CHEBI:3716 - cinoxacin

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ChEBI Name cinoxacin
ChEBI ID CHEBI:3716
Definition A member of the class of cinnolines that is 6,7-methylenedioxycinnolin-4(1H)-one bearing an ethyl group at position 1 and a carboxylic acid group at position 3. An analogue of oxolinic acid, it has similar antibacterial actions. It was formerly used for the treatment of urinary tract infections.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:314701
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Formula C12H10N2O5
Net Charge 0
Average Mass 262.21820
Monoisotopic Mass 262.059
InChI InChI=1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)
InChIKey VDUWPHTZYNWKRN-UHFFFAOYSA-N
SMILES CCn1nc(C(O)=O)c(=O)c2cc3OCOc3cc12
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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cinoxacin (CHEBI:3716) has role antibacterial drug (CHEBI:36047)
cinoxacin (CHEBI:3716) has role antiinfective agent (CHEBI:35441)
cinoxacin (CHEBI:3716) is a cinnolines (CHEBI:38770)
cinoxacin (CHEBI:3716) is a oxacycle (CHEBI:38104)
cinoxacin (CHEBI:3716) is a oxo carboxylic acid (CHEBI:25754)
IUPAC Name
1-ethyl-4-oxo-1,4-dihydro[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
INNs Sources
cinoxacin ChemIDplus
cinoxacine ChemIDplus
cinoxacino ChemIDplus
cinoxacinum ChemIDplus
Synonyms Sources
1-ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid ChemIDplus
5-Ethyl-8-oxo-5,8-dihydro-1,3-dioxa-5,6-diaza-cyclopenta[b]naphthalene-7-carboxylic acid ChEMBL
Manual Xrefs Databases
1881 VSDB
657 DrugCentral
Cinoxacin Wikipedia
D00872 KEGG DRUG
DB00827 DrugBank
DE2005104 Patent
HMDB0014965 HMDB
LSM-6552 LINCS
US3669965 Patent
US6441167 Patent
View more database links
Registry Numbers Types Sources
1084304 Beilstein Registry Number Beilstein
28657-80-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12204384 PubMed citation Europe PMC
16295658 PubMed citation Europe PMC
29438107 PubMed citation Europe PMC
3005575 PubMed citation ChEMBL
3147004 PubMed citation Europe PMC
6226270 PubMed citation Europe PMC
Last Modified
19 June 2018
General Comment
2014-06-26 Cinoxacin can be found in blood and urine samples of individuals who have taken this drug.