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Identification
Name Ciprofloxacin
Accession Number DB00537 (APRD00424, EXPT00999)
Type small molecule
Groups approved
Description

A broad-spectrum antimicrobial carboxyfluoroquinoline. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • ciprofloxacin
  • Ciprofloxacin dihydrochloride
  • Ciprofloxacin HCl
  • Ciprofloxacin hydrochloride
  • Ciprofloxacin monohydrochloride
  • Ciprofloxacina
Brand names
  • Bacquinor
  • Baycip
  • Bernoflox
  • Ciflox
  • Cifloxin
  • Ciloxan
  • Ciprinol
  • Cipro
  • Cipro I.V.
  • Cipro XL
  • Cipro XR
  • Ciprobay
  • Ciprocinol
  • Ciprodar
  • Cipromycin
  • Ciproquinol
  • Ciproxan
  • Ciproxin
  • Flociprin
  • Floxin
  • Ocuflox
  • Proquin XR
  • Septicide
  • Velomonit
Brand name mixtures
  • Cipro HC Otic Suspension (Ciprofloxacin hydrochloride + Hydrocortisone)
  • Ciprodex (Ciprofloxacin hydrochloride + Dexamethasone)
Categories
  • Anti-Infective Agents
  • Anti-Infectives
  • Quinolones
  • Nucleic Acid Synthesis Inhibitors
CAS number 85721-33-1
Weight Average: 331.3415
Monoisotopic: 331.133219662
Chemical Formula C17H18FN3O3
InChI Key InChIKey=MYSWGUAQZAJSOK-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
SMILES
OC(=O)C1=CN(C2CC2)C2=C(C=C(F)C(=C2)N2CCNCC2)C1=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Fluoroquinolones and Quinolones
  • Aminoquinolines and Derivatives
Substructures
  • Hydroxy Compounds
  • Acetates
  • Aliphatic and Aryl Amines
  • Pyridines and Derivatives
  • Piperazines
  • Fluoroquinolones and Quinolones
  • Cyclopropane and Derivatives
  • Benzene and Derivatives
  • Aminoquinolines and Derivatives
  • Carboxylic Acids and Derivatives
  • Halobenzenes
  • Heterocyclic compounds
  • Aromatic compounds
  • (Iso)quinolines and Derivatives
  • Aryl Halides
  • Anilines
Pharmacology
Indication For the treatment of the following infections caused by susceptible organisms: urinary tract infections, acute uncomplicated cystitis, chronic bacterial prostatitis, lower respiratory tract infections, acute sinusitis, skin and skin structure infections, bone and joint infections, complicated intra-abdominal infections (used in combination with metronidazole), infectious diarrhea, typhoid fever (enteric fever), uncomplicated cervical and urethral gonorrhea, and inhalational anthrax (post-exposure).
Pharmacodynamics Ciprofloxacin is a broad-spectrum antiinfective agent of the fluoroquinolone class. Ciprofloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. The mechanism of action of quinolones, including ciprofloxacin, is different from that of other antimicrobial agents such as beta-lactams, macrolides, tetracyclines, or aminoglycosides; therefore, organisms resistant to these drugs may be susceptible to ciprofloxacin. There is no known cross-resistance between ciprofloxacin and other classes of antimicrobials. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian.
Mechanism of action The bactericidal action of ciprofloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, strand supercoiling repair, and recombination.
Absorption Rapidly and well absorbed from the gastrointestinal tract after oral administration. The absolute bioavailability is approximately 70% with no substantial loss by first pass metabolism.
Volume of distribution Not Available
Protein binding 20 to 40%
Metabolism

