Identification

Name
Ciprofloxacin
Accession Number
DB00537  (APRD00424, EXPT00999)
Type
Small Molecule
Groups
Approved, Investigational
Description

Ciprofloxacin is a broad-spectrum antimicrobial carboxyfluoroquinoline.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.

Structure
Thumb
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
  • Ciprofloxacine
  • Ciprofloxacino
  • Ciprofloxacinum
External IDs
BAY Q 3939 / BAY-Q-3939 / BAYQ3939 / J01MA02
Product Ingredients
IngredientUNIICASInChI Key
Ciprofloxacin hydrochloride0MP32MFP6C93107-08-5DIOIOSKKIYDRIQ-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act CiprofloxacinTablet750 mgOralTeva2004-02-18Not applicableCanada
Act CiprofloxacinTablet500 mgOralTeva2004-02-18Not applicableCanada
Act CiprofloxacinTablet250 mgOralTeva2004-02-18Not applicableCanada
CetraxalSolution / drops0.5 mg/0.25mLAuricular (otic)Wraser Llc2009-05-14Not applicableUs
CiloxanSolution / drops3 mg/1mLOphthalmicALCON LABORATORIES, INC.1991-01-15Not applicableUs
CiloxanSolution / drops3 mg/1mLOphthalmicRemedy Repack2018-05-30Not applicableUs
CiloxanOintment0.3 %OphthalmicNovartis1998-10-07Not applicableCanada
CiloxanSolution3.5 mg/1mLOphthalmicPhysicians Total Care, Inc.1995-07-10Not applicableUs
CiloxanOintment3 mg/1gOphthalmicALCON LABORATORIES, INC.1998-06-02Not applicableUs
CiloxanSolution0.3 %OphthalmicNovartis1992-12-31Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-ciprofloxTablet250 mgOralApotex Corporation2004-02-09Not applicableCanada
Apo-ciprofloxTablet750 mgOralApotex Corporation2004-02-09Not applicableCanada
Apo-ciprofloxSolution0.3 %OphthalmicApotex Corporation2005-09-14Not applicableCanada
Apo-ciprofloxTablet500 mgOralApotex Corporation2004-02-09Not applicableCanada
Auro-ciprofloxacinTablet750 mgOralAuro Pharma Inc2012-06-13Not applicableCanada
Auro-ciprofloxacinTablet250 mgOralAuro Pharma Inc2012-06-13Not applicableCanada
Auro-ciprofloxacinTablet500 mgOralAuro Pharma Inc2012-06-13Not applicableCanada
Bio-ciprofloxacinTablet500 mgOralBiomed Pharma2016-06-17Not applicableCanada
CiprofloxacinTablet, film coated500 mg/1OralWest Ward Pharmaceutical2004-06-09Not applicableUs
CiprofloxacinTablet, film coated500 mg/1OralWest-Ward Pharmaceuticals Corp2004-06-09Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
CiproCiprofloxacin hydrochloride (2 mg/1mL) + Benzyl alcohol (9 mg/1mL) + Hydrocortisone (10 mg/1mL)SuspensionAuricular (otic)Physicians Total Care, Inc.2009-02-12Not applicableUs
CiproCiprofloxacin (452.2 mg/1) + Ciprofloxacin hydrochloride (574.9 1/1)Tablet, film coated, extended releaseOralBayer2012-10-01Not applicableUs
CiproCiprofloxacin (212.6 mg/1) + Ciprofloxacin hydrochloride (287.5 1/1)Tablet, film coated, extended releaseOralBayer2012-10-01Not applicableUs
CiproCiprofloxacin (452.2 mg/1) + Ciprofloxacin hydrochloride (574.9 1/1)Tablet, film coated, extended releaseOralBayer2012-10-01Not applicableUs
CiproCiprofloxacin (212.6 mg/1) + Ciprofloxacin hydrochloride (287.5 1/1)Tablet, film coated, extended releaseOralBayer2012-10-01Not applicableUs
Cipro HCCiprofloxacin hydrochloride (2 mg/1mL) + Benzyl alcohol (9 mg/1mL) + Hydrocortisone (10 mg/1mL)SuspensionAuricular (otic)Stat Rx USA1998-02-10Not applicableUs
Cipro HCCiprofloxacin hydrochloride (2 mg/1mL) + Hydrocortisone (10 mg/1mL)SuspensionAuricular (otic)A-S Medication Solutions1999-03-15Not applicableUs
Cipro HCCiprofloxacin hydrochloride (2 mg/1mL) + Hydrocortisone (10 mg/1mL)SuspensionAuricular (otic)ALCON LABORATORIES, INC.1999-03-15Not applicableUs
Cipro HC Otic SuspensionCiprofloxacin (2 mg) + Hydrocortisone (10 mg)SuspensionAuricular (otic)Alcon, Inc.1999-06-222008-12-08Canada
Cipro XRCiprofloxacin hydrochloride (287.5 mg/1) + Ciprofloxacin (212.6 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2003-01-302011-06-30Us
International/Other Brands
Bacquinor / Baycip / Ciflox / Cifloxin / Ciprinol / Ciprobay / Ciprocinol / Ciprodar / Ciproxan / Ciproxin / Flociprin / Proquin
Categories
UNII
5E8K9I0O4U
CAS number
85721-33-1
Weight
Average: 331.3415
Monoisotopic: 331.133219662
Chemical Formula
C17H18FN3O3
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

