CPF

1-CYCLOPROPYL-6-FLUORO-4-OXO-7-PIPERAZIN-1-YL-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID



Chemical Component Summary

Name1-CYCLOPROPYL-6-FLUORO-4-OXO-7-PIPERAZIN-1-YL-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID
Synonymsciprofloxacin
Identifiers1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-quinoline-3-carboxylic acid
FormulaC17 H18 F N3 O3
Molecular Weight331.342
TypeNON-POLYMER
Isomeric SMILESc1c2c(cc(c1F)N3CCNCC3)N(C=C(C2=O)C(=O)O)C4CC4
InChIInChI=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)
InChIKeyMYSWGUAQZAJSOK-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count42
Chiral Atom Count0
Bond Count45
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB00537 
NameCiprofloxacin
Groups
  • approved
  • investigational
DescriptionCiprofloxacin is a second generation fluoroquinolone that has spawned many derivative antibiotics.[A178870] It is formulated for oral, intravenous, intratympanic, ophthalmic, and otic administration for a number of bacterial infections.[L6469,L6472,L6475,L6478,L6481,L6484,L6487,L6490,L6493] The first ciprofloxacin containing product was FDA approved on 22 October 1987.[L6463]
Synonyms
  • Ciprofloxacinum
  • 1-cyclopropyl-6-fluoro-7-hexahydro-1-pyrazinyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
  • 1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-quinoline-3-carboxylic acid
  • 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
  • Ciprofloxacine
Brand Names
  • Cipro IV 10mg/ml
  • Ciprofloxacin-500
  • Teva-ciprofloxacin
  • Jamp-ciprofloxacin
  • Ciloxan
IndicationCiprofloxacin is only indicated in infections caused by susceptible bacteria.[L6469,L6472,L6475,L6478,L6481,L6484,L6487,L6490,L6493] Ciprofloxacin immediate release tablets, oral suspensions, and intravenous injections are indicated for the treatment of skin and skin structure infections, bone and joint infections, complicated intra-abdominal infections, nosocomial pneumonia, febrile neutropenia, adults who have inhaled anthrax, plague, chronic bacterial prostatitis, lower respiratory tract infections including acute exacerbations of chronic bronchitis, urinary tract infections, complicated urinary tract infections in pediatrics, complicated pyelonephritis in pediatrics, and acute sinusitis.[L6481,L6478] A ciprofloxacin otic solution and otic suspension with hydrocortisone are indicated for acute otitis externa.[L6469,L6484] Ciprofloxacin suspension with dexamethasone is indicated for acute otitis media in pediatric patients with tympanostomy tubes or acute otitis externa.[L6490] A ciprofloxacin intratympanic injection is indicated for pediatric patients with bilateral otitis media with effusion who are having tympanostomy tubes placed or pediatric patients 6 months or older with acute otitis externa.[L6493] A ciprofloxacin eye drop is indicated for bacterial corneal ulcers and conjunctivitis.[L6472] A ciprofloxacin eye ointment is indicated for bacterial conjunctivitis.[L6475] A ciprofloxacin extended release tablet is indicated for uncomplicated urinary tract infections, complicated urinary tract infections, and acute uncomplicated pyelonephritis.[L6487]
Categories
  • Agents Causing Muscle Toxicity
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-Code
  • J01RA11
  • S03AA07
  • J01MA02
  • S02AA15
  • J01RA10
CAS number85721-33-1

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA topoisomerase 4 subunit AMTNINYEGIEQMPLRTFTEKAYLNYSMYVIMDRALPFIGDGLKPVQRRIV...unknowninhibitor
DNA gyrase subunit AMTDSIQSSITPVNIEEELKSSYLDYAMSVIVGRALPDVRDGLKPVHRRVL...unknowninhibitor
DNA topoisomerase 2-alphaMEVSPLQPVNENMQVNKIKKNEDAKKRLSVERIYQKKTQLEHILLRPDTY...unknowninhibitor
Potassium voltage-gated channel subfamily H member 2MPVRRGHVAPQNTFLDTIIRKFEGQSRKFIIANARVENCAVIYCNDGFCE...unknown
DNA gyrase subunit AMSDLAREITPVNIEEELKSSYLDYAMSVIVGRALPDVRDGLKPVHRRVLY...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 4011971, 2764
ChEMBL CHEMBL8
ChEBI CHEBI:100241
CCDC/CSD PEFZIL01, COVPIN03, COVPIN04, COVPIN01, BAFKEA, QUKHIP02, QUKHIP, QUKHOV, QUKHUB, QUKHIP03, COVPIN05, NUWFUI, OXAYUJ, MUGCEZ, DOFWUT01, DOFXOO, KOFFAO, QUKHIP01, QABTOF, ORUZAD, PUNMUJ, QUKHUB01, KEWSIR, OSUQEA, BONZUA, IDARUA, ORUYIK, ORUYOQ, HUSTUN, PUNMIX, MUGCID01, KAFDAX, DOFXII, MUGCID, KOFFES, POTLAN, KEWSOX, KEWSEN, TEKBIU, PEFZIL, QIBBAE, ENODOB, HUSVEZ, JIRYAL, HUSVAV
COD 4502705