Identification

Name
Ciprofloxacin
Accession Number
DB00537
Description

Ciprofloxacin is a second generation fluoroquinolone that has spawned many derivative antibiotics.9 It is formulated for oral, intravenous, intratympanic, ophthalmic, and otic administration for a number of bacterial infections.18,19,20,21,22,23,24,25,26

The first ciprofloxacin containing product was FDA approved on 22 October 1987.17

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 331.3415
Monoisotopic: 331.133219662
Chemical Formula
C17H18FN3O3
Synonyms
  • 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
  • 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic 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
  • 1-Cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  • 1-cyclopropyl-6-fluoro-7-hexahydro-1-pyrazinyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
  • Ciprofloxacin
  • Ciprofloxacine
  • Ciprofloxacino
  • Ciprofloxacinum
External IDs
  • BAY Q 3939
  • BAY-Q-3939
  • BAYQ3939
  • J01MA02

Pharmacology

Indication

Ciprofloxacin is only indicated in infections caused by susceptible bacteria.18,19,20,21,22,23,24,25,26

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.22,21

A ciprofloxacin otic solution and otic suspension with hydrocortisone are indicated for acute otitis externa.18,23 Ciprofloxacin suspension with dexamethasone is indicated for acute otitis media in pediatric patients with tympanostomy tubes or acute otitis externa.25 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.26

A ciprofloxacin eye drop is indicated for bacterial corneal ulcers and conjunctivitis.19 A ciprofloxacin eye ointment is indicated for bacterial conjunctivitis.20

A ciprofloxacin extended release tablet is indicated for uncomplicated urinary tract infections, complicated urinary tract infections, and acute uncomplicated pyelonephritis.24

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Ciprofloxacin is a second generation fluoroquinolone that is active against many Gram negative and Gram positive bacteria.9,18,19,20,21,22,23,24,25,26 It produces its action through inhibition of bacterial DNA gyrase and topoisomerase IV.12 Ciprofloxacin binds to bacterial DNA gyrase with 100 times the affinity of mammalian DNA gyrase.13 There is no cross resistance between fluoroquinolones and other classes of antibiotics, so it may be of clinical value when other antibiotics are no longer effective.13 Ciprofloxain and its derivatives are also being investigated for its action against malaria, cancers, and AIDS.12

Mechanism of action

Ciprofloxacin acts on bacterial topoisomerase II (DNA gyrase) and topoisomerase IV.12 Ciprofloxacin's targeting of the alpha subunits of DNA gyrase prevents it from supercoiling the bacterial DNA which prevents DNA replication.10,11

TargetActionsOrganism
ADNA topoisomerase 4 subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA gyrase subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
UDNA topoisomerase 2-alpha
inhibitor
Humans
UPotassium voltage-gated channel subfamily H member 2Not AvailableHumans
UDNA gyrase subunit ANot AvailableEscherichia coli (strain K12)
UDNA topoisomerase 4 subunit ANot AvailableStaphylococcus aureus
UDNA topoisomerase 4 subunit BNot AvailableBacillus subtilis (strain 168)
UDNA gyrase subunit ANot AvailableBacillus subtilis (strain 168)
UMultidrug resistance protein MdtKNot AvailableEscherichia coli
UGyrase ANot AvailableMycobacterium tuberculosis
UDNA gyrase subunit ANot AvailableStaphylococcus aureus
Absorption

A 250mg oral dose of ciprofloxacin reaches an average maximum concentration of 0.94mg/L in 0.81 hours with an average area under the curve of 1.013L/h*kg.8 The FDA reports an oral bioavailability of 70-80%Label,1 while other studies report it to be approximately 60%.8 An early review of ciprofloxacin reported an oral bioavailability of 64-85% but recommends 70% for all practical uses.10

Volume of distribution

Cirpofloxacin follws a 3 compartment distribution model with a central compartment volume of 0.161L/kg8 and a total volume of distribution of 2.00-3.04L/kg.10

Protein binding

20-40%.Label,10

Metabolism

Ciprofloxacin is primarily metabolized by CYP1A2.22 The primary metabolites oxociprofloxacin and sulociprofloxacin make up 3-8% of the total dose each.24 Ciprofloxacin is also converted to the minor metabolites desethylene ciprofloxacin and formylciprofloxacin.24 These 4 metabolites account for 15% of a total oral dose.22

There is a lack of available data on the enzymes and types of reactions involved in forming these metabolites.2,3,4,5

Hover over products below to view reaction partners

Route of elimination

27% of an oral dose was recovered unmetabolized in urine compared to 46% of an intravenous dose.8 Collection of radiolabelled ciprofloxacin resulted in 45% recovery in urine and 62% recovery in feces.10

Half-life

The average half life following a 250mg oral dose was 4.71 hours and 3.65 hours following a 100mg intravenous dose.8 Generally the half life is reported as 4 hours.Label,8

Clearance

The average renal clearance after a 250mg oral dose is 5.08mL/min*kg.8 Following a 100mg intravenous dose, the average total clearance is 9.62mL/min*kg, average renal clearance is 4.42mL/min*kg, and average non renal clearance is 5.21mL/min*kg.8