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).

Associated Conditions
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.

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
Human
UPotassium voltage-gated channel subfamily H member 2Not AvailableHuman
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

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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Ciprofloxacin.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Ciprofloxacin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Ciprofloxacin.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Ciprofloxacin.
3,5-diiodothyropropionic acidCiprofloxacin can cause a decrease in the absorption of 3,5-diiodothyropropionic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Ciprofloxacin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Ciprofloxacin.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Ciprofloxacin.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Ciprofloxacin.
7,9-DimethylguanineThe serum concentration of 7,9-Dimethylguanine can be increased when it is combined with Ciprofloxacin.
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.

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. 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:8718602]
  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:8820479]
  4. Brouwers JR: Drug interactions with quinolone antibacterials. Drug Saf. 1992 Jul-Aug;7(4):268-81. [PubMed:1524699]
External Links
Human Metabolome Database
HMDB0014677
KEGG Drug
D00186
KEGG Compound
C05349
PubChem Compound
2764
PubChem Substance
46504733
ChemSpider
2662
BindingDB
21690
ChEBI
100241
ChEMBL
CHEMBL8
Therapeutic Targets Database
DAP001360
PharmGKB
PA449009
HET
CPF
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ciprofloxacin
ATC Codes
J01MA02 — CiprofloxacinJ01RA11 — Ciprofloxacin and tinidazoleS02AA15 — CiprofloxacinJ01RA12 — Ciprofloxacin and ornidazoleS01AE03 — CiprofloxacinS03AA07 — CiprofloxacinJ01RA10 — Ciprofloxacin and metronidazole
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
0CompletedTreatmentAlcoholic Cirrhosis / Alcoholic Hepatitis (AH)1
0Enrolling by InvitationBasic ScienceDietary Modifications / Nutrition1
0Not Yet RecruitingTreatmentRhinoscleroma1
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableBacterial Infections / Brain Injury1
1CompletedNot AvailableDysbacteriosis1
1CompletedNot AvailableHealthy Volunteers3
1CompletedNot AvailableMetabolic Detoxication, Phase I1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedOtherHealthy Volunteers / Non-Smokers1
1CompletedPreventionEscherichia Coli Infections1
1CompletedTreatmentBacillus Anthracis (Anthrax)1
1CompletedTreatmentBilateral Middle Ear Effusion Requiring Tympanostomy Tube Placement1
1CompletedTreatmentCystic Fibrosis (CF)2
1CompletedTreatmentHealthy Volunteers / Purpura, Thrombocytopaenic, Idiopathic / Purpura, Thrombocytopenic, Idiopathic1
1CompletedTreatmentHepatitis C Virus (HCV) Infection1
1CompletedTreatmentInfection NOS / Pulmonary Disease, Chronic Obstructive1
1CompletedTreatmentPseudomonas Infections1
