CHEBI:3504 - cefpodoxime

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ChEBI Name cefpodoxime
ChEBI ID CHEBI:3504
Definition A third-generation cephalosporin antibiotic with methoxymethyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamino substituents at positions 3 and 7, respectively, of the cephem skeleton. Given by mouth as its proxetil ester prodrug, it is used to treat acute otitis media, pharyngitis, and sinusitis.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:606443
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Formula C15H17N5O6S2
Net Charge 0
Average Mass 427.45500
Monoisotopic Mass 427.06203
InChI InChI=1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1
InChIKey WYUSVOMTXWRGEK-HBWVYFAYSA-N
SMILES [H][C@]12SCC(COC)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\c1csc(N)n1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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 cefpodoxime (CHEBI:3504) has role antibacterial drug (CHEBI:36047)
cefpodoxime (CHEBI:3504) is a carboxylic acid (CHEBI:33575)
cefpodoxime (CHEBI:3504) is a cephalosporin (CHEBI:23066)
Incoming cefpodoxime proxetil (CHEBI:3505) has functional parent cefpodoxime (CHEBI:3504)
IUPAC Name
7β-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-3,4-didehydrocepham-4-carboxylic acid
INNs Sources
cefpodoxima ChemIDplus
cefpodoxime ChemIDplus
cefpodoximum ChemIDplus
Synonym Source
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid IUPAC
Manual Xrefs Databases
2968 VSDB
C08114 KEGG COMPOUND
Cefpodoxime Wikipedia
D07650 KEGG DRUG
DB01416 DrugBank
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Registry Numbers Types Sources
6021381 Reaxys Registry Number Reaxys
80210-62-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17698631 PubMed citation ChEMBL
20606336 PubMed citation Europe PMC
20821175 PubMed citation Europe PMC
21395603 PubMed citation Europe PMC
21420838 PubMed citation Europe PMC
21455420 PubMed citation Europe PMC
21509928 PubMed citation Europe PMC
21569093 PubMed citation Europe PMC
21667000 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
Last Modified
06 March 2018