CHEBI:3393 - carbenicillin

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ChEBI Name carbenicillin
ChEBI ID CHEBI:3393
Definition A penicillin antibiotic having a 6β-2-carboxy-2-phenylacetamido side-chain.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C17H18N2O6S
Net Charge 0
Average Mass 378.40070
Monoisotopic Mass 378.089
InChI InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1
InChIKey FPPNZSSZRUTDAP-UWFZAAFLSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C(C(O)=O)c1ccccc1)C(O)=O
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.
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ChEBI Ontology
Outgoing carbenicillin (CHEBI:3393) has role antibacterial drug (CHEBI:36047)
carbenicillin (CHEBI:3393) is a penicillin (CHEBI:17334)
carbenicillin (CHEBI:3393) is conjugate acid of carbenicillin(2−) (CHEBI:51897)
Incoming carfecillin (CHEBI:3414) has functional parent carbenicillin (CHEBI:3393)
carbenicillin(2−) (CHEBI:51897) is conjugate base of carbenicillin (CHEBI:3393)
carbenicilloyl group (CHEBI:55468) is substituent group from carbenicillin (CHEBI:3393)
IUPAC Name
6β-(2-carboxy-2-phenylacetamido)-2,2-dimethylpenam-3α-carboxylic acid
INNs Sources
carbenicilina DrugBank
carbenicillin KEGG DRUG
carbenicilline DrugBank
carbenicillinum DrugBank
Synonyms Sources
(2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
α-carboxybenzylpencillin ChemIDplus
α-phenyl(carboxymethylpenicillin) ChemIDplus
carboxybenzylpenicillin DrugBank
CBPC ChEBI
N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamic acid ChemIDplus
Manual Xrefs Databases
492 DrugCentral
C06869 KEGG COMPOUND
Carbenicillin Wikipedia
D07614 KEGG DRUG
DB00578 DrugBank
HMDB0014717 HMDB
US3142673 Patent
View more database links
Registry Numbers Types Sources
1230663 Beilstein Registry Number Beilstein
1230663 Reaxys Registry Number Reaxys
4697-36-3 CAS Registry Number KEGG COMPOUND
4697-36-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12569987 PubMed citation Europe PMC
22648337 PubMed citation Europe PMC
6176550 PubMed citation Europe PMC
Last Modified
22 February 2017