Adverse Effects
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Toxicity

Patients experiencing an overdose may present with nausea, vomiting, abdominal pain, crystalluria, nephrotoxicity, and oliguria.14,15,16 Ciprofloxacin overdose typically leads to acute renal failure.16 An overdose may progress over the next 6 days with rising serum creatinine and BUN, as well as anuria.15 Patients may require prednisone therapy, urgent hemodialysis, or supportive therapy.14,16 Depending on the degree of overdose, patients may recover normal kidney function or progress to chronic kidney failure.16

The oral LD50 in rats is >2000mg/kg.27

Ciprofloxacin for intratympanic injection or otic use has low systemic absorption and so it unlikely to be a risk in pregnancy or lactation.26 There is generally no harm to the fetus in animal studies, however high doses may lead to gastrointestinal disturbances in the mother which may increase the incidence of abortion.25,19,23,20 In human studies there was no increase in fetal malformations above background rates.21,22 The risk and benefit of ciprofloxacin should be weighed in pregnancy and breast feeding.25,19,23,21,22,24,20,18

2/8 in vitro tests and 0/3 in vivo tests of mutagenicity of ciprofloxacin have yielded a positive result.26,25,19,23,21,22,24,20,18

Oral doses of 200 and 300 times the maximum recommended clinical dose in rats and mice have shown no carcinogenicity or tumorigenicity.26,19,23,21,22,24,20,18

Oral doses above the maximum recommended clinical dose have shown no effects on fertility in rats.26,23,21,22,24,20,18

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirCiprofloxacin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Ciprofloxacin.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Ciprofloxacin.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Ciprofloxacin.
AcebutololThe risk or severity of QTc prolongation can be increased when Ciprofloxacin is combined with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Ciprofloxacin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ciprofloxacin which could result in a higher serum level.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Ciprofloxacin.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Ciprofloxacin.
AcetazolamideAcetazolamide may increase the excretion rate of Ciprofloxacin which could result in a lower serum level and potentially a reduction in efficacy.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
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    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid milk and dairy products. Dairy products and calcium fortified juices decrease the absorption of ciprofloxacin.
  • Limit caffeine intake.
  • Take with or without food. The absorption is not significantly affected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ciprofloxacin hydrochloride4BA73M5E3786393-32-0ARPUHYJMCVWYCZ-UHFFFAOYSA-N
Ciprofloxacin lactateUEY6XFC22496186-80-0NRBJWZSFNGZBFQ-UHFFFAOYSA-N
Product Images
International/Other Brands
Bacquinor / Baycip / Ciflox / Cifloxin / Ciprinol / Ciprobay / Ciprocinol / Ciprodar / Ciproxan / Ciproxin / Flociprin / Proquin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act CiprofloxacinTabletOralTEVA Canada Limited2004-02-18Not applicableCanada flag
Act CiprofloxacinTabletOralTEVA Canada Limited2004-02-18Not applicableCanada flag
Act CiprofloxacinTabletOralTEVA Canada Limited2004-02-18Not applicableCanada flag
CetraxalSolution / drops0.5 mg/0.25mLAuricular (otic)Wraser Llc2009-05-14Not applicableUS flag
CiloxanSolution0.3 %OphthalmicNovartis1992-12-31Not applicableCanada flag
CiloxanOintment3 mg/1gOphthalmicALCON LABORATORIES, INC.1998-06-02Not applicableUS flag
CiloxanSolution3.5 mg/1mLOphthalmicPhysicians Total Care, Inc.1995-07-10Not applicableUS flag
CiloxanSolution / drops3 mg/1mLOphthalmicREMEDYREPACK INC.2018-05-30Not applicableUS flag
CiloxanOintment0.3 %OphthalmicNovartis1998-10-07Not applicableCanada flag
CiloxanSolution / drops3 mg/1mLOphthalmicALCON LABORATORIES, INC.1991-01-15Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-ciprofloxacinTabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-ciprofloxacinTabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-ciprofloxacinTabletOralAngita Pharma Inc.2020-01-20Not applicableCanada flag
Apo-ciprofloxTabletOralApotex Corporation2004-02-09Not applicableCanada flag
Apo-ciprofloxTabletOralApotex Corporation2004-02-09Not applicableCanada flag
Apo-ciprofloxSolutionOphthalmicApotex Corporation2005-09-14Not applicableCanada flag
Apo-ciprofloxTabletOralApotex Corporation2004-02-09Not applicableCanada flag
Auro-ciprofloxacinTabletOralAuro Pharma Inc2012-06-132018-12-20Canada flag
Auro-ciprofloxacinTabletOralAuro Pharma Inc2012-06-13Not applicableCanada flag
Auro-ciprofloxacinTabletOralAuro Pharma Inc2012-06-13Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CiproCiprofloxacin (452.2 mg/1) + Ciprofloxacin hydrochloride (574.9 1/1)Tablet, film coated, extended releaseOralBayer HealthCare Pharmaceuticals Inc.2012-10-012016-07-27US flag
CiproCiprofloxacin (212.6 mg/1) + Ciprofloxacin hydrochloride (287.5 1/1)Tablet, film coated, extended releaseOralBayer HealthCare Pharmaceuticals Inc.2012-10-012016-07-27US flag
CiproCiprofloxacin hydrochloride (2 mg/1mL) + Benzyl alcohol (9 mg/1mL) + Hydrocortisone (10 mg/1mL)SuspensionAuricular (otic)Physicians Total Care, Inc.2009-02-12Not applicableUS flag
CiproCiprofloxacin (452.2 mg/1) + Ciprofloxacin hydrochloride (574.9 1/1)Tablet, film coated, extended releaseOralBayer HealthCare Pharmaceuticals Inc.2012-10-012016-07-27US flag
CiproCiprofloxacin (212.6 mg/1) + Ciprofloxacin hydrochloride (287.5 1/1)Tablet, film coated, extended releaseOralBayer HealthCare Pharmaceuticals Inc.2012-10-012016-07-27US flag
Cipro HCCiprofloxacin hydrochloride (2 mg/1mL) + Benzyl alcohol (9 mg/1mL) + Hydrocortisone (10 mg/1mL)SuspensionAuricular (otic)Stat Rx USA1998-02-10Not applicableUS flag
Cipro HCCiprofloxacin hydrochloride (2.0 mg/1mL) + Hydrocortisone (10 mg/1mL)SuspensionAuricular (otic)A-S Medication Solutions1999-03-15Not applicableUS flag
Cipro HCCiprofloxacin hydrochloride (2 mg/1mL) + Hydrocortisone (10 mg/1mL)SuspensionAuricular (otic)ALCON LABORATORIES, INC.1999-03-15Not applicableUS flag
Cipro HC Otic SuspensionCiprofloxacin (2 mg) + Hydrocortisone (10 mg)SuspensionAuricular (otic)Alcon, Inc.1999-06-222008-12-08Canada flag
Cipro XRCiprofloxacin hydrochloride (287.5 mg/1) + Ciprofloxacin (212.6 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2003-01-302011-06-30US flag

