CHEBI:7731 - ofloxacin

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ChEBI Name ofloxacin
ChEBI ID CHEBI:7731
Definition An oxazinoquinolone carrying carboxy, fluoro, methyl and 4-methylpiperazino substituents. A synthetic fluoroquinolone antibacterial agent, it inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:100146
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Formula C18H20FN3O4
Net Charge 0
Average Mass 361.36750
Monoisotopic Mass 361.144
InChI InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)
InChIKey GSDSWSVVBLHKDQ-UHFFFAOYSA-N
SMILES CC1COc2c(N3CCN(C)CC3)c(F)cc3c2n1cc(C(O)=O)c3=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
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 quinolone antibiotic )
(via heterocyclic antibiotic )
(via fluoroquinolone antibiotic )
Application(s): antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing ofloxacin (CHEBI:7731) has role antibacterial drug (CHEBI:36047)
ofloxacin (CHEBI:7731) has role antiinfective agent (CHEBI:35441)
ofloxacin (CHEBI:7731) has role DNA synthesis inhibitor (CHEBI:59517)
ofloxacin (CHEBI:7731) is a 3-oxo monocarboxylic acid (CHEBI:47881)
ofloxacin (CHEBI:7731) is a N-alkylpiperazine (CHEBI:46845)
ofloxacin (CHEBI:7731) is a N-arylpiperazine (CHEBI:46848)
ofloxacin (CHEBI:7731) is a fluoroquinolone antibiotic (CHEBI:87211)
ofloxacin (CHEBI:7731) is a organic heterotricyclic compound (CHEBI:26979)
ofloxacin (CHEBI:7731) is a oxazinoquinoline (CHEBI:53665)
ofloxacin (CHEBI:7731) is a quinolone antibiotic (CHEBI:86324)
Incoming levofloxacin (CHEBI:63598) is a ofloxacin (CHEBI:7731)
IUPAC Name
9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid
INNs Sources
ofloxacin KEGG DRUG
ofloxacin ChemIDplus
ofloxacine ChemIDplus
ofloxacino ChemIDplus
ofloxacinum ChemIDplus
Synonyms Sources
8-Fluoro-3-methyl-9-(4-methyl-piperazin-1-yl)-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ChEMBL
OFLX KEGG DRUG
Manual Xrefs Databases
1898 VSDB
1981 DrugCentral
C07321 KEGG COMPOUND
CPD-12843 MetaCyc
D00453 KEGG DRUG
DB01165 DrugBank
HMDB0015296 HMDB
LSM-4370 LINCS
Ofloxacin Wikipedia
View more database links
Registry Numbers Types Sources
3657947 Reaxys Registry Number Reaxys
82419-36-1 CAS Registry Number KEGG COMPOUND
82419-36-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11710934 PubMed citation Europe PMC
15008519 PubMed citation Europe PMC
16669862 PubMed citation Europe PMC
19646516 PubMed citation Europe PMC
24497308 PubMed citation Europe PMC
24550337 PubMed citation Europe PMC
7884650 PubMed citation Europe PMC
Last Modified
22 February 2017