CHEBI:100241 - ciprofloxacin

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ChEBI Name ciprofloxacin
ChEBI ID CHEBI:100241
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 331.133
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)
InChIKey MYSWGUAQZAJSOK-UHFFFAOYSA-N
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 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 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (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.
xenobiotic
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 5.99.1.3 [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)
IUPAC Name
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-YL-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID PDBeChem
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
Database Links Databases
659 DrugCentral
C05349 KEGG COMPOUND
Ciprofloxacin Wikipedia
CPF PDBeChem
D00186 KEGG DRUG
DB00537 DrugBank
DE3142854 Patent
HMDB0014677 HMDB
LSM-5226 LINCS
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.