and TAK-599, respectively, were examined. T-91825 was active against both gram-positive and gram-negative bacteria, unlike vancomycin and linezolid, which are inactive
Cédric Jacqueline et al.
The Journal of antimicrobial chemotherapy, 66(4), 863-866 (2011-03-12)
The aim of this study was to compare the in vivo activities of the new antistaphylococcal drugs ceftaroline fosamil, daptomycin and tigecycline at projected human therapeutic doses against methicillin-susceptible Staphylococcus aureus (MSSA), methicillin-resistant S. aureus (MRSA) and glycopeptide-intermediate S. aureus
Cédric Jacqueline et al.
Antimicrobial agents and chemotherapy, 51(9), 3397-3400 (2007-06-27)
Using the rabbit endocarditis model, we compared the activity of a new broad-spectrum cephalosporin, ceftaroline, with those of linezolid and vancomycin against methicillin-resistant Staphylococcus aureus. After a 4-day treatment, ceftaroline exhibited superior bactericidal in vivo activity against resistant S. aureus
Tomoyasu Ishikawa et al.
Bioorganic & medicinal chemistry, 11(11), 2427-2437 (2003-05-09)
Crystalline 1 (TAK-599) is a novel N-phosphono prodrug of anti-methicillin-resistant Staphylococcus aureus (MRSA) cephalosporin 2a (T-91825) that has high affinity for penicillin-binding protein (PBP) 2' (IC(50); 0.90 microg/mL) and shows potent in vitro anti-MRSA activity (MIC against MRSA N133; 1.56
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