Ceftobiprole

For research use only. Not for therapeutic Use.

  • CAT Number: I005926
  • CAS Number: 209467-52-7
  • Molecular Formula: C20H22N8O6S2
  • Molecular Weight: 534.57
  • Purity: ≥95%
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Ceftobiprole (Cat No.:I005926) is a broad-spectrum cephalosporin antibiotic used for the treatment of bacterial infections. It belongs to the fifth generation of cephalosporins and exhibits activity against a wide range of Gram-positive and Gram-negative bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and penicillin-resistant Streptococcus pneumoniae. Ceftobiprole works by inhibiting bacterial cell wall synthesis through binding to penicillin-binding proteins (PBPs). This mechanism of action disrupts the integrity of the bacterial cell wall, leading to cell death. Ceftobiprole has been approved for the treatment of complicated skin and skin structure infections (cSSSI) and community-acquired pneumonia (CAP).


Catalog Number I005926
CAS Number 209467-52-7
Synonyms

Ceftobiprole; BAL 9141; AC1OCFF8; Zeftera; UNII-5T97333YZK; BAL-9141; BAL9141.;(6R,7R)-7-((Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-((E)-((R)-2-oxo-[1,3/’-bipyrrolidin]-3-ylidene)methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-

Molecular Formula C20H22N8O6S2
Purity ≥95%
Solubility Soluble in DMSO, not in water
Storage 0 - 4°C for short term ,or -20 °C for long term
Overview of Clinical Research

Originator: Basilea Pharmaceutica; Roche<br />
Class: Cephalosporins; Skin disorder therapies; Small molecules<br />
Mechanism of Action: Cell wall inhibitors; Peptidyltransferase inhibitors<br />
Orphan Drug Status: No<br />
New Molecular Entity: Yes

IUPAC Name (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(E)-[2-oxo-1-[(3R)-pyrrolidin-3-yl]pyrrolidin-3-ylidene]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChI InChI=1S/C20H22N8O6S2/c21-20-24-14(26-36-20)11(25-34)15(29)23-12-17(31)28-13(19(32)33)9(7-35-18(12)28)5-8-2-4-27(16(8)30)10-1-3-22-6-10/h5,10,12,18,22,34H,1-4,6-7H2,(H,23,29)(H,32,33)(H2,21,24,26)/b8-5+,25-11-/t10-,12-,18-/m1/s1
InChIKey VOAZJEPQLGBXGO-SDAWRPRTSA-N
SMILES C1CNCC1N2CCC(=CC3=C(N4C(C(C4=O)NC(=O)C(=NO)C5=NSC(=N5)N)SC3)C(=O)O)C2=O
Reference

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1:Corrigendum to /Rates of susceptibility of carbapenems, ceftobiprole, and colistin against clinically important bacteria collected from intensive care units in 2007: Results from the Surveillance of Multicenter Antimicrobial Resistance in Taiwan (SMART)/ [J Microbiol Immunol Infect 49 (2016) 969-976]. Jean SS, Lee WS, Yu KW, Liao CH, Hsu CW, Chang FY, Ko WC, Chen RJ, Wu JJ, Chen YH, Chen YS, Liu JW, Lu MC, Lam C, Liu CY, Hsueh PR.J Microbiol Immunol Infect. 2017 Mar 16. pii: S1684-1182(17)30001-4. doi: 10.1016/j.jmii.2017.01.001. [Epub ahead of print] No abstract available. PMID: 28325540 Free Article<br />
2:Pharmacokinetic drug evaluation of ceftobiprole for the treatment of MRSA. Horn KS, Danziger LH, Rodvold KA, Glowacki RC.Expert Opin Drug Metab Toxicol. 2017 Apr;13(4):463-472. doi: 10.1080/17425255.2017.1303481. Epub 2017 Mar 17. Review. PMID: 28264613<br />
3:In vitro activity of ceftobiprole on 440 Staphylococcus aureus strains isolated from bronchopulmonary infections. Hodille E, Delouere L, Bouveyron C, Meugnier H, Bes M, Tristan A, Laurent F, Vandenesch F, Lina G, Dumitrescu O.Med Mal Infect. 2017 Mar;47(2):152-157. doi: 10.1016/j.medmal.2016.10.004. Epub 2016 Nov 14. PMID: 27856079<br />
4:Ceftobiprole medocaril (BAL-5788) for the treatment of complicated skin infections. Deitchman A, de Jong D, Barbour A, Derendorf H.Expert Rev Anti Infect Ther. 2016 Oct 2. [Epub ahead of print] PMID: 27690689<br />
5:Pharmacokinetics and Dosing of Ceftobiprole Medocaril for the Treatment of Hospital- and Community-Acquired Pneumonia in Different Patient Populations. Torres A, Mouton JW, Pea F.Clin Pharmacokinet. 2016 Dec;55(12):1507-1520. Review. PMID: 27272266 Free PMC Article<br />
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