Categories

ATC Codes
J01RA11 — Ciprofloxacin and tinidazoleS03AA07 — CiprofloxacinJ01MA02 — CiprofloxacinS02AA15 — CiprofloxacinJ01RA10 — Ciprofloxacin and metronidazoleJ01RA12 — Ciprofloxacin and ornidazoleS01AE03 — Ciprofloxacin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
Fluoroquinolones / N-arylpiperazines / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Benzenoids / Aryl fluorides
show 12 more
Substituents
1,4-diazinane / Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-arylpiperazine, aminoquinoline, quinolone antibiotic, fluoroquinolone antibiotic, quinolone, quinolinemonocarboxylic acid (CHEBI:100241)

Chemical Identifiers

UNII
5E8K9I0O4U
CAS number
85721-33-1
InChI Key
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)
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=CC(N3CCNCC3)=C(F)C=C2C1=O

References

Synthesis Reference
US4670444
General References
  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:3777908]
  2. van Geijlswijk IM, van Zanten AR, van der Meer YG: Reliable new high-performance liquid chromatographic method for the determination of ciprofloxacin in human serum. Ther Drug Monit. 2006 Apr;28(2):278-81. doi: 10.1097/01.ftd.0000189823.43236.90. [PubMed:16628145]
  3. Rusch M, Spielmeyer A, Zorn H, Hamscher G: Biotransformation of ciprofloxacin by Xylaria longipes: structure elucidation and residual antibacterial activity of metabolites. Appl Microbiol Biotechnol. 2018 Oct;102(19):8573-8584. doi: 10.1007/s00253-018-9231-y. Epub 2018 Jul 21. [PubMed:30030566]
  4. Mack G: Improved high-performance liquid chromatographic determination of ciprofloxacin and its metabolites in human specimens. J Chromatogr. 1992 Nov 6;582(1-2):263-7. [PubMed:1491053]
  5. Abadia AR, De Francesco L, Guaitani A: Disposition of ciprofloxacin in the isolated perfused rat liver. Drug Metab Dispos. 1995 Feb;23(2):197-200. [PubMed:7736911]
  6. Takács-Novák K, Józan M, Szász H: Lipophilicity of antibacterial fluoroquinolones International Journal of Pharmaceutics. 1992 Feb 1;79(1-3):89-96.
  7. Torniainen K, Tammilehto S, Ulvi V: The effect of pH, buffer type and drug concentration on the photodegradation of ciprofloxacin International Journal of Pharmaceutics. 1996 Apr 30;132(1):53-61.
  8. Wingender W, Graefe KH, Gau W, Forster D, Beermann D, Schacht P: Pharmacokinetics of ciprofloxacin after oral and intravenous administration in healthy volunteers. Eur J Clin Microbiol. 1984 Aug;3(4):355-9. [PubMed:6489326]
  9. Zhang GF, Liu X, Zhang S, Pan B, Liu ML: Ciprofloxacin derivatives and their antibacterial activities. Eur J Med Chem. 2018 Feb 25;146:599-612. doi: 10.1016/j.ejmech.2018.01.078. Epub 2018 Feb 4. [PubMed:29407984]
  10. LeBel M: Ciprofloxacin: chemistry, mechanism of action, resistance, antimicrobial spectrum, pharmacokinetics, clinical trials, and adverse reactions. Pharmacotherapy. 1988;8(1):3-33. [PubMed:2836821]
  11. Shen LL, Pernet AG: Mechanism of inhibition of DNA gyrase by analogues of nalidixic acid: the target of the drugs is DNA. Proc Natl Acad Sci U S A. 1985 Jan;82(2):307-11. doi: 10.1073/pnas.82.2.307. [PubMed:2982149]
