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

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
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
Activity of ceftobiprole against community-associated methicillin-resistant Staphylococcus aureus isolates recently recovered from US military trainees.	2007 Dec	17911001
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

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:49:40 GMT 2023` Edited by `admin` on `Fri Dec 15 15:49:40 GMT 2023`
Record UNII	5T97333YZK
Record Status	`Validated (UNII)`
Record Version

Download

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