CHEBI:100241 - ciprofloxacin

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ChEBI Name ciprofloxacin
Definition A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:102718, CHEBI:41638, CHEBI:3717
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Formula C17H18FN3O3
Net Charge 0
Average Mass 331.34150
Monoisotopic Mass 331.13322
InChI InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)
SMILES OC(=O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
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.
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 )
topoisomerase IV inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase IV, which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
antibacterial drug
A drug used to treat or prevent bacterial infections.
EC [DNA topoisomerase (ATP-hydrolysing)] inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ciprofloxacin (CHEBI:100241) has role antibacterial drug (CHEBI:36047)
ciprofloxacin (CHEBI:100241) has role antiinfective agent (CHEBI:35441)
ciprofloxacin (CHEBI:100241) has role antimicrobial agent (CHEBI:33281)
ciprofloxacin (CHEBI:100241) has role DNA synthesis inhibitor (CHEBI:59517)
ciprofloxacin (CHEBI:100241) has role EC [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
ciprofloxacin (CHEBI:100241) has role environmental contaminant (CHEBI:78298)
ciprofloxacin (CHEBI:100241) has role topoisomerase IV inhibitor (CHEBI:53559)
ciprofloxacin (CHEBI:100241) has role xenobiotic (CHEBI:35703)
ciprofloxacin (CHEBI:100241) is a N-arylpiperazine (CHEBI:46848)
ciprofloxacin (CHEBI:100241) is a aminoquinoline (CHEBI:36709)
ciprofloxacin (CHEBI:100241) is a fluoroquinolone antibiotic (CHEBI:87211)
ciprofloxacin (CHEBI:100241) is a quinolinemonocarboxylic acid (CHEBI:26512)
ciprofloxacin (CHEBI:100241) is a quinolone (CHEBI:23765)
ciprofloxacin (CHEBI:100241) is a quinolone antibiotic (CHEBI:86324)
Incoming ciprofloxacin hydrochloride (anhydrous) (CHEBI:310388) has part ciprofloxacin (CHEBI:100241)
1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
INNs Sources
ciprofloxacin ChemIDplus
ciprofloxacine ChemIDplus
ciprofloxacino ChemIDplus
ciprofloxacinum ChemIDplus
Synonyms Sources
1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid ChemIDplus
1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid ChEMBL
1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-quinoline-3-carboxylic acid ChEMBL
1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid ChEMBL
1-Cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ChEMBL
1-cyclopropyl-6-fluoro-7-hexahydro-1-pyrazinyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid ChEMBL
Ciprofloxacin KEGG COMPOUND
ciprofloxacin ChEMBL
Manual Xrefs Databases
1763 VSDB
659 DrugCentral
Ciprofloxacin Wikipedia
DB00537 DrugBank
DE3142854 Patent
HMDB0014677 HMDB
US4670444 Patent
View more database links
Registry Numbers Types Sources
3568352 Reaxys Registry Number Reaxys
3568352 Beilstein Registry Number Beilstein
85721-33-1 CAS Registry Number KEGG COMPOUND
85721-33-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10397494 PubMed citation ChEMBL
10737746 PubMed citation ChEMBL
Last Modified
22 February 2017
General Comment
2011-03-17 A second generation fluoroquinolone antibacterial, ciprofloxacin works by interfering with the enzymes that cause DNA to rewind after being copied, so stopping DNA and protein synthesis.