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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H25N8O11S2.Na
Molecular Weight 712.643
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of Ceftobiprole Medocaril Sodium

SMILES

[Na+].CC1=C(COC(=O)N2CC[C@H](C2)N3CC\C(=C/C4=C(N5[C@H](SC4)[C@H](NC(=O)C(=N/O)\C6=NSC(N)=N6)C5=O)C([O-])=O)C3=O)OC(=O)O1

InChI

InChIKey=MFAWUGGPPMTWPU-LCJFHXTKSA-M
InChI=1S/C26H26N8O11S2.Na/c1-10-14(45-26(41)44-10)8-43-25(40)32-4-3-13(7-32)33-5-2-11(20(33)36)6-12-9-46-22-16(21(37)34(22)17(12)23(38)39)28-19(35)15(30-42)18-29-24(27)47-31-18;/h6,13,16,22,42H,2-5,7-9H2,1H3,(H,28,35)(H,38,39)(H2,27,29,31);/q;+1/p-1/b11-6+,30-15-;/t13-,16-,22-;/m1./s1

HIDE SMILES / InChI

Description

Ceftobiprole is a fifth-generation cephalosporin antibiotic. It was discovered by Basilea Pharmaceutica and was developed by Johnson & Johnson Pharmaceutical Research and Development. The drug is demonstrates activity against clinically important gram-positive pathogens, including methicillin-resistant Staphylococcus aureus, penicilliin-resistant Staphylococcus pneumoniae, and Enterococcus faecalis. The drug also has demonstrated activity against gram-negative bacteria including Citrobacter spp., Escherichia coli, Enterobacter spp., Klebsiella spp., Serratia marcescens, and Pseudomonas aeruginosa. The drug has gained regulatory authorization from European states for the treatment of hospital-acquired pneumonia (HAP, excluding ventilator-associated pneumonia, VAP) and community-acquired pneumonia (CAP).

Approval Year

2024
711
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Inhibitor
8504
PubMed

PubMed

TitleDatePubMed
Binding of ceftobiprole and comparators to the penicillin-binding proteins of Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pneumoniae.
2007 Jul
Non-susceptibility trends among staphylococci from bacteraemias in the UK and Ireland, 2001-06.
2008 Nov
In vivo pharmacodynamics of ceftobiprole against multiple bacterial pathogens in murine thigh and lung infection models.
2008 Oct
Prevalence of antimicrobial-resistant pathogens in Canadian hospitals: results of the Canadian Ward Surveillance Study (CANWARD 2008).
2010 Nov
Ceftobiprole activity against over 60,000 clinical bacterial pathogens isolated in Europe, Turkey, and Israel from 2005 to 2010.
2014 Jul
Patents

Patents

20040127703
3
WO2009051626A1
3
WO2010136423A1
3
Name Type Language
CEFTOBIPROLE MEDOCARIL
DASH   EMA EPAR   MART.   USAN  
Preferred Name English
Ceftobiprole Medocaril Sodium
WHO-DD  
USAN  
Official Name English
Ceftobiprole medocaril sodium [WHO-DD]
Common Name English
BAL5788
Code English
RO-65-5788
Code English
CEFTOBIPROLE MEDOCARIL [MART.]
Common Name English
CEFTOBIPROLE MEDOCARIL SODIUM SALT
MI  
Common Name English
ZEVTERA
Brand Name English
CEFTOBIPROLE MEDOCARIL SODIUM [USAN]
Common Name English
CEFTOBIPROLE MEDOCARIL SODIUM SALT [MI]
Common Name English
RO 65-5788
Code English
BAL-5788
Code English
BAL5788-001
Code English
BAL-5788-001
Code English
CEFTOBIPROLE MEDOCARIL [EMA EPAR]
Common Name English
RO-655788
Code English
Classification Tree Code System Code
WHO-ATC J01DI01
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
WHO-VATC QJ01DI01
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
NCI_THESAURUS C357
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
EMA ASSESSMENT REPORTS ZEFTERA (REFUSED SOFT TISSUE INFECTIONS)
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
Code System Code Type Description
DRUG BANK
DB14733
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
EVMPD
SUB130376
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
USAN
SS-13
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
CAS
252188-71-9
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
SMS_ID
100000156073
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
EPA CompTox
DTXSID601021562
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
FDA UNII
N99027V28J
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
DRUG CENTRAL
4402
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
ChEMBL
CHEMBL1652606
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
MERCK INDEX
m3223
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C70597
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
PUBCHEM
135413543
Created by admin on Mon Mar 31 18:05:36 GMT 2025 , Edited by admin on Mon Mar 31 18:05:36 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of CEFTOBIPROLE
NIH
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