Ceftobiprole

Structural formula
General
Non-proprietary name	Ceftobiprole
other names	(6 R , 7 R ) -7 - [(2 Z ) -2- (5-amino-1,2,4-thiadiazol-3-yl) -2- (hydroxyimino) acetamido] -8-oxo-3- [( E ) - {(3 ' R ) -2-oxo- [1,3'-bipyrrolidin] -3-ylidene} methyl] -5-thia-1-azabicyclo [4.2.0] oct-2-en- 2-carboxylic acid ( IUPAC )
Molecular formula	C 20 H 22 N 8 O 8 S 2
External identifiers / databases
CAS number 209467-52-7 (ceftobiprole) 252188-71-9 (Ceftobiprole Medocaril Sodium) EC number 606-675-3 ECHA InfoCard 100.129.666 PubChem 135413542 ChemSpider 23350302 DrugBank DB04918 Wikidata Q5057301
Drug information
ATC code	J01 DI01
Drug class	β-lactam antibiotic 5th generation cephalosporin
Mechanism of action	Inhibition of cell wall synthesis
properties
Molar mass	534.57 g · mol -1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ceftobiprole [ brand names : Zevtera (D, A, CH) and Mabelio ( BE , F ); Marketing authorization holder: Basilea Pharmaceutica ] is an antibiotic from the group of cephalosporins . The bactericidal effect is, as with other β-lactam antibiotics and, by inhibiting bacterial cell wall synthesis. As a 5th generation cephalosporin, ceftobiprole is also effective against MRSA in contrast to most other β-lactam antibiotics .

In the gram-negative spectrum, ceftobiprole shows good in-vitro activity against Haemophilus influenzae (including ampicillin-resistant strains), Pseudomonas aeruginosa and Enterobacterales such as Escherichia coli , Klebsiella pneumoniae and Proteus mirabilis . As usual for cephalosporins, ceftobiprole is not effective against pathogens that have an extended spectrum β-lactamase .

Ceftobiprole is approved for the treatment of nosocomial and community-acquired pneumonia (with the exception of ventilator-associated pneumonia) in adults. Ceftobiprole can only be administered parenterally . Studies also suggest a benefit in the treatment of complex skin and soft tissue infections; However, an EU application for approval from Janssen-Cilag for this indication failed in 2010 because the approval studies at some test centers had not been carried out in accordance with the guidelines of good clinical practice (GCP).

Structure of the prodrug ceftobiprole medocaril

The sodium salt of ceftobiprole medocaril is used medicinally due to its better water solubility. Ceftobiprole medocaril is a prodrug from which the active ceftobiprole is formed in vivo by hydrolysis .

Individual evidence

1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
2. ↑ David J. Farrell, Robert K. Flamm, Helio S. Sader, Ronald N. Jones: Ceftobiprole activity against over 60,000 clinical bacterial pathogens isolated in Europe, Turkey, and Israel from 2005 to 2010 . In: Antimicrobial Agents and Chemotherapy . 58, No. 7, July 1, 2014, pp. 3882-3888. doi : 10.1128 / AAC.02465-14 . PMID 24777091 . PMC 4068590 (free full text).
3. ↑ Avoxa ?? Mediengruppe Deutscher Apotheker GmbH: Pharmaceutical newspaper online - Drugs: Ceftobiprole (Zevtera® / 2014). In: www.pharmazeutische-zeitung.de. Retrieved December 22, 2016 . 
4. ↑ Denial of the marketing authorization for Zeftera (ceftobiprole) , EMA Questions and Answers of June 24, 2010, accessed on August 12, 2017.
5. ↑ External identifiers or database links for ceftobiprole medocaril sodium : CAS number: 252188-71-9, EC number: 607-653-6, ECHA InfoCard: 100.129.109 , ChemSpider : 30791463 , Wikidata : Q27284724 .

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