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CHEBI:135748 - lenampicillin

ChEBI IDCHEBI:135748
ChEBI Namelenampicillin
Stars
DefinitionA penicillanic acid ester that is the (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester of ampicillin. It is a prodrug of ampicillin.
Last Modified23 October 2020
DownloadsMolfile
FormulaC21H23N3O7S
Net Charge0
Average Mass461.496
Monoisotopic Mass461.12567
SMILES[H][C@]12SC(C)(C)[C@H](C(=O)OCc3oc(=O)oc3C)N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1
InChIInChI=1S/C21H23N3O7S/c1-10-12(31-20(28)30-10)9-29-19(27)15-21(2,3)32-18-14(17(26)24(15)18)23-16(25)13(22)11-7-5-4-6-8-11/h4-8,13-15,18H,9,22H2,1-3H3,(H,23,25)/t13-,14-,15+,18-/m1/s1
InChIKeyZKUKMWMSYCIYRD-ZXFNITATSA-N
Roles Classification
Biological Role:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
lenampicillin (CHEBI:135748) has functional parent ampicillin (CHEBI:28971)
lenampicillin (CHEBI:135748) has role prodrug (CHEBI:50266)
lenampicillin (CHEBI:135748) is a ketene acetal (CHEBI:145408)
lenampicillin (CHEBI:135748) is a penicillanic acid ester (CHEBI:51212)
IUPAC Name 
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
INNs  Source
lenampicilinaWHO MedNet
lenampicillinChemIDplus
lénampicillineWHO MedNet
lenampicillinumWHO MedNet
Synonyms  Source
ampicillin 5-methyl-2-oxo-1,3-dioxol-4-yl methyl esterChEBI
KBT 1585DrugCentral
KBT-1585DrugCentral
Manual XrefsDatabases
1553DrugCentral
D08110KEGG DRUG
Registry NumbersSources
CAS:86273-18-9ChemIDplus
Citations