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CHEBI:2968 - bacampicillin

ChEBI IDCHEBI:2968
ChEBI Namebacampicillin
Stars
DefinitionA penicillanic acid ester that is the 1-ethoxycarbonyloxyethyl ester of ampicillin. It is a semi-synthetic, microbiologically inactive prodrug of ampicillin.
Last Modified14 March 2018
DownloadsMolfile
FormulaC21H27N3O7S
Net Charge0
Average Mass465.528
Monoisotopic Mass465.15697
SMILES[H][C@]12SC(C)(C)[C@]([H])(C(=O)OC(C)OC(=O)OCC)N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1
InChIInChI=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
InChIKeyPFOLLRNADZZWEX-FFGRCDKISA-N
Wikipedia
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)
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 Relation(s)
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  Source
bacampicilinaChemIDplus
bacampicillinKEGG DRUG
bacampicillineChemIDplus
Synonyms  Source
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-carboxylateIUPAC
1'-ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanateChemIDplus
bacampicillinumChemIDplus
Manual XrefsDatabases
280DrugCentral
BacampicillinWikipedia
C08122KEGG COMPOUND
D07487KEGG DRUG
DB01602DrugBank
DE2144457Patent
HMDB0015540HMDB
US3873521Patent
US3939270Patent
Registry NumbersSources
Reaxys:5784318Reaxys
CAS:50972-17-3ChemIDplus
CAS:50972-17-3KEGG COMPOUND
Citations