Ciprofloxacin

Identification

Summary

Ciprofloxacin is a second generation fluoroquinolone used to treat various susceptible bacterial infections.

Brand Names

Cetraxal, Ciloxan, Cipro, Cipro HC, Ciprodex, Ciprofloxacin, Otiprio, Otixal, Otovel, Proquin

Generic Name

Ciprofloxacin

DrugBank Accession Number

DB00537

Background

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

Similar Structures

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

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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

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Dose Form
Used in combination to treat	Acute otitis externa	Combination Product in combination with: Dexamethasone (DB01234)	••••••••••••		•••••••• • •••••
Used in combination to treat	Acute otitis externa	Combination Product in combination with: Dexamethasone (DB01234)	••••••••••••		•••••••••• • •••••
Treatment of	Acute otitis externa caused by pseudomonas aeruginosa		••••••••••••		••••••••
Used in combination to treat	Acute otitis media	Combination Product in combination with: Dexamethasone (DB01234)	••••••••••••		•••••••••• • •••••
Treatment of	Acute sinusitis		••••••••••••	•••••

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

Target	Actions	Organism
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 2	Not Available	Humans
UDNA gyrase subunit A	Not Available	Escherichia coli (strain K12)
UDNA topoisomerase 4 subunit A	Not Available	Staphylococcus aureus
UDNA topoisomerase 4 subunit B	Not Available	Bacillus subtilis (strain 168)
UDNA gyrase subunit A	Not Available	Bacillus subtilis (strain 168)
UMultidrug resistance protein MdtK	Not Available	Escherichia coli
UGyrase A	Not Available	Mycobacterium tuberculosis
UDNA gyrase subunit A	Not Available	Staphylococcus 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

Ciprofloxacin

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}

Pathways

Not Available

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Interactions

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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.

Drug	Interaction
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1,2-Benzodiazepine	The metabolism of 1,2-Benzodiazepine can be decreased when combined with Ciprofloxacin.
Abacavir	Ciprofloxacin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Ciprofloxacin.
Abiraterone	The metabolism of Abiraterone can be decreased when combined with Ciprofloxacin.
Acalabrutinib	The metabolism of Acalabrutinib can be decreased when combined with Ciprofloxacin.

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

Ingredient	UNII	CAS	InChI Key
Ciprofloxacin hydrochloride	4BA73M5E37	86393-32-0	ARPUHYJMCVWYCZ-UHFFFAOYSA-N
Ciprofloxacin lactate	UEY6XFC224	96186-80-0	NRBJWZSFNGZBFQ-UHFFFAOYSA-N

Product Images

International/Other Brands

Bacquinor / Baycip / Ciflox / Cifloxin / Ciprinol / Ciprobay / Ciprocinol / Ciprodar / Ciproxan / Ciproxin / Flociprin / Proquin