1CompletedTreatmentPulmonary Disease, Chronic Obstructive2
1CompletedTreatmentPulmonary Diseases1
1CompletedTreatmentRespiratory System1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1RecruitingTreatmentConjunctivitis / Conjunctivitis, Bacterial1
1SuspendedTreatmentAnthrax1
1WithdrawnTreatmentHealthy Volunteers1
1WithdrawnTreatmentMalignant Lymphomas1
1, 2CompletedTreatmentEar Diseases / Otitis / Otitis Externa / Otorhinolaryngologic Diseases1
1, 2RecruitingTreatmentAcute Myelogenous Leukaemia (AML) / Leukemia Acute Myeloid Leukemia (AML) / Leukemias1
1, 2TerminatedTreatmentDiabetic Foot Ulcers (DFU)1
1, 2Unknown StatusPreventionHearing loss or impairment1
2Active Not RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL)1
2CompletedPreventionCrohn's Disease (CD)1
2CompletedPreventionCystic Fibrosis (CF) / Pulmonary Disease, Chronic Obstructive1
2CompletedTreatmentAcute Otitis Media / AOMT1
2CompletedTreatmentAcute Bacterial Corneal Ulcers / Bacterial Keratitis1
2CompletedTreatmentAnthrax1
2CompletedTreatmentBronchiectasis1
2CompletedTreatmentCarcinoma of Head/Neck / Squamous Cell Carcinoma (SCC)1
2CompletedTreatmentCritical Illness / Hospital Acquired Infections / Pneumonia / Pyrexia / Systemic Inflammatory Response Syndrome (SIRS)1
2CompletedTreatmentCystic Fibrosis (CF)1
2CompletedTreatmentEar Diseases / Otitis / Otitis Externa / Otorhinolaryngologic Diseases2
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
2CompletedTreatmentNon-Cystic Fibrosis Bronchiectasis1
2CompletedTreatmentOtitis Externa1
2CompletedTreatmentPyelonephritis / Urinary Tract Infections (UTIs)1
2CompletedTreatmentRheumatoid Arthritis1
2CompletedTreatmentUrinary Tract Infections (UTIs)1
2Not Yet RecruitingPreventionLeak, Anastomotic / Rectal Carcinoma1
2RecruitingPreventionProstate Infections1
2RecruitingTreatmentAdherent-invasive E. Coli / Crohn's Disease (CD)1
2RecruitingTreatmentCrohn's Disease (CD)3
2RecruitingTreatmentInfected Immature Permanent Teeth1
2TerminatedTreatmentAcute Otitis Media1
2TerminatedTreatmentCrohn's Disease (CD)1
2TerminatedTreatmentInfected Spacers / Prosthetic Joint Infections of Hip / Prosthetic Joint Infections of Knee1
2TerminatedTreatmentOsteomyelitis1
2Unknown StatusTreatmentPlague1
2WithdrawnDiagnosticProstate Cancer1
3Active Not RecruitingTreatmentBenign Lymphoepithelial Lesion / Human Immunodeficiency Virus (HIV) / Salivary Gland Diseases1
3Active Not RecruitingTreatmentTravelers' Diarrhea1
3CompletedNot AvailableAcute Otitis Media1
3CompletedPreventionBacterial Infections1
3CompletedSupportive CareInfection NOS / Multiple Myeloma (MM)1
3CompletedTreatmentAcute Otitis Externa1
3CompletedTreatmentAcute Otitis Externa / Swimmer's Ear1
3CompletedTreatmentAntibiotics / Chronic Obstructive Pulmonary Disease (COPD) / Sepsis1
3CompletedTreatmentBacterial Infections / Minor burns1
3CompletedTreatmentBronchiectasis1
3CompletedTreatmentCancer, Breast / Cyclophosphamide / Doxorubicin / High Risk / Positive Nodes1
3CompletedTreatmentCholera2
3CompletedTreatmentCrohn's Disease With Perianal Fistulas1
3CompletedTreatmentInfectious Diseases1
3CompletedTreatmentNeutropenia, Febrile1
