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SML3102

Sigma-Aldrich

Ceftaroline fosamil acetate hydrate

≥98% (HPLC)

Synonym(s):

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

Empirical Formula (Hill Notation):
C22H22N8O8PS4 · C2H3O2 · xH2O
CAS Number:
400827-46-5
Molecular Weight:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Evaluation of the in vivo efficacy of intramuscularly administered ceftaroline fosamil, a novel cephalosporin, against a methicillin-resistant Staphylococcus aureus strain in a rabbit endocarditis model.
Cédric Jacqueline et al.
The Journal of antimicrobial chemotherapy, 65(10), 2264-2265 (2010-08-19)
D Andes et al.
Antimicrobial agents and chemotherapy, 50(4), 1376-1383 (2006-03-30)
PPI-0903 is a new cephalosporin with broad-spectrum activity, including beta-lactam-resistant Streptococcus pneumoniae and Staphylococcus aureus. We used the neutropenic murine thigh and lung infection models to examine the pharmacodynamic characteristics of PPI-0903. Serum drug levels following four fourfold-escalating single doses
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
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
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