CHEBI:135748 - lenampicillin

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ChEBI Name lenampicillin
ChEBI ID CHEBI:135748
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C21H23N3O7S
Net Charge 0
Average Mass 461.490
Monoisotopic Mass 461.12567
InChI InChI=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
InChIKey ZKUKMWMSYCIYRD-ZXFNITATSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCC1=C(C)OC(=O)O1
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
lenampicilina WHO MedNet
lenampicillin ChemIDplus
lénampicilline WHO MedNet
lenampicillinum WHO MedNet
Synonyms Sources
ampicillin 5-methyl-2-oxo-1,3-dioxol-4-yl methyl ester ChEBI
KBT 1585 DrugCentral
KBT-1585 DrugCentral
Manual Xrefs Databases
1553 DrugCentral
D08110 KEGG DRUG
View more database links
Registry Number Type Source
86273-18-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
23 October 2020