Hepatic. Four metabolites have been identified in human urine which together account for approximately 15% of an oral dose. The metabolites have antimicrobial activity, but are less active than unchanged ciprofloxacin.
Route of elimination Approximately 40 to 50% of an orally administered dose is excreted in the urine as unchanged drug.
Half life 4 hours
Clearance
  • Renal cl=300 mL/min
Toxicity The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Bayer healthcare pharmaceuticals inc
  • Bayer pharmaceuticals corp
  • App pharmaceuticals llc
  • Bedford laboratories
  • Claris lifesciences ltd
  • Hospira inc
  • Teva parenteral medicines inc
  • West ward pharmaceutical corp
  • Hikma farmaceutica (portugal) sa
  • Acs dobfar info sa
  • Baxter healthcare corp
  • Bedford laboratories div ben venue laboratories inc
  • Alcon inc
  • Akorn inc
  • Bausch and lomb pharmaceuticals inc
  • Fdc ltd
  • Hitech pharmacal corp
  • Nexus pharmaceuticals inc
  • Novex pharma
  • Pharmaforce inc
  • Wraser pharmaceuticals llc
  • Depomed inc
  • Apotex inc
  • Aurobindo pharma ltd
  • Barr laboratories inc
  • Carlsbad technology inc
  • Dr reddys laboratories ltd
  • Hikma pharmaceuticals
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Nostrum laboratories inc
  • Pliva inc
  • Ranbaxy pharmaceuticals inc
  • Sandoz inc
  • Taro pharmaceuticals usa inc
  • Teva pharmaceuticals usa inc
  • Unique pharmaceutical laboratories
  • Watson laboratories inc
  • Allergan inc
Packagers
Dosage forms
Form Route Strength
Ointment Ophthalmic
Solution Intravenous
Solution Ophthalmic
Suspension Oral
Tablet Oral
Tablet, extended release Oral
Prices
Unit description Cost Unit
Cipro 400 mg Solution 40ml Vial 259.99 USD vial
Floxin Otic 0.3% Solution 10ml Bottle 142.91 USD bottle
Cipro 500 mg/5ml(10%) Suspension 100ml Bottle 136.75 USD bottle
Cipro HC 0.2-1% Suspension 10ml Bottle 131.54 USD bottle
Cipro 250 mg/5ml(5%) Suspension 100ml Bottle 116.8 USD bottle
Ocuflox 0.3% Solution 10ml Bottle 106.09 USD bottle
Ciprofloxacin HCl 0.3% Solution 10ml Bottle 98.22 USD bottle
Ciloxan 0.3% Ointment 3.5 gm Tube 87.49 USD tube
Floxin Otic 0.3% Solution 5ml Bottle 86.49 USD bottle
Ciloxan 0.3% Solution 5ml Bottle 68.33 USD bottle
Ocuflox 0.3% Solution 5ml Bottle 57.32 USD bottle
Ciprofloxacin HCl 0.3% Solution 5ml Bottle 49.2 USD bottle
ProQuin XR 3 500 mg 24 Hour tablet Disp Pack 39.99 USD disp
Ciprofloxacin HCl 0.3% Solution 2.5ml Bottle 26.03 USD bottle
Ciloxan 0.3% eye drops 13.33 USD ml
Ciprofloxacin 0.3% eye drop 12.96 USD ml
Cipro hc otic suspension 12.65 USD ml
Proquin xr 500 mg tablet 12.18 USD tablet
Cipro xr 1000 mg tablet 11.91 USD tablet
Ciprofloxacin-Ciproflox HCl 1000 mg 24 Hour tablet 11.6 USD tablet
Ocuflox 0.3% eye drops 11.35 USD ml
ProQuin XR 500 mg 24 Hour tablet 11.18 USD tablet
Ciprofloxacin er 1000 mg tablet 11.16 USD tablet
Cipro XR 500 mg 24 Hour tablet 10.88 USD tablet
Cipro XR 1000 mg 24 Hour tablet 10.75 USD tablet
Cipro xr 500 mg tablet 10.46 USD tablet
Ciprofloxacin-Ciproflox HCl 500 mg 24 Hour tablet 10.19 USD tablet
Ciprofloxacin er 500 mg tablet 9.8 USD tablet
Floxin 400 mg tablet 9.55 USD tablet
Cetraxal 0.2% ear solution 7.14 USD each