  12. Pietsch F, Bergman JM, Brandis G, Marcusson LL, Zorzet A, Huseby DL, Hughes D: Ciprofloxacin selects for RNA polymerase mutations with pleiotropic antibiotic resistance effects. J Antimicrob Chemother. 2017 Jan;72(1):75-84. doi: 10.1093/jac/dkw364. Epub 2016 Sep 12. [PubMed:27621175]
  13. Varshney A, Ansari Y, Zaidi N, Ahmad E, Badr G, Alam P, Khan RH: Analysis of binding interaction between antibacterial ciprofloxacin and human serum albumin by spectroscopic techniques. Cell Biochem Biophys. 2014 Sep;70(1):93-101. doi: 10.1007/s12013-014-9863-1. [PubMed:24913236]
  14. George MJ, Dew RB 3rd, Daly JS: Acute renal failure after an overdose of ciprofloxacin. Arch Intern Med. 1991 Mar;151(3):620. [PubMed:2001151]
  15. Dharnidharka VR, Nadeau K, Cannon CL, Harris HW, Rosen S: Ciprofloxacin overdose: acute renal failure with prominent apoptotic changes. Am J Kidney Dis. 1998 Apr;31(4):710-2. [PubMed:9531191]
  16. Hajji M, Jebali H, Mrad A, Blel Y, Brahmi N, Kheder R, Beji S, Fatma LB, Smaoui W, Krid M, Hmida FB, Rais L, Zouaghi MK: Nephrotoxicity of Ciprofloxacin: Five Cases and a Review of the Literature. Drug Saf Case Rep. 2018 Apr 18;5(1):17. doi: 10.1007/s40800-018-0073-4. [PubMed:29671145]
  17. FDA Approved Drug Products: Cipro [Link]
  18. FDA Approved Drug Products: Cetraxal Solution/Drops;Otic [Link]
  19. FDA Approved Drug Products: Ciloxan Solution/Drops; Opthmalmic [Link]
  20. FDA Approved Drug Products: Ciloxan Ointment; Opthalmic [Link]
  21. FDA Approved Drug Products: Cipro Injection [Link]
  22. FDA Approved Drug Products: Cipro Oral Suspension [Link]
  23. FDA Approved Drug Products: Cipro HC Suspension/Drops; Otic [Link]
  24. FDA Approved Drug Products: Cipro XR Extended Release Tablet [Link]
  25. FDA Approved Drug Products: Ciprodex Suspension/Drops; Otic [Link]
  26. FDA Approved Drug Products: Otiprio Injection [Link]
  27. Pfizer: Ciprofloxacin MSDS [Link]
Human Metabolome Database
HMDB0014677
KEGG Drug
D00186
KEGG Compound
C05349
PubChem Compound
2764
PubChem Substance
46504733
ChemSpider
2662
BindingDB
21690
RxNav
2551
ChEBI
100241
ChEMBL
CHEMBL8
ZINC
ZINC000000020220
Therapeutic Targets Database
DAP001360
PharmGKB
PA449009
PDBe Ligand
CPF
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ciprofloxacin
AHFS Codes
  • 52:04.04 — Antibacterials
  • 08:12.18 — Quinolones
PDB Entries
1oye / 1t9u / 2xct / 4bvv / 4kra / 5btc
FDA label
Download (120 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentExacerbation of Ulcerative Colitis / Granulomatous Colitis / Ulcerative Colitis, Active Severe1
4Active Not RecruitingTreatmentUlcerative Colitis1
4CompletedHealth Services ResearchAntibiotic Resistant Infection / Uncomplicated Urinary Tract Infections1
4CompletedOtherInfection1
4CompletedOtherQTc Prolongation, Hyperglycemia, Hypoglycemia1
4CompletedPreventionAdverse Reaction to Other Drugs and Medicines1
4CompletedPreventionBacteriuria / Urinary Tract Infection1
4CompletedPreventionBenign Prostatic Hyperplasia (BPH)1
4CompletedPreventionBK Virus Infection1
4CompletedPreventionMeningococcal Meningitis1

