Ceftobiprole Medocaril

Title: Ceftobiprole Medocaril
CAS Registry Number: 376653-43-9
CAS Name: (6R,7R)-7-[[(2Z)-(5-Amino-1,2,4-thiadiazol-3-yl)(hydroxyimino)acetyl]amino]-3-[(E)-[(3¢R)-1¢-[[(5-methyl-2-oxo-1,3-dioxol-4-yl)methoxy]carbonyl]-2-oxo[1,3¢-bipyrrolidin]-3-ylidene]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular Formula: C26H26N8O11S2
Molecular Weight: 690.66
Percent Composition: C 45.21%, H 3.79%, N 16.22%, O 25.48%, S 9.29%
Literature References: Fourth generation cephalosporin antibiotic prodrug; rapidly cleaved in plasma to the active metabolite, ceftobiprole. Prepn: P. Hebeisen et al., WO 9965920; eidem, US 6232306 (1999, 2001 both to Hoffmann-La Roche). In vitro and in vivo activity against methicillin-resistant Staphylococcus aureus (MRSA): idem et al., Antimicrob. Agents Chemother. 45, 825 (2001). Comparative antibacterial spectrum in vitro: R. N. Jones et al., J. Antimicrob. Chemother. 50, 915 (2002). In vivo activity in experimental pneumococcal pneumonia: E. Azoulay-Dupuis et al., Antimicrob. Agents Chemother. 48, 1105 (2004). Clinical pharmacokinetics and safety: A. Schmitt-Hoffmann et al., ibid. 48, 2576 (2004).
Derivative Type: Sodium salt
CAS Registry Number: 252188-71-9
Manufacturers' Codes: BAL-5788; Ro-65-5788
Molecular Formula: C26H25N8NaO11S2
Molecular Weight: 712.64
Percent Composition: C 43.82%, H 3.54%, N 15.72%, Na 3.23%, O 24.70%, S 9.00%
Properties: Sol in water.
Derivative Type: Ceftobiprole
CAS Registry Number: 209467-52-7
CAS Name: (6R,7R)-7-[[(2Z)-(5-Amino-1,2,4-thiadiazol-3-yl)(hydroxyimino)acetyl]amino]-8-oxo-3[(E)-[(3¢R)-2-oxo[1,3¢-bipyrrolidin]-3-ylidene]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Manufacturers' Codes: BAL-9141; Ro-63-9141
Molecular Formula: C20H22N8O6S2
Molecular Weight: 534.57
Percent Composition: C 44.94%, H 4.15%, N 20.96%, O 17.96%, S 12.00%
Literature References: Prepn: P. Angehrn et al., EP 849269; eidem, US 5981519 (1997, 1999 both to Hoffmann-La Roche).
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
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