Floxin 200 mg tablet 6.6 USD tablet
Cipro 750 mg tablet 6.26 USD tablet
Cipro 500 mg tablet 6.08 USD tablet
Ciprofloxacin hcl 750 mg tablet 5.65 USD tablet
Floxin 300 mg tablet 5.61 USD tablet
Ciprofloxacin hcl 500 mg tablet 5.59 USD tablet
Cipro 250 mg tablet 5.2 USD tablet
Ciprofloxacin hcl 250 mg tablet 4.59 USD tablet
Floxin otic singles 4.28 USD each
Ciprofloxacin hcl 100 mg tablet 4.17 USD tablet
Ciloxan 0.3 % Solution 2.18 USD ml
Ciprofloxacin hcl powder 1.29 USD g
Apo-Ciproflox 0.3 % Solution 1.18 USD ml
Pms-Ciprofloxacin 0.3 % Solution 1.18 USD ml
Cipro i.v. 10 mg/ml vial 0.72 USD ml
Cipro i.v. 200 mg/100 ml d5w 0.16 USD ml
Ciprofloxacin 200 mg/20 ml vial 0.13 USD ml
Ciprofloxacn-d5w 200 mg/100 ml 0.03 USD ml
Patents
Country Patent Number Approved Expires
United States 7709022 2001-12-23 2021-12-23
United States 5286754 1994-02-15 2011-02-15
Canada 2414271 2005-09-27 2021-06-13
Canada 1330946 1994-07-26 2011-07-26
Properties
State solid
Melting point 255 - 257 oC
Experimental Properties
Property Value Source
water solubility 1.1 mg/L PhysProp
logP 2.3 PhysProp
pKa 6.09 Various sources
Predicted Properties
Property Value Source
water solubility 1.35e+00 g/l ALOGPS
logP -0.57 ALOGPS
logP -1.38 ChemAxon Molconvert
logS -2.39 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 6 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 72.88 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 87.94 ChemAxon Molconvert
polarizability 33.12 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Drusano GL, Standiford HC, Plaisance K, Forrest A, Leslie J, Caldwell J: Absolute oral bioavailability of ciprofloxacin. Antimicrob Agents Chemother. 1986 Sep;30(3):444-6. Pubmed
  2. Hilliard JJ, Krause HM, Bernstein JI, Fernandez JA, Nguyen V, Ohemeng KA, Barrett JF: A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase. Adv Exp Med Biol. 1995;390:59-69. Pubmed
  3. Spivey JM, Cummings DM, Pierson NR: Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy. 1996 Mar-Apr;16(2):314-6. Pubmed
  4. Brouwers JR: Drug interactions with quinolone antibacterials. Drug Saf. 1992 Jul-Aug;7(4):268-81. Pubmed
External Links
Resource Link
KEGG Drug D00186 Link_out
KEGG Compound C05349 Link_out
PubChem Compound 2764 Link_out
PubChem Substance 46504733 Link_out
ChemSpider 2662 Link_out
BindingDB 21690 Link_out
ChEBI 100241 Link_out
ChEMBL 100241 Link_out
Therapeutic Targets Database DAP001360 Link_out
PharmGKB PA449009 Link_out
Drug Product Database 2248439 Link_out
RxList http://www.rxlist.com/cgi/generic/cipro.htm Link_out
Drugs.com http://www.drugs.com/cdi/ciprofloxacin-drops.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cip1082.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Ciprofloxacin Link_out
ATC Codes
  • J01MA02
  • S01AX13
  • S03AA07
  • S02AA15
AHFS Codes
  • 08:12.18
  • 52:04.04
PDB Entries Not Available
FDA label show (119.6 KB)
MSDS show (73.9 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Avoid milk, calcium containing dairy products, iron, magnesium, zinc, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
  • Take with a full glass of water.
  • Take without regard to meals.
Targets

