CHEBI:51210 - pivmecillinam

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ChEBI Name pivmecillinam
ChEBI ID CHEBI:51210
Definition A penicillanic acid ester that is the [(2,2-dimethylpropanoyl)oxy]methyl ester and prodrug of mecillinam.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H33N3O5S
Net Charge 0
Average Mass 439.56994
Monoisotopic Mass 439.214
InChI InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1
InChIKey NPGNOVNWUSPMDP-HLLBOEOZSA-N
SMILES [H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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.
antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
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 pivmecillinam (CHEBI:51210) has functional parent mecillinam (CHEBI:51208)
pivmecillinam (CHEBI:51210) has role antibacterial drug (CHEBI:36047)
pivmecillinam (CHEBI:51210) has role antiinfective agent (CHEBI:35441)
pivmecillinam (CHEBI:51210) has role prodrug (CHEBI:50266)
pivmecillinam (CHEBI:51210) is a penicillanic acid ester (CHEBI:51212)
pivmecillinam (CHEBI:51210) is a penicillin (CHEBI:17334)
pivmecillinam (CHEBI:51210) is a pivaloyloxymethyl ester (CHEBI:136685)
Incoming pivmecillinam hydrochloride (CHEBI:51213) has part pivmecillinam (CHEBI:51210)
IUPAC Name
[(2,2-dimethylpropanoyl)oxy]methyl 6β-[(azepan-1-ylmethylidene)amino]-2,2-dimethylpenam-3α-carboxylate
INNs Sources
pivmecilinamo ChemIDplus
pivmecillinam ChemIDplus
pivmecillinamum ChemIDplus
Synonyms Sources
[(2,2-dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate IUPAC
amdinocillin pivoxil ChemIDplus
amdinocillin, pivaloyloxymethyl ester ChEBI
Manual Xrefs Databases
DB01605 DrugBank
DE2055531 Patent
LSM-3494 LINCS
US3957764 Patent
View more database links
Registry Numbers Types Sources
32886-97-8 CAS Registry Number ChemIDplus
9014155 Beilstein Registry Number Beilstein
Last Modified
15 March 2018