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
SMILES
[H][C@]12SCC(\C=C3/CCN([C@@H]4CCNC4)C3=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C5=NSC(N)=N5)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
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 |
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25117196 |
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Target ID: CHEMBL3512 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16922591 |
PubMed
Title | Date | PubMed |
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Activity of ceftobiprole against community-associated methicillin-resistant Staphylococcus aureus isolates recently recovered from US military trainees. | 2007 Dec |
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Clinical profile of ceftobiprole, a novel beta-lactam antibiotic. | 2007 Jun |
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Activity of ceftobiprole compared with those of other agents against Staphylococcus aureus strains with different resistotypes by time-kill analysis. | 2008 Feb |
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Results of a double-blind, randomized trial of ceftobiprole treatment of complicated skin and skin structure infections caused by gram-positive bacteria. | 2008 Jan |
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Non-susceptibility trends among staphylococci from bacteraemias in the UK and Ireland, 2001-06. | 2008 Nov |
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In vivo pharmacodynamics of ceftobiprole against multiple bacterial pathogens in murine thigh and lung infection models. | 2008 Oct |
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Prevalence of antimicrobial-resistant pathogens in Canadian hospitals: results of the Canadian Ward Surveillance Study (CANWARD 2008). | 2010 Nov |
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Ceftobiprole activity against over 60,000 clinical bacterial pathogens isolated in Europe, Turkey, and Israel from 2005 to 2010. | 2014 Jul |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:49:40 GMT 2023
by
admin
on
Fri Dec 15 15:49:40 GMT 2023
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Record UNII |
5T97333YZK
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C357
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SS-12
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209467-52-7
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135413542
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m3223
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100000091899
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5T97333YZK
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Ceftobiprole
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C443755
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SUB25723
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140407
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CHEMBL520642
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DTXSID40870229
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8531
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C65306
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DB04918
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Related Record | Type | Details | ||
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TARGET ORGANISM->INHIBITOR |
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TARGET ORGANISM->INHIBITOR |
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
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