CHEBI:2968 - bacampicillin

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ChEBI Name bacampicillin
ChEBI ID CHEBI:2968
Definition A penicillanic acid ester that is the 1-ethoxycarbonyloxyethyl ester of ampicillin. It is a semi-synthetic, microbiologically inactive prodrug of ampicillin.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H27N3O7S
Net Charge 0
Average Mass 465.52110
Monoisotopic Mass 465.157
InChI InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
InChIKey PFOLLRNADZZWEX-FFGRCDKISA-N
SMILES [H][C@]12SC(C)(C)[C@@]([H])(N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1)C(=O)OC(C)OC(=O)OCC
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.
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ChEBI Ontology
Outgoing bacampicillin (CHEBI:2968) has functional parent ampicillin (CHEBI:28971)
bacampicillin (CHEBI:2968) has role prodrug (CHEBI:50266)
bacampicillin (CHEBI:2968) is a penicillanic acid ester (CHEBI:51212)
Incoming bacampicillin hydrochloride (CHEBI:2969) has part bacampicillin (CHEBI:2968)
IUPAC Name
1-[(ethoxycarbonyl)oxy]ethyl 6β-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3α-carboxylate
INNs Sources
bacampicilina ChemIDplus
bacampicillin KEGG DRUG
bacampicilline ChemIDplus
Synonyms Sources
1'-ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanate ChemIDplus
1-[(ethoxycarbonyl)oxy]ethyl (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 IUPAC
bacampicillinum ChemIDplus
Manual Xrefs Databases
280 DrugCentral
Bacampicillin Wikipedia
C08122 KEGG COMPOUND
D07487 KEGG DRUG
DB01602 DrugBank
DE2144457 Patent
HMDB0015540 HMDB
US3873521 Patent
US3939270 Patent
View more database links
Registry Numbers Types Sources
50972-17-3 CAS Registry Number KEGG COMPOUND
50972-17-3 CAS Registry Number ChemIDplus
5784318 Reaxys Registry Number Reaxys
5784318 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
1211909 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
464583 PubMed citation Europe PMC
7012993 PubMed citation Europe PMC
7012998 PubMed citation Europe PMC
9131470 PubMed citation Europe PMC
Last Modified
14 March 2018