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Act Ciprofloxacin	Tablet	750 mg	Oral	TEVA Canada Limited	2004-02-18	Not applicable
Act Ciprofloxacin	Tablet	500 mg	Oral	TEVA Canada Limited	2004-02-18	Not applicable
Act Ciprofloxacin	Tablet	250 mg	Oral	TEVA Canada Limited	2004-02-18	Not applicable
Cetraxal	Solution / drops	0.5 mg/0.25mL	Auricular (otic)	Wraser Llc	2009-05-14	Not applicable
Ciloxan	Ointment	0.3 % w/w	Ophthalmic	Novartis	1998-10-07	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ag-ciprofloxacin	Tablet	500 mg	Oral	Angita Pharma Inc.	2020-01-20	Not applicable
Ag-ciprofloxacin	Tablet	250 mg	Oral	Angita Pharma Inc.	Not applicable	Not applicable
Ag-ciprofloxacin	Tablet	750 mg	Oral	Angita Pharma Inc.	Not applicable	Not applicable
Apo-ciproflox	Tablet	250 mg	Oral	Apotex Corporation	2004-02-09	Not applicable
Apo-ciproflox	Tablet	750 mg	Oral	Apotex Corporation	2004-02-09	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
ACEOTO PLUS®	Ciprofloxacin hydrochloride (3 mg) + Fluocinolone acetonide (0.25 mg)	Solution	Auricular (otic)	LABORATORIOS SALVAT S.A	2013-11-25	Not applicable
CETRAXAL PLUS EAR DROPS SOLUTION	Ciprofloxacin hydrochloride (3 mg) + Fluocinolone acetonide (0.25 mg)	Solution	Auricular (otic)	HYPHENS PHARMA PTE. LTD.	2014-08-29	Not applicable
CEXIDAL	Ciprofloxacin (3 MG/ML) + Fluocinolone acetonide (0.25 MG/ML)	Solution / drops	Auricular (otic)	Infectopharm Arzneimittel Und Consilium Gmbh	2014-07-08	Not applicable
CILODEX OTIC SUSPENSION	Ciprofloxacin hydrochloride (0.3 %) + Dexamethasone (0.1 %)	Solution	Auricular (otic)	NOVARTIS (SINGAPORE) PTE LTD	2006-04-18	Not applicable
Cipro	Ciprofloxacin (212.6 mg/1) + Ciprofloxacin hydrochloride (287.5 1/1)	Tablet, film coated, extended release	Oral	Bayer HealthCare Pharmaceuticals Inc.	2012-10-01	2016-07-27

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
CIPRONATIN 500 MG TABLET, 14 ADET	Ciprofloxacin (500 mg)	Tablet	Oral	ATABAY KİMYA SAN. VE TİC. A.Ş.	2013-01-29	Not applicable
CIPRONATIN 750 MG TABLET, 14 ADET	Ciprofloxacin (750 mg)	Tablet	Oral	ATABAY KİMYA SAN. VE TİC. A.Ş.	2013-01-29	Not applicable
CIPROXIN 400 MG FLAKON, 1 ADET	Ciprofloxacin (400 mg)	Injection, solution	Intravenous	BAYER TÜRK KİMYA SAN. LTD. ŞTİ.	2018-02-20	2024-01-23

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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
Takács-Novák K, Józan M, Szász H: Lipophilicity of antibacterial fluoroquinolones International Journal of Pharmaceutics. 1992 Feb 1;79(1-3):89-96. [Article]
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. [Article]
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. [Article]
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. [Article]
LeBel M: Ciprofloxacin: chemistry, mechanism of action, resistance, antimicrobial spectrum, pharmacokinetics, clinical trials, and adverse reactions. Pharmacotherapy. 1988;8(1):3-33. [Article]
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. [Article]
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. [Article]
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. [Article]
George MJ, Dew RB 3rd, Daly JS: Acute renal failure after an overdose of ciprofloxacin. Arch Intern Med. 1991 Mar;151(3):620. [Article]
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. [Article]
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. [Article]
FDA Approved Drug Products: Cipro [Link]
FDA Approved Drug Products: Cetraxal Solution/Drops;Otic [Link]
FDA Approved Drug Products: Ciloxan Solution/Drops; Opthmalmic [Link]
FDA Approved Drug Products: Ciloxan Ointment; Opthalmic [Link]
FDA Approved Drug Products: CIPRO IV (ciprofloxacin) injection [Link]
FDA Approved Drug Products: CIPRO (ciprofloxacin) oral tablets and suspension [Link]
FDA Approved Drug Products: Cipro HC Suspension/Drops; Otic [Link]
FDA Approved Drug Products: CIPRO XR (ciprofloxacin) extended-release tablets [Link]
FDA Approved Drug Products: Ciprodex Suspension/Drops; Otic [Link]
FDA Approved Drug Products: Otiprio Injection [Link]
Pfizer: Ciprofloxacin MSDS [Link]
FDA Approved Drug Products: OTOVEL (ciprofloxacin and fluocinolone acetonide) otic solution [Link]

External Links

Human Metabolome Database: HMDB0014677
KEGG Drug: D00186
KEGG Compound: C05349
PubChem Compound: 2764
PubChem Substance: 46504733
ChemSpider: 2662
BindingDB: 21690
RxNav: 2551
ChEBI: 192484
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

PDB Entries

1oye / 1t9u / 2xct / 4bvv / 4kra / 5btc / 8gjl

FDA label

Download (120 KB)

MSDS

Download (73.9 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Health Services Research	Antibiotic Resistant Infection / Uncomplicated Urinary Tract Infections	1
4	Completed	Other	Infection	1
4	Completed	Other	QTc Prolongation, Hyperglycemia, Hypoglycemia	1
4	Completed	Prevention	Adverse Reaction to Other Drugs and Medicines	1
4	Completed	Prevention	Bacteriuria / Urinary Tract Infection	1

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
Keltman Pharmaceuticals Inc.
Kenyon Drug Co.
Lake Erie Medical and Surgical Supply
Lannett Co. Inc.
Legacy Pharmaceuticals Packaging LLC
Liberty Pharmaceuticals
Major Pharmaceuticals
Matrix Laboratories Ltd.
Mckesson Corp.
Medisca Inc.
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Neuman Distributors Inc.
Nexus Pharmaceuticals
Northstar Rx LLC
Novartis AG
Novex Pharma
Nucare Pharmaceuticals Inc.
Pack Pharmaceuticals
Palmetto Pharmaceuticals Inc.
Par Pharmaceuticals
PCA LLC
PD-Rx Pharmaceuticals Inc.
Pfizer Inc.
Pharmaceutical Utilization Management Program VA Inc.
Pharmaforce Inc.
Pharmedix
Pharmpak Inc.
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Prescript Pharmaceuticals
Prescription Dispensing Service Inc.
Ranbaxy Laboratories
Rebel Distributors Corp.
Redpharm Drug
Remedy Repack
Sagent Pharmaceuticals
Sandhills Packaging Inc.
Sandoz
Schering Corp.
Southwood Pharmaceuticals
St Mary's Medical Park Pharmacy
Stat Rx Usa
Stat Scripts LLC
Taro Pharmaceuticals USA
Testpak Holding Company Inc.
Teva Pharmaceutical Industries Ltd.
Tya Pharmaceuticals
UDL Laboratories
West-Ward Pharmaceuticals
WraSer Pharmaceuticals
Yung Shin Pharmaceutical Industry Ltd.

Dosage Forms

Form	Route	Strength
Solution / drops	Ophthalmic
Solution		2 mg/1ml
Tablet, film coated	Oral	555 mg
Tablet	Oral	250.000 mg
Solution	Intravenous	200.000 mg
Solution / drops	Auricular (otic)	0.5 mg/0.25mL
Solution
Solution	Auricular (otic)	2 mg
Solution	Auricular (otic)	3 mg
Solution / drops	Auricular (otic)
Tablet	Oral	250.0 mg
Solution	Intravenous	100 mg/50ml
Tablet, coated	Oral
Solution	Auricular (otic)	10 mg
Solution	Ophthalmic	3 mg
Solution	Auricular (otic)	0.3 %
Ointment	Ophthalmic	0.3 % w/w
Ointment	Ophthalmic	3 mg/1g
Solution	Ophthalmic	0.3 % w/v
Solution	Ophthalmic	3.5 mg/1mL
Ointment	Ophthalmic	3.5 mg/g
Solution / drops	Ophthalmic	3.5 mg/ml
Ointment	Ophthalmic	0.3 %
Solution / drops	Ophthalmic	0.3 %
Solution	Auricular (otic); Ophthalmic	3 mg/mL
Ointment	Ophthalmic	3 mg/g
Solution	Parenteral
Solution	Ophthalmic	3.5 mg/ml
Kit	Oral	10 g/100mL
Kit	Oral	5 g/100mL
Kit; suspension	Oral	10 g/100mL
Kit; suspension	Oral	5 g/100mL
Solution, concentrate	Intravenous	10 mg/1mL
Solution, concentrate	Intravenous	2 mg/1mL
Suspension	Auricular (otic)
Tablet, film coated	Oral	1000 mg/1
Solution	Intravenous	400 mg
Solution	Intravenous	40000000 mg
Tablet, coated	Oral	750 mg
Tablet, film coated	Oral	100 MG
Solution	Intravenous	200 mg/100ml
Liquid	Intravenous	10 mg / mL
Suspension	Oral	500 mg / 5 mL
Suspension	Oral	5 g
Tablet	Oral	100 mg / tab
Tablet	Oral	250 mg / tab
Tablet	Oral	500 mg / tab
Tablet, multilayer, extended release	Oral	1000 mg
Tablet, multilayer, extended release	Oral	500 mg
Tablet, film coated	Oral
Tablet, film coated	Oral	250.0 mg
Tablet, film coated	Oral	500.0 mg
Solution	Ophthalmic	3.000 mg
Tablet, film coated	Oral	291.0 MG
Tablet, film coated	Oral	582.0 MG
Solution	Auricular (otic)	0.2 %
Injection, solution	Intravenous	400 mg/200ml
Tablet, coated	Oral	500 mg
Suspension / drops	Auricular (otic)
Ointment	Conjunctival; Ophthalmic
Solution	Parenteral	100 mg
Tablet	Oral	1164.400 mg
Injection	Intravenous
Injection	Intravenous	10 mg/1mL
Injection	Intravenous	2 mg/1mL
Injection	Intravenous	200 mg/1
Injection	Intravenous	200 mg/100mL
Injection	Intravenous	400 mg/1
Injection	Intravenous	400 mg/200mL
Injection, solution	Intravenous	10 mg/1mL
Injection, solution	Intravenous	200 mg/100mL
Injection, solution, concentrate	Intravenous	10 mg/1mL
Injection, solution, concentrate	Intravenous	200 mg/20mL
Injection, solution, concentrate	Intravenous	400 mg/40mL
Kit; powder, for suspension	Oral	250 mg/5mL
Kit; powder, for suspension	Oral	500 mg/5mL
Solution	Ophthalmic	3 mg/1mL
Solution / drops	Ophthalmic	3 mg/1mL
Solution / drops	Ophthalmic	3.0 mg/1mL
Solution / drops	Ophthalmic	3.5 mg/1mL
Solution / drops	Ophthalmic; Topical	3 mg/1mL
Solution / drops	Topical	3.5 mg/1mL
Tablet	Oral	250 mg/1
Tablet	Oral	750 mg/1
Tablet, coated	Oral	250 mg/1
Tablet, film coated	Oral	100 mg/1
Tablet, film coated	Oral	250 mg/1
Tablet, film coated	Oral	500 mg/1
Tablet, film coated	Oral	750 mg/1
Tablet, film coated, extended release	Oral
Tablet, film coated, extended release	Oral	1000 mg/1
Injection, solution	Intravenous	2 mg/1mL
Solution	Auricular (otic)
Tablet, film coated	Oral	582 MG
Solution	Parenteral
Tablet	Oral	500 mg/1
Tablet, coated	Oral	500 mg/1
Tablet, film coated	Oral	583 MG
Solution	Intravenous	0.2 %
Solution	Intravenous	10 mg / mL
Solution	Intravenous	2 mg/1ml
Solution	Intravenous	2 mg / mL
Solution	Intravenous	100 mg
Injection	Parenteral	0.1 g
Solution	Intravenous	2 mg
Solution	Parenteral	200000 mg
Solution	Parenteral	200 mg
Solution	Intravenous	20000000 mg
Solution	Intravenous	200 mg
Injection, solution	Intravenous
Injection, solution	Parenteral	100 MG/50ML
Injection, solution	Parenteral	200 MG/100ML
Injection, solution	Parenteral	400 MG/200ML
Injection, solution
Solution	Intravenous	10000000 mg
Solution	Intravenous	10 mg
Tablet, coated	Oral	50000000 mg
Injection, solution	Intravenous	2 mg/ml
Injection, solution	Parenteral	2 MG/ML
Injection	Intravenous	254.4 mg/100ml
Injection, solution		200 MG/100ML
Injection, solution		400 MG/200ML
Injection, solution	Intravenous	100 mg/50ml
Powder, for suspension	Oral	250 MG/5ML
Suspension	Oral	10 %
Tablet, coated	Oral	1000 MG
Injection, solution	Intravenous	400 mg
Suspension	Oral
Tablet, extended release	Oral
Suspension	Oral	5.000 g
Tablet	Oral	500.000 mg
Injection	Intravenous	2 mg/ml
Suspension	Conjunctival; Ophthalmic
Tablet, film coated	Oral
Solution / drops
Injection, solution		100 MG/50ML
Tablet	Oral	250.00 mg
Tablet	Oral	589.17 mg
Solution	Auricular (otic)	3.000 mg
Solution / drops	Conjunctival
Solution	Conjunctival; Ophthalmic	3 mg
Tablet	Oral
Tablet, extended release	Oral	1000 mg
Tablet, extended release	Oral	500 mg
Solution	Parenteral	0.2 g
Solution	Parenteral	0.4 g
Solution	Ophthalmic	3.0 mg/ml
Tablet	Oral	500.00 mg
Tablet	Oral	100 mg
Tablet	Oral	250 mg
Tablet	Oral	750 mg
Ointment	Ophthalmic
Solution / drops	Auricular (otic)
Solution	Auricular (otic)	1 mg
Suspension	Auricular (otic); Intratympanic	60 mg/1mL
Suspension	Intratympanic	6 mg/6mg
Suspension	Intratympanic	60 mg/1mL
Solution	Auricular (otic)	3 mg
Tablet, film coated, extended release	Oral	500 mg/1
Tablet	Oral	500.0000 mg
Tablet, coated	Oral	250 mg
Solution	Auricular (otic); Ophthalmic	3 mg
Solution	Ophthalmic	0.3 %
Solution / drops	Auricular (otic)	0.3 %
Tablet, coated
Suspension	Ophthalmic
Solution	Ophthalmic
Ointment	Ophthalmic
Ointment	Ophthalmic	3.00 mg
Solution	Intravenous	2 mg/ml
Injection, powder, for solution	Intramuscular	200 mg/100mL
Solution	Intravenous	400 mg/200ml
Tablet	Oral
Tablet, film coated	Oral	750 mg
Tablet, film coated	Oral	250 mg
Tablet	Oral	500 mg
Tablet, film coated	Oral	500 mg
Capsule		500 mg