Pharmacoeconomics

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Dosage Forms
FormRouteStrength
SolutionConjunctival; Ophthalmic3 mg
Solution / dropsOphthalmic
Solution / dropsAuricular (otic)0.5 mg/0.25mL
Solution2 mg/ml
Solution / dropsAuricular (otic)0.25 mg/ml
SolutionIntravenous100 mg/50ml
Injection, solutionIntravenous400 mg/200ml
SolutionAuricular (otic)10 mg
Tablet, extended releaseOral1 g
Tablet, extended releaseOral500 mg
SuspensionOphthalmic3 mg
OintmentOphthalmic3 mg/1g
SolutionOphthalmic0.3 %
SolutionOphthalmic3.5 mg/1mL
OintmentOphthalmic3.5 mg/g
Solution / dropsOphthalmic3.5 mg/ml
OintmentOphthalmic0.3 %
Solution / dropsOphthalmic0.3 %
Solution / dropsOphthalmic0.3 %W/V
KitOral10 g/100mL
KitOral5 g/100mL
Solution, concentrateIntravenous10 mg/1mL
Solution, concentrateIntravenous2 mg/1mL
SuspensionAuricular (otic)
Tablet, film coatedOral1000 mg/1
SolutionIntravenous400 mg
Tablet, coatedOral750 mg
Tablet, film coatedOral100 MG
Tablet, film coatedOral250 MG
Tablet, film coatedOral500 MG
Tablet, film coatedOral750 MG
SolutionIntravenous200 mg/100ml
TabletOral250 mg
TabletOral750 mg
Suspension / dropsAuricular (otic)200 mg/100mL
LiquidIntravenous
SuspensionOral
Tablet, film coatedOral
Tablet, coatedOral100 mg
Solution200 mg/100mL
Solution400 mg/200 mL
Injection, solutionIntravenous2 mg/ml
Suspension / dropsAuricular (otic)
InjectionIntravenous
InjectionIntravenous10 mg/1mL
InjectionIntravenous2 mg/1mL
InjectionIntravenous200 mg/100mL
InjectionIntravenous200 mg/1
InjectionIntravenous400 mg/200mL
InjectionIntravenous400 mg/1
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous200 mg/100mL
Injection, solution, concentrateIntravenous10 mg/1mL
Injection, solution, concentrateIntravenous200 mg/20mL
Injection, solution, concentrateIntravenous400 mg/40mL
SolutionOphthalmic3 mg/1mL
Solution / dropsOphthalmic3 mg/1mL
Solution / dropsOphthalmic3.0 mg/1mL
Solution / dropsOphthalmic3.5 mg/1mL
Solution / dropsOphthalmic; Topical3 mg/1mL
Solution / dropsTopical3 mg/1mL
Solution / dropsTopical3.5 mg/1mL
SuspensionOral50 mg/1mL
TabletOral100 mg
TabletOral250 mg/1
TabletOral750 mg/1
Tablet, coatedOral250 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral750 mg/1
Tablet, film coated, extended releaseOral
Tablet, film coated, extended releaseOral1000 mg/1
Injection, solutionIntravenous2 mg/1mL
SolutionAuricular (otic)
SolutionParenteral2 mg/ml
TabletOral500 mg/1
Tablet, coatedOral500 mg/1
SolutionIntravenous
SolutionParenteral100 mg/50ml
SolutionParenteral200 mg/100ml
SolutionParenteral400 mg/200ml
SolutionOphthalmic3 mg
SolutionIntravenous200 mg
Injection, solutionParenteral100 MG/50ML
Injection, solutionParenteral200 MG/100ML
Injection, solutionParenteral400 MG/200ML
SolutionIntravenous100 mg
Tablet, coatedOral500 mg
Tablet, coatedOral250 mg
Injection, solutionParenteral2 MG/ML
Capsule500 mg
Injection, solution200 MG/100ML
Injection, solution400 MG/200ML
Powder, for suspensionOral250 MG/5ML
SuspensionOral100 ML
Tablet, coatedOral1000 MG
Injection, solutionIntravenous400 mg
SuspensionOral5 %
Tablet, extended releaseOral
Injection, solutionIntravenous0.2 %w/v
SolutionIntravenous2 mg
SuspensionConjunctival; Ophthalmic3 mg
Injection, solution100 MG/50ML
Tablet, film coatedOral
Solution / dropsAuricular (otic)3 mg/ml
Solution / dropsOphthalmic300 mg/100mL
SolutionAuricular (otic)1 mg
SuspensionIntratympanic6 mg/6mg
SuspensionIntratympanic6 mg/1mL
SuspensionAuricular (otic)3 mg
SolutionAuricular (otic)3 mg
Capsule250 mg
Capsule100 mg
Tablet, film coated, extended releaseOral500 mg/1
SolutionAuricular (otic); Ophthalmic3 mg
Injection, solutionIntravenous100 mg/50ml
SolutionOphthalmic
TabletOral500 mg
Solution / dropsAuricular (otic)0.3 %
Tablet, coated500 mg
TabletOral
SolutionIntravenous400 mg/200ml
Solution / dropsOphthalmic0.3 % w/v
Prices
Unit descriptionCostUnit
Cipro 400 mg Solution 40ml Vial259.99USD vial
Floxin Otic 0.3% Solution 10ml Bottle142.91USD bottle
Cipro 500 mg/5ml(10%) Suspension 100ml Bottle136.75USD bottle
Cipro HC 0.2-1% Suspension 10ml Bottle131.54USD bottle
Cipro 250 mg/5ml(5%) Suspension 100ml Bottle116.8USD bottle
Ocuflox 0.3% Solution 10ml Bottle106.09USD bottle
Ciprofloxacin HCl 0.3% Solution 10ml Bottle98.22USD bottle
Ciloxan 0.3% Ointment 3.5 gm Tube87.49USD tube
Floxin Otic 0.3% Solution 5ml Bottle86.49USD bottle
Ciloxan 0.3% Solution 5ml Bottle68.33USD bottle
Ocuflox 0.3% Solution 5ml Bottle57.32USD bottle
Ciprofloxacin HCl 0.3% Solution 5ml Bottle49.2USD bottle
ProQuin XR 3 500 mg 24 Hour tablet Disp Pack39.99USD disp
Ciprofloxacin HCl 0.3% Solution 2.5ml Bottle26.03USD bottle
Ciloxan 0.3% eye drops13.33USD ml
Ciprofloxacin 0.3% eye drop12.96USD ml
Cipro hc otic suspension12.65USD ml
Proquin xr 500 mg tablet12.18USD tablet
Cipro xr 1000 mg tablet11.91USD tablet
Ciprofloxacin-Ciproflox HCl 1000 mg 24 Hour tablet11.6USD tablet
Ocuflox 0.3% eye drops11.35USD ml
