CHEBI:140116 - ceftiolene

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ChEBI Name ceftiolene
ChEBI ID CHEBI:140116
Definition A cephalosporin compound having (E)-2-{[5,6-dioxo-4-(2-oxoethyl)-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl]sulfanyl}ethenyl and [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side-groups; a third-generation cephalosporin antibiotic.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H18N8O8S3
Net Charge 0
Average Mass 594.590
Monoisotopic Mass 594.04097
InChI InChI=1S/C20H18N8O8S3/c1-36-26-10(9-7-39-19(21)22-9)13(30)23-11-15(32)28-12(18(34)35)8(6-38-17(11)28)2-5-37-20-25-24-14(31)16(33)27(20)3-4-29/h2,4-5,7,11,17H,3,6H2,1H3,(H2,21,22)(H,23,30)(H,24,31)(H,34,35)/b5-2+,26-10-/t11-,17-/m1/s1
InChIKey WJXAHFZIHLTPFR-JLRJEBFFSA-N
SMILES [H]C(=O)CN1C(=O)C(=O)NN=C1S\C=C\C1=C(N2C(=O)[C@@H](NC(=O)C(=N/OC)\C3=CSC(N)=N3)[C@@]2([H])SC1)C(O)=O
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ceftiolene (CHEBI:140116) has role antibacterial drug (CHEBI:36047)
ceftiolene (CHEBI:140116) is a cephalosporin (CHEBI:23066)
IUPAC Name
3-[(E)-2-{[5,6-dioxo-4-(2-oxoethyl)-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl]sulfanyl}ethenyl]-7β-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3,4-didehydrocepham-4-carboxyic acid
INNs Sources
ceftioléne WHO MedNet
ceftiolene WHO MedNet
ceftioleno WHO MedNet
ceftiolenum WHO MedNet
Synonyms Sources
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(E)-2-{[5,6-dioxo-4-(2-oxoethyl)-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl]sulfanyl}ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid IUPAC
42980RP ChEBI
Manual Xrefs Databases
5020599 ChemSpider
Ceftiolene Wikipedia
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Registry Number Type Source
77360-52-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
29017833 PubMed citation Europe PMC
3733516 PubMed citation Europe PMC
6394571 PubMed citation Europe PMC
6739141 PubMed citation Europe PMC
Last Modified
23 November 2020