EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:140407 - ceftobiprole

ChEBI IDCHEBI:140407
ChEBI Nameceftobiprole
Stars
DefinitionA fifth-generation cephalosporin antibiotic having (E)-[(3'R)-2-oxo[1,3'-bipyrrolidin]-3-ylidene]methyl and [(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(hydroxyimino)acetyl]amino side groups located at positions 3 and 7 respectively; developed for the treatment of hospital-acquired pneumonia (HAP, excluding ventilator-associated pneumonia, VAP) and community-acquired pneumonia (CAP).
Last Modified12 March 2018
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC20H22N8O6S2
Net Charge0
Average Mass534.580
Monoisotopic Mass534.11037
SMILES[H][C@@]1(N2CC/C(=C\C3=C(C(=O)O)N4C(=O)[C@@]([H])(NC(=O)/C(=N\O)c5nsc(N)n5)[C@@]4([H])SC3)C2=O)CCNC1
InChIInChI=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
InChIKeyVOAZJEPQLGBXGO-SDAWRPRTSA-N
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
drug allergen  Any drug which causes the onset of an allergic reaction.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
drug allergen  Any drug which causes the onset of an allergic reaction.
ChEBI Ontology
Outgoing Relation(s)
ceftobiprole (CHEBI:140407) has role antimicrobial agent (CHEBI:33281)
ceftobiprole (CHEBI:140407) is a cephalosporin (CHEBI:23066)
ceftobiprole (CHEBI:140407) is a thiadiazoles (CHEBI:38099)
IUPAC Name 
7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(hydroxyimino)acetyl]amino}-3-{(E)-[(3'R)-2-oxo[1,3'-bipyrrolidin]-3-ylidene]methyl}-3,4-didehydrocepham-4-carboxylic acid
INNs  Source
ceftobiproleChemIDplus
ceftobiprolWHO MedNet
ceftobiprolumWHO MedNet
ceftobiproleWHO MedNet
Synonym  Source
(6R,7R)-7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(hydroxyimino)acetyl]amino}-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 acidIUPAC
Manual XrefsDatabases
D08885KEGG DRUG
Registry NumbersSources
Reaxys:9105776Reaxys
CAS:209467-52-7ChemIDplus
Citations