CHEBI:192379 - quinacillin

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ChEBI Name quinacillin
ChEBI ID CHEBI:192379
Definition A semisynthetic penicillase-resistant penicillin with antibacterial activity; it binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H16N4O6S
Net Charge 0
Average Mass 416.410
Monoisotopic Mass 416.07906
InChI InChI=1S/C18H16N4O6S/c1-18(2)12(17(27)28)22-14(24)11(15(22)29-18)21-13(23)9-10(16(25)26)20-8-6-4-3-5-7(8)19-9/h3-6,11-12,15H,1-2H3,(H,21,23)(H,25,26)(H,27,28)/t11-,12+,15-/m1/s1
InChIKey GPMSLJIYNWBYEL-TYNCELHUSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(N=C2C=CC=CC2=N1)C(O)=O)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.
allergen
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
(via penicillin )
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing quinacillin (CHEBI:192379) has role antibacterial drug (CHEBI:36047)
quinacillin (CHEBI:192379) is a penicillin (CHEBI:17334)
quinacillin (CHEBI:192379) is a quinoxaline derivative (CHEBI:38771)
IUPAC Name
3-{[(2S,5R,6R)-2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]carbamoyl}quinoxaline-2-carboxylic acid
INNs Sources
quinacilina ChemIDplus
quinacillin ChemIDplus
quinacilline ChemIDplus
quinacillinum ChemIDplus
Synonyms Sources
(2S,5R,6R)-6-[(3-carboxyquinoxaline-2-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid ChEBI
(3-carboxy-2-quinoxalinyl)penicillin ChemIDplus
3-carboxy-2-quinoxalinylpenicillanic acid ChemIDplus
6-(3-Carboxy-2-chinoxalinecarboxamido)-3,3-dimethyl-7-oxo-4-thia-azabicyclo(3.2.0)heptan-2-carbonsaeure ChemIDplus
Manual Xref Database
Quinacillin Wikipedia
View more database links
Registry Number Type Source
1596-63-0 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
4108368 PubMed citation Europe PMC
Last Modified
19 July 2022