Services
Research
Training
Industry
About us
ChEBI
Examples:
iron*
,
InChI=1S/CH4O/c1-2/h2H,1H3
,
caffeine
Advanced
Home
Advanced Search
Browse
Documentation
Download
Tools
About ChEBI
Submit
Contact us
DiNA
Statistics
Entity of the Month
Periodic Table
Ontology
Train online
User Manual
Annotation Manual
Developer Manual
FAQ's
BiNChE
libChEBI
Web Services
ChEBI
> Main
CHEBI:131733 - penamecillin
Main
ChEBI Ontology
Automatic Xrefs
Reactions
Pathways
Models
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
Supplier Information
Download
Molfile
XML
SDF
Find compounds which contain this structure
Find compounds which resemble this structure
Take structure to the Advanced Search
more structures >>
Molfile
Molfile
Wikipedia
License
Read full article at Wikipedia
Formula
C19H22N2O6S
Net Charge
0
Average Mass
406.455
Monoisotopic Mass
406.11986
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.
View more via ChEBI Ontology
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 (2
S
,5
R
,6
R
)-
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
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