ProQuin XR 500 mg 24 Hour tablet11.18USD tablet
Ciprofloxacin er 1000 mg tablet11.16USD tablet
Cipro XR 500 mg 24 Hour tablet10.88USD tablet
Cipro XR 1000 mg 24 Hour tablet10.75USD tablet
Cipro xr 500 mg tablet10.46USD tablet
Ciprofloxacin-Ciproflox HCl 500 mg 24 Hour tablet10.19USD tablet
Ciprofloxacin er 500 mg tablet9.8USD tablet
Floxin 400 mg tablet9.55USD tablet
Cetraxal 0.2% ear solution7.14USD each
Floxin 200 mg tablet6.6USD tablet
Cipro 750 mg tablet6.26USD tablet
Cipro 500 mg tablet6.08USD tablet
Ciprofloxacin hcl 750 mg tablet5.65USD tablet
Floxin 300 mg tablet5.61USD tablet
Ciprofloxacin hcl 500 mg tablet5.59USD tablet
Cipro 250 mg tablet5.2USD tablet
Ciprofloxacin hcl 250 mg tablet4.59USD tablet
Floxin otic singles4.28USD each
Ciprofloxacin hcl 100 mg tablet4.17USD tablet
Ciloxan 0.3 % Solution2.18USD ml
Ciprofloxacin hcl powder1.29USD g
Apo-Ciproflox 0.3 % Solution1.18USD ml
Pms-Ciprofloxacin 0.3 % Solution1.18USD ml
Cipro i.v. 10 mg/ml vial0.72USD ml
Cipro i.v. 200 mg/100 ml d5w0.16USD ml
Ciprofloxacin 200 mg/20 ml vial0.13USD ml
Ciprofloxacn-d5w 200 mg/100 ml0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5286754No1994-02-152011-02-15US flag
CA2414271No2005-09-272021-06-13Canada flag
CA1330946No1994-07-262011-07-26Canada flag
US8187632Yes2012-05-292021-12-23US flag
US7709022Yes2010-05-042021-12-23US flag
US8846650No2014-09-302025-06-04US flag
US9149486No2015-10-062022-09-13US flag
US6359016No2002-03-192020-08-10US flag
US6284804No2001-09-042020-08-10US flag
US5972389No1999-10-262016-09-19US flag
US6340475No2002-01-222016-09-19US flag
US6635280No2003-10-212016-09-19US flag
US6488962No2002-12-032020-06-20US flag
US9205048No2015-12-082029-04-21US flag
US8318817No2012-11-272030-04-27US flag
US9220796No2015-12-292035-07-01US flag
US9233068No2016-01-122029-12-11US flag
US8932610No2015-01-132030-03-24US flag
US9345714No2016-05-242022-09-13US flag
US9402805No2016-08-022022-09-13US flag
US9603796No2017-03-282029-04-21US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)255-257 °Chttp://www.chemspider.com/Chemical-Structure.2662.html
water solubility<1mg/mLhttp://www.chemspider.com/Chemical-Structure.2662.html
logP0.28TAKACS-NOVAK,K ET AL. (1992)
pKa6.09TORNIANEN,K ET AL. (1996)
Predicted Properties
PropertyValueSource
Water Solubility1.35 mg/mLALOGPS
logP-0.57ALOGPS
logP-0.81ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.76ChemAxon
pKa (Strongest Basic)8.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.88 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.94 m3·mol-1ChemAxon
Polarizability33.12 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0029000000-1366c290ed86c001f05b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03dr-0069000000-a523751ea781088af897
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0009000000-f29d9954b2b055b62079
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01qi-0039000000-9cb66ef0790c686ea2b2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0089000000-c501b014ce11307842e1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0092000000-3f2bc2af8897693f406a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0290000000-97cd08c23e39dd2412ec
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0690000000-c683e1591a42526bd85d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0009000000-c8783567d83c0158dc21
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01qi-0049000000-0c3e1fd26ebdc13a760e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0079000000-84eeb4205e8a902133ec
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0192000000-3bebeb08e817739aa5f7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0290000000-40a5de8dd981d46dbe88
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0690000000-827770181ddec7977048
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03dr-0079000000-b9937740f37fc8a939a6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0009000000-06b6d10cecb7c9cab240
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0129000000-61453c8af95773ec6b29
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03dr-0296000000-de128c8d0e1eade700b6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0gx1-1292000000-2d8ff05ee839372800db
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-1290000000-f3446636040c80d0f8a3
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0090000000-6fc954ec7c93eaabef55
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001j-0198000000-0bfdea918825b34619d5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0090000000-5cee2f47095630088ff6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01p9-0095000000-c780444ec059d2f2f98e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01p9-0095000000-1dc83645e6c6c47ab02f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0920000000-9769fb468772887a192f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0397000000-0e08dc88a42e413750ce