3CompletedTreatmentOtitis Externa1
3CompletedTreatmentOtitis Media (OM)1
3CompletedTreatmentPneumonia1
3CompletedTreatmentUrinary Tract Infections (UTIs)2
3Not Yet RecruitingTreatmentChronic Rhinosinusitis (Diagnosis)1
3RecruitingTreatmentAntibiotic Resistant Infection / Complicated skin infection bacterial / Complicated Urinary Tract Infections / Urinary Tract Infections (UTIs)1
3RecruitingTreatmentAntibiotic Resistant Infection / Complicated skin infection bacterial / Intra Abdominal Infections1
3RecruitingTreatmentAntibiotic Resistant Infection / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs)1
3RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3RecruitingTreatmentEnterobacteriaceae Infections1
3RecruitingTreatmentKeratitis; Infectious Disease (Manifestation)1
3TerminatedPreventionMen Who Must Undergo a Prostate Biopsy Related to Prostate Cancer Suspicion1
3TerminatedPreventionUrolithiasis1
3TerminatedTreatmentAcute Otitis Externa1
3TerminatedTreatmentBladder Cancers1
3TerminatedTreatmentDiverticular Sigmoïditis1
3TerminatedTreatmentElevated Prostate Specific Antigen1
3TerminatedTreatmentFevers / Malignancies / Neutropenias1
3TerminatedTreatmentOtitis Externa1
3TerminatedTreatmentOtitis Media in Patients With Tympanostomy Tubes1
3Unknown StatusSupportive CareBrain and Central Nervous System Tumors / Malignant Lymphomas / Neutropenias / Psychosocial Effects of Cancer and Its Treatment / Small Intestine Cancer / Unspecified Adult Solid Tumor, Protocol Specific1
3Unknown StatusTreatmentAcute Otitis Externa1
3WithdrawnPreventionSpontaneous Bacterial Peritonitis (SBP)1
4Active Not RecruitingTreatmentAntibiotic Resistant Infection / UTI - Lower Urinary Tract Infection1
4Active Not RecruitingTreatmentInfection NOS1
4CompletedNot AvailablePregnancy1
4CompletedPreventionAdverse Reaction to Other Drugs and Medicines1
4CompletedPreventionBacteriuria / Urinary Tract Infections (UTIs)1
4CompletedPreventionBenign Prostatic Hyperplasia (BPH)1
4CompletedPreventionMeningococcal Meningitis1
4CompletedPreventionUrinary Tract Infections (UTIs)1
4CompletedSupportive CareCancer, Breast1
4CompletedTreatmentCataracts1
4CompletedTreatmentChlamydia Trachomatis / Human Immunodeficiency Virus (HIV) / Neisseria Gonorrhoeae Infection1
4CompletedTreatmentFevers / Urinary Tract Infections (UTIs)1
4CompletedTreatmentLiver Abscess, Pyogenic1
4CompletedTreatmentLiver Cirrhosis / SBP1
4CompletedTreatmentPeriodontitis, Chronic1
4CompletedTreatmentProstate Cancer1
4CompletedTreatmentPyelonephritis / Urinary Tract Infections (UTIs)1
4CompletedTreatmentUlcerative Colitis (UC)1
4CompletedTreatmentUncomplicated Bacterial Cystitis1
4CompletedTreatmentUrinary Tract Infections (UTIs)4
4Enrolling by InvitationTreatmentSmall Intestinal Bacterial Overgrowth1
4Not Yet RecruitingPreventionMeningococcal Meningitis1
4Not Yet RecruitingTreatmentOtitis Media (OM) / Otorrhoea1
4RecruitingHealth Services ResearchAntibiotic Resistant Infection / Uncomplicated Urinary Tract Infections1
4RecruitingOtherChronic Obstructive Pulmonary Disease (COPD) / Pseudomonas Aeruginosa / Respiratory Tract Infections (RTI)1