1. DNA topoisomerase 4 subunit A

Pharmacological action: yes
Actions: inhibitor

Topoisomerase IV is essential for chromosome segregation. It has relaxation of supercoiled DNA activity. Performs the decatenation events required during the replication of a circular DNA molecule

Organism class: bacterial
UniProt ID: P43702 Link_out
Gene: parC
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chaudhry U, Ray K, Bala M, Saluja D: Mutation patterns in gyrA and parC genes of ciprofloxacin resistant isolates of Neisseria gonorrhoeae from India. Sex Transm Infect. 2002 Dec;78(6):440-4. Pubmed
  4. Lee JK, Lee YS, Park YK, Kim BS: Mutations in the gyrA and parC genes in ciprofloxacin-resistant clinical isolates of Acinetobacter baumannii in Korea. Microbiol Immunol. 2005;49(7):647-53. Pubmed
  5. Leavis HL, Willems RJ, Top J, Bonten MJ: High-level ciprofloxacin resistance from point mutations in gyrA and parC confined to global hospital-adapted clonal lineage CC17 of Enterococcus faecium. J Clin Microbiol. 2006 Mar;44(3):1059-64. Pubmed
  6. Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92. Pubmed

2. DNA gyrase subunit A

Pharmacological action: yes
Actions: inhibitor

DNA gyrase negatively supercoils closed circular double- stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, including catenanes and knotted rings

Organism class: bacterial
UniProt ID: P43700 Link_out
Gene: gyrA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chaudhry U, Ray K, Bala M, Saluja D: Mutation patterns in gyrA and parC genes of ciprofloxacin resistant isolates of Neisseria gonorrhoeae from India. Sex Transm Infect. 2002 Dec;78(6):440-4. Pubmed
  4. Abdelbaqi K, Menard A, Prouzet-Mauleon V, Bringaud F, Lehours P, Megraud F: Nucleotide sequence of the gyrA gene of Arcobacter species and characterization of human ciprofloxacin-resistant clinical isolates. FEMS Immunol Med Microbiol. 2007 Apr;49(3):337-45. Pubmed
  5. Taylor DE, Chau AS: Cloning and nucleotide sequence of the gyrA gene from Campylobacter fetus subsp. fetus ATCC 27374 and characterization of ciprofloxacin-resistant laboratory and clinical isolates. Antimicrob Agents Chemother. 1997 Mar;41(3):665-71. Pubmed

3. DNA topoisomerase 2-alpha

Pharmacological action: unknown
Actions: inhibitor

Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks

Organism class: human
UniProt ID: P11388 Link_out
Gene: TOP2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Robinson MJ, Martin BA, Gootz TD, McGuirk PR, Osheroff N: Effects of novel fluoroquinolones on the catalytic activities of eukaryotic topoisomerase II: Influence of the C-8 fluorine group. Antimicrob Agents Chemother. 1992 Apr;36(4):751-6. Pubmed
  3. Hussy P, Maass G, Tummler B, Grosse F, Schomburg U: Effect of 4-quinolones and novobiocin on calf thymus DNA polymerase alpha primase complex, topoisomerases I and II, and growth of mammalian lymphoblasts. Antimicrob Agents Chemother. 1986 Jun;29(6):1073-8. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 3A5

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P20815 Link_out
Gene: CYP3A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

3. Cytochrome P450 3A7

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P24462 Link_out
Gene: CYP3A7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

4. Cytochrome P450 1A2

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Transporters

1. Multidrug resistance protein 1

Actions: substrate, inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. Pubmed
  2. Yamaguchi H, Yano I, Saito H, Inui K: Effect of cisplatin-induced acute renal failure on bioavailability and intestinal secretion of quinolone antibacterial drugs in rats. Pharm Res. 2004 Feb;21(2):330-8. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:04

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.