Targets

Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
Gene Name
parC
Uniprot ID
P43702
Uniprot Name
DNA topoisomerase 4 subunit A
Molecular Weight
83366.24 Da
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:17139284]
  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:17016423]
  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:12473806]
  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:16034208]
  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:16517894]
  6. Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92. [PubMed:9293187]
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
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, inc...
Gene Name
gyrA
Uniprot ID
P43700
Uniprot Name
DNA gyrase subunit A
Molecular Weight
97817.145 Da
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:17139284]
  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:17016423]
  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:12473806]
  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:17378897]
  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:9056011]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Ubiquitin binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
Gene Name
TOP2A
Uniprot ID
P11388
Uniprot Name
DNA topoisomerase 2-alpha
Molecular Weight
174383.88 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  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:1323952]
  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:3015015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Keseru GM: Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods. Bioorg Med Chem Lett. 2003 Aug 18;13(16):2773-5. [PubMed:12873512]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
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, inc...
Gene Name
gyrA
Uniprot ID
P0AES4
Uniprot Name
DNA gyrase subunit A
Molecular Weight
96962.63 Da
References
  1. Hubschwerlen C, Specklin JL, Baeschlin DK, Borer Y, Haefeli S, Sigwalt C, Schroeder S, Locher HH: Structure-activity relationship in the oxazolidinone-quinolone hybrid series: influence of the central spacer on the antibacterial activity and the mode of action. Bioorg Med Chem Lett. 2003 Dec 1;13(23):4229-33. [PubMed:14623007]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
Gene Name
parC
Uniprot ID
P0C1U9
Uniprot Name
DNA topoisomerase 4 subunit A
Molecular Weight
91040.465 Da
References
  1. Wiles JA, Song Y, Wang Q, Lucien E, Hashimoto A, Cheng J, Marlor CW, Ou Y, Podos SD, Thanassi JA, Thoma CL, Deshpande M, Pucci MJ, Bradbury BJ: Biological evaluation of isothiazoloquinolones containing aromatic heterocycles at the 7-position: In vitro activity of a series of potent antibacterial agents that are effective against methicillin-resistant Staphylococcus aureus. Bioorg Med Chem Lett. 2006 Mar 1;16(5):1277-81. Epub 2005 Dec 7. [PubMed:16337789]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
Gene Name
parE
Uniprot ID
Q59192
Uniprot Name
DNA topoisomerase 4 subunit B
Molecular Weight
73006.17 Da
References
  1. Butler MM, Lamarr WA, Foster KA, Barnes MH, Skow DJ, Lyden PT, Kustigian LM, Zhi C, Brown NC, Wright GE, Bowlin TL: Antibacterial activity and mechanism of action of a novel anilinouracil-fluoroquinolone hybrid compound. Antimicrob Agents Chemother. 2007 Jan;51(1):119-27. Epub 2006 Oct 30. [PubMed:17074800]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
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, inc...
Gene Name
gyrA
Uniprot ID
P05653
Uniprot Name
DNA gyrase subunit A
Molecular Weight
92098.19 Da
References
  1. Butler MM, Lamarr WA, Foster KA, Barnes MH, Skow DJ, Lyden PT, Kustigian LM, Zhi C, Brown NC, Wright GE, Bowlin TL: Antibacterial activity and mechanism of action of a novel anilinouracil-fluoroquinolone hybrid compound. Antimicrob Agents Chemother. 2007 Jan;51(1):119-27. Epub 2006 Oct 30. [PubMed:17074800]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Drug transmembrane transporter activity
Specific Function
Multidrug efflux pump that functions probably as a Na(+)/drug antiporter.
Gene Name
mdtK
Uniprot ID
C3T8E2
Uniprot Name
Multidrug resistance protein MdtK
Molecular Weight
49446.52 Da
References
