CHEBI:140407 - ceftobiprole

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ChEBI Name ceftobiprole
ChEBI ID CHEBI:140407
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H22N8O6S2
Net Charge 0
Average Mass 534.572
Monoisotopic Mass 534.11037
InChI 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
InChIKey VOAZJEPQLGBXGO-SDAWRPRTSA-N
SMILES C=1(N2[C@](SCC1/C=C/3\CCN(C3=O)[C@]4(CNCC4)[H])([C@@](C2=O)(NC(/C(/C5=NSC(=N5)N)=N\O)=O)[H])[H])C(O)=O
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
Application(s): drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
ceftobiprol WHO MedNet
ceftobiprole WHO MedNet
ceftobiprole ChemIDplus
ceftobiprolum WHO 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 acid IUPAC
Manual Xref Database
D08885 KEGG DRUG
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Registry Numbers Types Sources
209467-52-7 CAS Registry Number ChemIDplus
9105776 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
25753637 PubMed citation Europe PMC
26316697 PubMed citation Europe PMC
26443816 PubMed citation Europe PMC
28264613 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
29395713 PubMed citation Europe PMC
29452992 PubMed citation Europe PMC
PMC5631058 PubMed Central citation Europe PMC
Last Modified
12 March 2018