Ceftaroline fosamil

• CAT Number: I011841
• CAS Number: 866021-48-9
• Molecular Formula: C22 H22 N8 O8 P S4 . C2 H3 O2 . H2 O
• Molecular Weight: 762.8
• Purity: ≥95%
• Storage: RT
• Related CAS: 400827-55-6
• IUPAC Name: acetic acid;(6R,7R)-7-[[(2Z)-2-ethoxyimino-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[[4-(1-methylpyridin-1-ium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrate
• InChI: InChI=1S/C22H21N8O8PS4.C2H4O2.H2O/c1-3-38-26-13(16-25-21(43-28-16)27-39(35,36)37)17(31)24-14-18(32)30-15(20(33)34)12(9-40-19(14)30)42-22-23-11(8-41-22)10-4-6-29(2)7-5-10;1-2(3)4;/h4-8,14,19H,3,9H2,1-2H3,(H4-,24,25,27,28,31,33,34,35,36,37);1H3,(H,3,4);1H2/b26-13-;;/t14-,19-;;/m1../s1
• InChIKey: KRWPPVCZNGQQHZ-IINIBMQSSA-N
• SMILES: O.CCON=C(/C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)Sc3nc(cs3)c4cc[n+](C)cc4)c5nsc(NP(=O)(O)O)n5.CC(=O)[O-]

Ceftaroline fosamil (CAT: I011841) is a prodrug of ceftaroline, which is a broad-spectrum cephalosporin antibiotic. Ceftaroline fosamil is administered intravenously and rapidly converted to its active form, ceftaroline, in the body. Ceftaroline exerts its antibacterial activity by inhibiting bacterial cell wall synthesis through binding to penicillin-binding proteins (PBPs). It exhibits potent activity against both Gram-positive and Gram-negative bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and Streptococcus pneumoniae. Ceftaroline fosamil is approved for the treatment of acute bacterial skin and skin structure infections (ABSSSI) and community-acquired bacterial pneumonia (CABP). It represents an important therapeutic option in the management of these infections, especially when caused by drug-resistant bacteria.

Reference

1: Taboada M, Melnick D, Iaconis JP, Sun F, Zhong NS, File TM, Llorens L, Friedland HD, Wilson D. Ceftaroline fosamil versus ceftriaxone for the treatment of community-acquired pneumonia: individual patient data meta-analysis of randomized controlled trials. J Antimicrob Chemother. 2016 Apr;71(4):862-70. doi: 10.1093/jac/dkv415. Epub 2015 Dec 24. Review. Erratum in: J Antimicrob Chemother. 2016 Jun;71(6):1748-9. PubMed PMID: 26702925.
2: Casapao AM, Steed ME, Levine DP, Rybak MJ. Ceftaroline fosamil for community-acquired bacterial pneumonia and acute bacterial skin and skin structure infection. Expert Opin Pharmacother. 2012 Jun;13(8):1177-86. doi: 10.1517/14656566.2012.685718. Review. PubMed PMID: 22594846.
3: Critchley IA, Eckburg PB, Jandourek A, Biek D, Friedland HD, Thye DA. Review of ceftaroline fosamil microbiology: integrated FOCUS studies. J Antimicrob Chemother. 2011 Apr;66 Suppl 3:iii45-51. doi: 10.1093/jac/dkr098. Review. PubMed PMID: 21482569.
4: Biek D, Critchley IA, Riccobene TA, Thye DA. Ceftaroline fosamil: a novel broad-spectrum cephalosporin with expanded anti-Gram-positive activity. J Antimicrob Chemother. 2010 Nov;65 Suppl 4:iv9-16. doi: 10.1093/jac/dkq251. Review. PubMed PMID: 21115457.