  1. Long F, Rouquette-Loughlin C, Shafer WM, Yu EW: Functional cloning and characterization of the multidrug efflux pumps NorM from Neisseria gonorrhoeae and YdhE from Escherichia coli. Antimicrob Agents Chemother. 2008 Sep;52(9):3052-60. doi: 10.1128/AAC.00475-08. Epub 2008 Jun 30. [PubMed:18591276]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
B4YQT9
Uniprot Name
Gyrase A
Molecular Weight
17024.015 Da
References
  1. Karkare S, Chung TT, Collin F, Mitchenall LA, McKay AR, Greive SJ, Meyer JJ, Lall N, Maxwell A: The naphthoquinone diospyrin is an inhibitor of DNA gyrase with a novel mechanism of action. J Biol Chem. 2013 Feb 15;288(7):5149-56. doi: 10.1074/jbc.M112.419069. Epub 2012 Dec 28. [PubMed:23275348]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
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, inc...
Gene Name
gyrA
Uniprot ID
P20831
Uniprot Name
DNA gyrase subunit A
Molecular Weight
99620.34 Da
References
  1. Surivet JP, Zumbrunn C, Rueedi G, Hubschwerlen C, Bur D, Bruyere T, Locher H, Ritz D, Keck W, Seiler P, Kohl C, Gauvin JC, Mirre A, Kaegi V, Dos Santos M, Gaertner M, Delers J, Enderlin-Paput M, Boehme M: Design, synthesis, and characterization of novel tetrahydropyran-based bacterial topoisomerase inhibitors with potent anti-gram-positive activity. J Med Chem. 2013 Sep 26;56(18):7396-415. doi: 10.1021/jm400963y. Epub 2013 Sep 11. [PubMed:23968485]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Batty KT, Davis TM, Ilett KF, Dusci LJ, Langton SR: The effect of ciprofloxacin on theophylline pharmacokinetics in healthy subjects. Br J Clin Pharmacol. 1995 Mar;39(3):305-11. [PubMed:7619673]
  2. Granfors MT, Backman JT, Neuvonen M, Neuvonen PJ: Ciprofloxacin greatly increases concentrations and hypotensive effect of tizanidine by inhibiting its cytochrome P450 1A2-mediated presystemic metabolism. Clin Pharmacol Ther. 2004 Dec;76(6):598-606. doi: 10.1016/j.clpt.2004.08.018. [PubMed:15592331]
  3. Zhang L, Wei MJ, Zhao CY, Qi HM: Determination of the inhibitory potential of 6 fluoroquinolones on CYP1A2 and CYP2C9 in human liver microsomes. Acta Pharmacol Sin. 2008 Dec;29(12):1507-14. doi: 10.1111/j.1745-7254.2008.00908.x. [PubMed:19026171]
  4. Flockhart Table of Drug Interactions [Link]
  5. Drug Interactions & Labeling - FDA [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. McLellan RA, Drobitch RK, Monshouwer M, Renton KW: Fluoroquinolone antibiotics inhibit cytochrome P450-mediated microsomal drug metabolism in rat and human. Drug Metab Dispos. 1996 Oct;24(10):1134-8. [PubMed:8894516]
  2. Flockhart Table of Drug Interactions [Link]
  3. Drug Interactions & Labeling - FDA [Link]
  4. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Flockhart Table of Drug Interactions [Link]
  2. Drug Interactions & Labeling - FDA [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
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 un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Flockhart Table of Drug Interactions [Link]
  2. Drug Interactions & Labeling - FDA [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Varshney A, Ansari Y, Zaidi N, Ahmad E, Badr G, Alam P, Khan RH: Analysis of binding interaction between antibacterial ciprofloxacin and human serum albumin by spectroscopic techniques. Cell Biochem Biophys. 2014 Sep;70(1):93-101. doi: 10.1007/s12013-014-9863-1. [PubMed:24913236]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
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:11743742]
  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:15032316]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
Data is limited to in vitro studies.
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [PubMed:17509534]
  2. Ohta KY, Imamura Y, Okudaira N, Atsumi R, Inoue K, Yuasa H: Functional characterization of multidrug and toxin extrusion protein 1 as a facilitative transporter for fluoroquinolones. J Pharmacol Exp Ther. 2009 Feb;328(2):628-34. doi: 10.1124/jpet.108.142257. Epub 2008 Nov 12. [PubMed:19004926]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data are based on an in vitro study.
General Function
Drug transmembrane transporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
Gene Name
SLC47A2
Uniprot ID
Q86VL8
Uniprot Name
Multidrug and toxin extrusion protein 2
Molecular Weight
65083.915 Da
References
  1. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [PubMed:17509534]

Drug created on June 13, 2005 07:24 / Updated on November 30, 2020 13:38

Drug search 4