CEFTOBIPROLE

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 Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19750059 | https://www.cnbc.com/2014/07/21/globe-newswire-basilea-to-launch-zevterarmabelior-ceftobiprole-medocaril-in-europe-through-a-commercial-services-provider.html

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
Staphylococcus aureus 67 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25117196	Inhibitor 8297
Penicillin-binding protein 2a 17 Target ID: CHEMBL3512 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16922591	Inhibitor 8297

PubMed

Title	Date	PubMed
Binding of ceftobiprole and comparators to the penicillin-binding proteins of Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pneumoniae.	2007 Jul	17470659
Clinical profile of ceftobiprole, a novel beta-lactam antibiotic.	2007 Jun	17488373
Activity of ceftobiprole compared with those of other agents against Staphylococcus aureus strains with different resistotypes by time-kill analysis.	2008 Feb	17997257
In vivo pharmacodynamics of ceftobiprole against multiple bacterial pathogens in murine thigh and lung infection models.	2008 Oct	18676887
Prevalence of antimicrobial-resistant pathogens in Canadian hospitals: results of the Canadian Ward Surveillance Study (CANWARD 2008).	2010 Nov	20805395
Ceftobiprole activity against over 60,000 clinical bacterial pathogens isolated in Europe, Turkey, and Israel from 2005 to 2010.	2014 Jul	24777091

Patents

Name

Type

Language

CEFTOBIPROLE

Official Name

English

BAL-9141-000

Code

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