4RecruitingPreventionBK Virus Infection1
4RecruitingPreventionCalcium Nephrolithiasis / Ureteral Calculus / Ureteral Stones1
4RecruitingPreventionRenal Stones1
4RecruitingSupportive CarePancreatic Cystic Lesions1
4RecruitingTreatmentAsthma Bronchial1
4RecruitingTreatmentCritical Illness / Mechanical Ventilation Complication1
4RecruitingTreatmentEarly Stage Breast Cancer1
4RecruitingTreatmentUlcerative Colitis (UC)1
4SuspendedTreatmentGallstone formation1
4TerminatedDiagnosticProstate Infections1
4WithdrawnDiagnosticAscites / Infection NOS / Liver Cirrhosis1
4WithdrawnTreatmentOtitis Media With Effusion in Children / Otorrhoea1
Not AvailableActive Not RecruitingPreventionCatheter-Related Infections / Urinary Tract Infections (UTIs)1
Not AvailableActive Not RecruitingSupportive CareAscites (Non-Malignant) / Ascites Hepatic / Liver Cirrhosis1
Not AvailableCompletedNot AvailableAcute Cystitis1
Not AvailableCompletedNot AvailableBronchiectasis / Pulmonary Disease, Chronic Obstructive1
Not AvailableCompletedNot AvailableInfection NOS2
Not AvailableCompletedBasic ScienceEndotoxaemia1
Not AvailableCompletedBasic ScienceHealthy Volunteers / Sepsis1
Not AvailableCompletedPreventionPancreatic Cysts1
Not AvailableCompletedScreeningAntibiotic Resistance, Bacterial1
Not AvailableCompletedTreatmentAppendicitis / Children1
Not AvailableCompletedTreatmentCeftazidime / Ciprofloxacin / Pediatrics / Voriconazole1
Not AvailableCompletedTreatmentUlcerative Colitis (UC)1
Not AvailableCompletedTreatmentUrinary Tract Infections (UTIs)1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Epilepsies / Feeling Anxious / Flu caused by Influenza / Gastroparesis / Gynaecological infection / Headaches / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hospital-acquired bacterial pneumonia / Hyperlipidemias / Infantile Hemangiomas / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Migraines / Muscle Spasms / Nausea / Opioid Addiction / Pain NOS / Plague / Pneumonia / Prophylaxis / Psittacosis / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombotic events / Toxic effect of hydrocyanic acid and cyanides / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
Not AvailableRecruitingNot AvailableCystitis / Pyelonephritis / Cystic Fibrosis / Anthrax1
Not AvailableRecruitingDiagnosticGonococcal infections / Gonorrhoea1
Not AvailableRecruitingPreventionMotility Disorders / Staphylococcus Aureus1
Not AvailableRecruitingPreventionUrolithiasis / UTI1
Not AvailableRecruitingTreatmentBronchiectasis1
Not AvailableRecruitingTreatmentProsthetic Joint Infection1
Not AvailableTerminatedSupportive CareChronic Myeloproliferative Disorders / Fever, Sweats, and Hot Flashes / Infection NOS / Leukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms / Neutropenias / Precancerous Conditions / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableTerminatedTreatmentClostridium Difficile / Prostate Cancer / Urinary Tract Infections (UTIs)1
Not AvailableTerminatedTreatmentHealthy Volunteers1
Not AvailableUnknown StatusTreatmentDiabetic Foot / Diabetic Foot Ulcers (DFU) / Osteomyelitis1
Not AvailableUnknown StatusTreatmentPeritonitis1

