U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Clinical profile of ceftobiprole, a novel beta-lactam antibiotic.
2007 Jun
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
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
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY