CHEBI:131733 - penamecillin

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ChEBI Name penamecillin
ChEBI ID CHEBI:131733
Definition A penicillanic acid ester that is the acetoxymethyl ester of benzylpenicillin. It is a prodrug for benzylpenicillin.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kevin
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Formula C19H22N2O6S
Net Charge 0
Average Mass 406.455
Monoisotopic Mass 406.120
InChI InChI=1S/C19H22N2O6S/c1-11(22)26-10-27-18(25)15-19(2,3)28-17-14(16(24)21(15)17)20-13(23)9-12-7-5-4-6-8-12/h4-8,14-15,17H,9-10H2,1-3H3,(H,20,23)/t14-,15+,17-/m1/s1
InChIKey NLOOMWLTUVBWAW-HLLBOEOZSA-N
SMILES C=1C=CC=C(C1)CC(N[C@]2([C@@]3(N(C2=O)[C@](C(S3)(C)C)(C(OCOC(=O)C)=O)[H])[H])[H])=O
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
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 penamecillin (CHEBI:131733) has functional parent benzylpenicillin (CHEBI:18208)
penamecillin (CHEBI:131733) has role antibacterial drug (CHEBI:36047)
penamecillin (CHEBI:131733) has role prodrug (CHEBI:50266)
penamecillin (CHEBI:131733) is a penicillanic acid ester (CHEBI:51212)
penamecillin (CHEBI:131733) is a semisynthetic derivative (CHEBI:72588)
IUPAC Name
acetoxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
INNs Sources
penamecilina WHO MedNet
penamecillin WHO MedNet
pénamécilline WHO MedNet
penamecillinum WHO MedNet
Synonyms Sources
Acetoxymethyl benzylpenicillanate ChemIDplus
Benzylpenicillin acetoxymethyl ester ChemIDplus
Manual Xrefs Databases
2077 DrugCentral
D05406 KEGG DRUG
GB1003479 Patent
Penamecillin Wikipedia
US3250679 Patent
View more database links
Registry Numbers Types Sources
5164412 Reaxys Registry Number Reaxys
983-85-7 CAS Registry Number ChemIDplus
983-85-7 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
15214080 PubMed citation Europe PMC
19108231 PubMed citation Europe PMC
4959939 PubMed citation Europe PMC
6791463 PubMed citation Europe PMC
Last Modified
22 February 2017