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
  • ACS Dobfar SPA
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Akorn Inc.
  • Alcon Laboratories
  • Allergan Inc.
  • Amerisource Health Services Corp.
  • Anchen Pharmaceuticals Inc.
  • Apotex Inc.
  • Apotheca Inc.
  • AQ Pharmaceuticals Inc.
  • Arrow Pharm Malta Ltd.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Barr Pharmaceuticals
  • Bausch & Lomb Inc.
  • Baxter International Inc.
  • Bayer Healthcare
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Blenheim Pharmacal
  • Blu Pharmaceuticals LLC
  • Bryant Ranch Prepack
  • Cardinal Health
  • Carlsbad Technology Inc.
  • Claris Lifesciences Inc.
  • Cobalt Pharmaceuticals Inc.
  • Comprehensive Consultant Services Inc.
  • Core Pharmaceuticals
  • Daiichi Sankyo
  • Depomed Inc.
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Dorx LLC
  • Esprit Pharma Inc.
  • Falcon Pharmaceuticals Ltd.
  • Forum Products Inc.
  • Golden State Medical Supply Inc.
  • Goldline Laboratories Inc.
  • H.J. Harkins Co. Inc.
  • Hi Tech Pharmacal Co. Inc.
  • Hikma Pharmaceuticals
  • Hospira Inc.
  • Indoco Remedies Limited
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • J.B. Chemicals & Pharmaceuticals
  • Kaiser Foundation Hospital
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Dosage forms
FormRouteStrength
OintmentOphthalmic0.3 %
OintmentOphthalmic3 mg/1g
SolutionOphthalmic3.5 mg/1mL
Kit10 g/100mL
Kit5 g/100mL
Solution, concentrateIntravenous10 mg/1mL
Solution, concentrateIntravenous2 mg/1mL
Tablet, film coatedOral1000 mg/1
SuspensionAuricular (otic)
LiquidIntravenous10 mg
SuspensionOral500 mg
TabletOral100 mg
Tablet, extended releaseOral1000 mg
Tablet, extended releaseOral500 mg
Tablet, film coatedOral
Suspension / dropsAuricular (otic)
InjectionIntravenous10 mg/1mL
InjectionIntravenous2 mg/1mL
InjectionIntravenous200 mg/100mL
InjectionIntravenous200 mg/1
InjectionIntravenous400 mg/1
InjectionIntravenous400 mg/200mL
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous2 mg/1mL
Injection, solutionIntravenous200 mg/100mL
Injection, solution, concentrateIntravenous10 mg/1mL
Injection, solution, concentrateIntravenous200 mg/20mL
Injection, solution, concentrateIntravenous400 mg/40mL
Kit250 mg/5mL
Kit500 mg/5mL
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
Solution / dropsTopical3.5 mg/1
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
Tablet, film coated, extended releaseOral500 mg/1
SolutionOphthalmic3 mg/1mL
TabletOral500 mg/1
Tablet, coatedOral500 mg/1
SolutionIntravenous0.2 %
SolutionIntravenous10 mg
SolutionIntravenous2.0 mg
SolutionIntravenous2 mg
Solution / dropsAuricular (otic)0.5 mg/0.25mL
SuspensionIntratympanic6 mg/1mL
SuspensionIntratympanic6 mg/6mg
SolutionAuricular (otic)
For solutionAuricular (otic)
Tablet, film coated, extended releaseOral500 mg/1
SolutionOphthalmic0.3 %
TabletOral250 mg
TabletOral500 mg
TabletOral750 mg
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)
US5286754No1994-02-152011-02-15Us
CA2414271No2005-09-272021-06-13Canada
CA1330946No1994-07-262011-07-26Canada
US8187632Yes2012-05-292021-12-23Us
US7709022Yes2010-05-042021-12-23Us
US8846650No2014-09-302025-06-04Us
US9149486No2015-10-062022-09-13Us
US6359016No2002-03-192020-08-10Us
US6284804No2001-09-042020-08-10Us
US5972389No1999-10-262016-09-19Us
US6340475No2002-01-222016-09-19Us
US6635280No2003-10-212016-09-19Us
US6488962No2002-12-032020-06-20Us
US9205048No2015-12-082029-04-21Us
US8318817No2012-11-272030-04-27Us
US9220796No2015-12-292035-07-01Us
US9233068No2016-01-122029-12-11Us
US8932610No2015-01-132030-03-24Us
US9345714No2016-05-242022-09-13Us
US9402805No2016-08-022022-09-13Us
US9603796No2017-03-282029-04-21Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)255-257 °CNot Available
water solubility3E+004 mg/L (at 20 °C)NOWARA,A ET AL. (1997)
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

Taxonomy

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
Quinoline-3-carboxylic acid / Fluoroquinolone / N-arylpiperazine / Aminoquinoline / Haloquinoline / Dihydroquinolone / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives / Tertiary aliphatic/aromatic amine
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-arylpiperazine, aminoquinoline, quinolone antibiotic, fluoroquinolone antibiotic, quinolone, quinolinemonocarboxylic acid (CHEBI:100241)

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
Human
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
Human
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
Human
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. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  3. Drug Interactions & Labeling - FDA [Link]
Kind
Protein
Organism
Human
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  2. Drug Interactions & Labeling - FDA [Link]
Kind
Protein
Organism
Human
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  2. Drug Interactions & Labeling - FDA [Link]
Kind
Protein
Organism
Human
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. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  4. Drug Interactions & Labeling - FDA [Link]

Transporters

Kind
Protein
Organism
Human
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
Human
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
Human
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 18, 2018 13:31