CHEBI:3480 - cefamandole

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ChEBI Name cefamandole
ChEBI ID CHEBI:3480
Definition A cephalosporin compound having (R)-mandelamido and N-methylthiotetrazole side-groups.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H18N6O5S2
Net Charge 0
Average Mass 462.50300
Monoisotopic Mass 462.078
InChI InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
InChIKey OLVCFLKTBJRLHI-AXAPSJFSSA-N
SMILES [H][C@]12SCC(CSc3nnnn3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)c1ccccc1)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 )
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ChEBI Ontology
Outgoing cefamandole (CHEBI:3480) has role antibacterial drug (CHEBI:36047)
cefamandole (CHEBI:3480) is a cephalosporin (CHEBI:23066)
cefamandole (CHEBI:3480) is a semisynthetic derivative (CHEBI:72588)
cefamandole (CHEBI:3480) is conjugate acid of cefamandole(1−) (CHEBI:53652)
Incoming O-formylcefamandole (CHEBI:53654) has functional parent cefamandole (CHEBI:3480)
cefamandole(1−) (CHEBI:53652) is conjugate base of cefamandole (CHEBI:3480)
IUPAC Name
7β-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic acid
INNs Sources
cefamandol ChemIDplus
cefamandole KEGG DRUG
céfamandole WHO MedNet
cefamandolum ChemIDplus
Synonyms Sources
(6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid ChemIDplus
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid IUPAC
Cefadole ChemIDplus
Cephadole ChemIDplus
Cephamandole ChemIDplus
L-Cefamandole ChemIDplus
Manual Xrefs Databases
527 DrugCentral
C06879 KEGG COMPOUND
Cefamandole Wikipedia
D02344 KEGG DRUG
DB01326 DrugBank
DE2018600 Patent
DE2312997 Patent
US3641021 Patent
US3840531 Patent
View more database links
Registry Numbers Types Sources
34444-01-4 CAS Registry Number KEGG COMPOUND
34444-01-4 CAS Registry Number ChemIDplus
34444-01-4 CAS Registry Number KEGG DRUG
34444-01-4 CAS Registry Number DrugBank
5406309 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
12569987 PubMed citation Europe PMC
12833570 PubMed citation Europe PMC
15828189 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
Last Modified
13 February 2018