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ChEBI
> Main
CHEBI:8255 - pivampicillin
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ChEBI Ontology
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ChEBI Name
pivampicillin
ChEBI ID
CHEBI:8255
Definition
A penicillanic acid ester that is the pivaloyloxymethyl ester of ampicillin. It is a prodrug of ampicillin.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C22H29N3O6S
Net Charge
0
Average Mass
463.54828
Monoisotopic Mass
463.17771
InChI
InChI=1S/C22H29N3O6S/c1-
21(2,3)
20(29)
31-
11-
30-
19(28)
15-
22(4,5)
32-
18-
14(17(27)
25(15)
18)
24-
16(26)
13(23)
12-
9-
7-
6-
8-
10-
12/h6-
10,13-
15,18H,11,23H2,1-
5H3,(H,24,26)
/t13-
,14-
,15+,18-
/m1/s1
InChIKey
ZEMIJUDPLILVNQ-ZXFNITATSA-N
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1)C(=O)OCOC(=O)C(C)(C)C
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
pivampicillin (
CHEBI:8255
)
has functional parent
ampicillin (
CHEBI:28971
)
pivampicillin (
CHEBI:8255
)
has role
prodrug (
CHEBI:50266
)
pivampicillin (
CHEBI:8255
)
is a
penicillanic acid ester (
CHEBI:51212
)
pivampicillin (
CHEBI:8255
)
is a
pivaloyloxymethyl ester (
CHEBI:136685
)
IUPAC Name
[(2,2-
dimethylpropanoyl)oxy]methyl 6β-
[(2
R
)-
2-
amino-
2-
phenylacetamido]-
2,2-
dimethylpenam-
3α-
carboxylate
INNs
Sources
pivampicilina
ChemIDplus
pivampicillin
ChemIDplus
pivampicilline
ChemIDplus
pivampicillinum
ChemIDplus
Synonyms
Sources
ampicillin pivaloyloxymethyl ester
ChemIDplus
pivaloyloxymethyl ampicillinate
ChemIDplus
Manual Xrefs
Databases
2218
DrugCentral
C11750
KEGG COMPOUND
CN101612154
Patent
D08396
KEGG DRUG
DB01604
DrugBank
LSM-6580
LINCS
Pivampicillin
Wikipedia
US3660575
Patent
View more database links
Registry Numbers
Types
Sources
33817-20-8
CAS Registry Number
ChemIDplus
5406076
Beilstein Registry Number
Beilstein
Citations
Types
Sources
10830765
PubMed citation
Europe PMC
15793098
PubMed citation
Europe PMC
21144541
PubMed citation
Europe PMC
29017833
PubMed citation
Europe PMC
3465515
PubMed citation
Europe PMC
Last Modified
14 March 2018