CHEBI:3505 - cefpodoxime proxetil

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ChEBI Name cefpodoxime proxetil
ChEBI ID CHEBI:3505
Definition The 1-[(isopropoxycarbonyl)oxy]ethyl (proxetil) ester prodrug of cefpodoxime. After swallowing, hydrolysis of the ester group occurs in the intestinal epithelium, to release active cefpodoxime in the bloodstream. It is used to treat acute otitis media, pharyngitis, and sinusitis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H27N5O9S2
Net Charge 0
Average Mass 557.59700
Monoisotopic Mass 557.12502
InChI InChI=1S/C21H27N5O9S2/c1-9(2)33-21(30)35-10(3)34-19(29)15-11(6-31-4)7-36-18-14(17(28)26(15)18)24-16(27)13(25-32-5)12-8-37-20(22)23-12/h8-10,14,18H,6-7H2,1-5H3,(H2,22,23)(H,24,27)/b25-13-/t10?,14-,18-/m1/s1
InChIKey LTINZAODLRIQIX-FBXRGJNPSA-N
SMILES [H][C@]12SCC(COC)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\c1csc(N)n1)C(=O)OC(C)OC(=O)OC(C)C
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): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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 cefpodoxime proxetil (CHEBI:3505) has functional parent 4-{((R)-2-Carboxy-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-7-ylcarbamoyl)-[(Z)-methoxyimino]-methyl}-thiazol-2-yl-ammonium (CHEBI:417636)
cefpodoxime proxetil (CHEBI:3505) has functional parent cefpodoxime (CHEBI:3504)
cefpodoxime proxetil (CHEBI:3505) has role antibacterial drug (CHEBI:36047)
cefpodoxime proxetil (CHEBI:3505) has role prodrug (CHEBI:50266)
cefpodoxime proxetil (CHEBI:3505) is a carboxylic acid (CHEBI:33575)
cefpodoxime proxetil (CHEBI:3505) is a carboxylic ester (CHEBI:33308)
cefpodoxime proxetil (CHEBI:3505) is a cephalosporin (CHEBI:23066)
IUPAC Names
1-{[(propan-2-yloxy)carbonyl]oxy}ethyl (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-carboxylate
1-{[(propan-2-yloxy)carbonyl]oxy}ethyl 7β-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-3,4-didehydrocepham-4-carboxylate
Synonyms Sources
(RS)-1-((isopropoxycarbonyl)oxy)ethyl (+)-(6R,7R)-7-(2-(2-amino-4-thiazolyl)-2-((Z)-methoxyimino)acetamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate ChemIDplus
cefpodoxime 1-(isopropyloxycarbonyloxy)ethyl ester ChEBI
Manual Xrefs Databases
555 DrugCentral
C08115 KEGG COMPOUND
D00920 KEGG DRUG
DB01416 DrugBank
EP49118 Patent
US4486425 Patent
View more database links
Registry Numbers Types Sources
8174918 Beilstein Registry Number Beilstein
87239-81-4 CAS Registry Number ChemIDplus
Last Modified
22 February 2017