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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H26N8O11S2
Molecular Weight 690.662
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CEFTOBIPROLE MEDOCARIL FREE ACID

SMILES

[H][C@]12SCC(\C=C3/CCN([C@@H]4CCN(C4)C(=O)OCC5=C(C)OC(=O)O5)C3=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C6=NSC(N)=N6)C(O)=O

InChI

InChIKey=HFTSMHTWUFCYMJ-YIOMYIDASA-N
InChI=1S/C26H26N8O11S2/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)/b11-6+,30-15-/t13-,16-,22-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H26N8O11S2
Molecular Weight 690.662
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

Targets

PubMed

PubMed

TitleDatePubMed
Activity of ceftobiprole against community-associated methicillin-resistant Staphylococcus aureus isolates recently recovered from US military trainees.
2007 Dec
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
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:49:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:39 GMT 2023
Record UNII
YXV28V1B07
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFTOBIPROLE MEDOCARIL FREE ACID
Common Name English
CEFTOBIPROLE MEDOCARIL [MI]
Common Name English
Ceftobiprole medocaril [WHO-DD]
Common Name English
ceftobiprole medocaril [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC J01DI01
Created by admin on Fri Dec 15 15:49:39 GMT 2023 , Edited by admin on Fri Dec 15 15:49:39 GMT 2023
Code System Code Type Description
SMS_ID
100000091689
Created by admin on Fri Dec 15 15:49:39 GMT 2023 , Edited by admin on Fri Dec 15 15:49:39 GMT 2023
PRIMARY
INN
8532
Created by admin on Fri Dec 15 15:49:39 GMT 2023 , Edited by admin on Fri Dec 15 15:49:39 GMT 2023
PRIMARY
MERCK INDEX
m3223
Created by admin on Fri Dec 15 15:49:39 GMT 2023 , Edited by admin on Fri Dec 15 15:49:39 GMT 2023
PRIMARY Merck Index
FDA UNII
YXV28V1B07
Created by admin on Fri Dec 15 15:49:39 GMT 2023 , Edited by admin on Fri Dec 15 15:49:39 GMT 2023
PRIMARY
MESH
C505439
Created by admin on Fri Dec 15 15:49:39 GMT 2023 , Edited by admin on Fri Dec 15 15:49:39 GMT 2023
PRIMARY
EVMPD
SUB25721
Created by admin on Fri Dec 15 15:49:39 GMT 2023 , Edited by admin on Fri Dec 15 15:49:39 GMT 2023
PRIMARY
PUBCHEM
135413544
Created by admin on Fri Dec 15 15:49:39 GMT 2023 , Edited by admin on Fri Dec 15 15:49:39 GMT 2023
PRIMARY
NCI_THESAURUS
C170536
Created by admin on Fri Dec 15 15:49:39 GMT 2023 , Edited by admin on Fri Dec 15 15:49:39 GMT 2023
PRIMARY
CAS
376653-43-9
Created by admin on Fri Dec 15 15:49:39 GMT 2023 , Edited by admin on Fri Dec 15 15:49:39 GMT 2023
PRIMARY
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