CHEBI:3488 - cefluprenam

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ChEBI Name cefluprenam
ChEBI ID CHEBI:3488
Definition A fourth-generation cephalosporin antibiotic having (1E)-3-[(2-amino-2-oxoethyl)(ethyl)methylazaniumyl]prop-1-en-1-yl and {(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[(fluoromethoxy)imino]acetyl}amino side groups located at positions 3 and 7 respectively.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H25FN8O6S2
Net Charge 0
Average Mass 556.594
Monoisotopic Mass 556.13225
InChI InChI=1S/C20H25FN8O6S2/c1-3-29(2,7-11(22)30)6-4-5-10-8-36-18-13(17(32)28(18)14(10)19(33)34)24-16(31)12(26-35-9-21)15-25-20(23)37-27-15/h4-5,13,18H,3,6-9H2,1-2H3,(H5-,22,23,24,25,27,30,31,33,34)/b5-4+,26-12-/t13-,18-,29?/m1/s1
InChIKey XAKKNLNAJBNLPC-MAYKBZFQSA-N
SMILES [C@]12(N(C(=C(CS1)/C=C/C[N+](CC(N)=O)(CC)C)C(=O)[O-])C([C@H]2NC(=O)/C(/C3=NSC(=N3)N)=N\OCF)=O)[H]
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 cefluprenam (CHEBI:3488) has role antimicrobial agent (CHEBI:33281)
cefluprenam (CHEBI:3488) is a cephalosporin (CHEBI:23066)
cefluprenam (CHEBI:3488) is a thiadiazoles (CHEBI:38099)
IUPAC Name
7-({(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[(fluoromethoxy)imino]acetyl}amino)-3-[(1E)-3-[(2-amino-2-oxoethyl)(ethyl)methylazaniumyl]prop-1-en-1-yl]-3,4-didehydrocepham-4-carboxylate
INNs Sources
cefluprenam ChemIDplus
céfluprénam WHO MedNet
cefluprenam WHO MedNet
cefluprenamum WHO MedNet
Synonyms Sources
(6R,7R)-3-{(1E)-3-[(2-amino-2-oxoethyl)(ethyl)methylazaniumyl]prop-1-en-1-yl}-7-({(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[(fluoromethoxy)imino]acetyl}amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate IUPAC
Antibiotic E 1077 ChEBI
Manual Xrefs Databases
Cefluprenam Wikipedia
D01054 KEGG DRUG
US5994340 Patent
View more database links
Registry Number Type Source
116853-25-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
18611779 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
9311195 PubMed citation Europe PMC
Last Modified
12 March 2018