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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H22N8O6S2
Molecular Weight 534.569
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CEFTOBIPROLE

SMILES

NC1=NC(=NS1)C(=N\O)\C(=O)N[C@H]2[C@H]3SCC(\C=C4/CCN([C@@H]5CCNC5)C4=O)=C(N3C2=O)C(O)=O

InChI

InChIKey=VOAZJEPQLGBXGO-SDAWRPRTSA-N
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

HIDE SMILES / InChI
Molecular Formula C20H22N8O6S2
Molecular Weight 534.569
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 2
Optical Activity UNSPECIFIED

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
Clinical profile of ceftobiprole, a novel beta-lactam antibiotic.
2007 Jun
Results of a double-blind, randomized trial of ceftobiprole treatment of complicated skin and skin structure infections caused by gram-positive bacteria.
2008 Jan
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:10:06 GMT 2025
Edited
by admin
on Mon Mar 31 18:10:06 GMT 2025
Record UNII
5T97333YZK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BAL-9141-000
Preferred Name English
CEFTOBIPROLE
INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
BAL9141-000
Code English
RO-639141
Code English
RO 63-9141
Code English
(6R,7R)-7-((2Z)-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-ENE-2-CARBOXYLIC ACID
Systematic Name English
CEFTOBIPROLE [USAN]
Common Name English
Ceftobiprole [WHO-DD]
Common Name English
CEFTOBIPROLE [MI]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2Z)-(5-AMINO-1,2,4-THIADIAZOL-3-YL)(HYDROXYIMINO)ACETYL)AMINO)-8-OXO-3-((E)-((3'R)-2-
Common Name English
RO-63-9141
Code English
BAL-9141000
Code English
ceftobiprole [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
Code System Code Type Description
USAN
SS-12
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
CAS
209467-52-7
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
PUBCHEM
135413542
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
MERCK INDEX
m3223
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY Merck Index
SMS_ID
100000091899
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
FDA UNII
5T97333YZK
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
WIKIPEDIA
Ceftobiprole
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
MESH
C443755
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
EVMPD
SUB25723
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
CHEBI
140407
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
ChEMBL
CHEMBL520642
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
EPA CompTox
DTXSID40870229
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
INN
8531
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
NCI_THESAURUS
C65306
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
DRUG BANK
DB04918
Created by admin on Mon Mar 31 18:10:06 GMT 2025 , Edited by admin on Mon Mar 31 18:10:06 GMT 2025
PRIMARY
Related Record Type Details
STREPTOCOCCUS PNEUMONIAE
TARGET ORGANISM->INHIBITOR
METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS
TARGET ORGANISM->INHIBITOR
Related Record Type Details
Structure of CEFTOBIPROLE MEDOCARIL FREE ACID
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of CEFTOBIPROLE
ACTIVE MOIETY
NIH
NCATS
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