Prices

Unit description	Cost	Unit
Cipro 400 mg Solution 40ml Vial	259.99USD	vial
Floxin Otic 0.3% Solution 10ml Bottle	142.91USD	bottle
Cipro 500 mg/5ml(10%) Suspension 100ml Bottle	136.75USD	bottle
Cipro HC 0.2-1% Suspension 10ml Bottle	131.54USD	bottle
Cipro 250 mg/5ml(5%) Suspension 100ml Bottle	116.8USD	bottle
Ocuflox 0.3% Solution 10ml Bottle	106.09USD	bottle
Ciprofloxacin HCl 0.3% Solution 10ml Bottle	98.22USD	bottle
Ciloxan 0.3% Ointment 3.5 gm Tube	87.49USD	tube
Floxin Otic 0.3% Solution 5ml Bottle	86.49USD	bottle
Ciloxan 0.3% Solution 5ml Bottle	68.33USD	bottle
Ocuflox 0.3% Solution 5ml Bottle	57.32USD	bottle
Ciprofloxacin HCl 0.3% Solution 5ml Bottle	49.2USD	bottle
ProQuin XR 3 500 mg 24 Hour tablet Disp Pack	39.99USD	disp
Ciprofloxacin HCl 0.3% Solution 2.5ml Bottle	26.03USD	bottle
Ciloxan 0.3% eye drops	13.33USD	ml
Ciprofloxacin 0.3% eye drop	12.96USD	ml
Cipro hc otic suspension	12.65USD	ml
Proquin xr 500 mg tablet	12.18USD	tablet
Cipro xr 1000 mg tablet	11.91USD	tablet
Ciprofloxacin-Ciproflox HCl 1000 mg 24 Hour tablet	11.6USD	tablet
Ocuflox 0.3% eye drops	11.35USD	ml
ProQuin XR 500 mg 24 Hour tablet	11.18USD	tablet
Ciprofloxacin er 1000 mg tablet	11.16USD	tablet
Cipro XR 500 mg 24 Hour tablet	10.88USD	tablet
Cipro XR 1000 mg 24 Hour tablet	10.75USD	tablet
Cipro xr 500 mg tablet	10.46USD	tablet
Ciprofloxacin-Ciproflox HCl 500 mg 24 Hour tablet	10.19USD	tablet
Ciprofloxacin er 500 mg tablet	9.8USD	tablet
Floxin 400 mg tablet	9.55USD	tablet
Cetraxal 0.2% ear solution	7.14USD	each
Floxin 200 mg tablet	6.6USD	tablet
Cipro 750 mg tablet	6.26USD	tablet
Cipro 500 mg tablet	6.08USD	tablet
Ciprofloxacin hcl 750 mg tablet	5.65USD	tablet
Floxin 300 mg tablet	5.61USD	tablet
Ciprofloxacin hcl 500 mg tablet	5.59USD	tablet
Cipro 250 mg tablet	5.2USD	tablet
Ciprofloxacin hcl 250 mg tablet	4.59USD	tablet
Floxin otic singles	4.28USD	each
Ciprofloxacin hcl 100 mg tablet	4.17USD	tablet
Ciloxan 0.3 % Solution	2.18USD	ml
Ciprofloxacin hcl powder	1.29USD	g
Apo-Ciproflox 0.3 % Solution	1.18USD	ml
Pms-Ciprofloxacin 0.3 % Solution	1.18USD	ml
Cipro i.v. 10 mg/ml vial	0.72USD	ml
Cipro i.v. 200 mg/100 ml d5w	0.16USD	ml
Ciprofloxacin 200 mg/20 ml vial	0.13USD	ml
Ciprofloxacn-d5w 200 mg/100 ml	0.03USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5286754	No	1994-02-15	2011-02-15
CA2414271	No	2005-09-27	2021-06-13
CA1330946	No	1994-07-26	2011-07-26
US8187632	Yes	2012-05-29	2021-12-23
US7709022	Yes	2010-05-04	2021-12-23
US8846650	No	2014-09-30	2025-06-04
US9149486	No	2015-10-06	2022-09-13
US6359016	No	2002-03-19	2020-08-10
US6284804	No	2001-09-04	2020-08-10
US5972389	No	1999-10-26	2016-09-19
US6340475	No	2002-01-22	2016-09-19
US6635280	No	2003-10-21	2016-09-19
US6488962	No	2002-12-03	2020-06-20
US9205048	No	2015-12-08	2029-04-21
US8318817	No	2012-11-27	2030-04-27
US9220796	No	2015-12-29	2035-07-01
US9233068	No	2016-01-12	2029-12-11
US8932610	No	2015-01-13	2030-03-24
US9345714	No	2016-05-24	2022-09-13
US9402805	No	2016-08-02	2022-09-13
US9603796	No	2017-03-28	2029-04-21
US11040004	No	2021-06-22	2037-11-12
US11246863	No	2018-11-27	2038-11-27
US11369566	No	2009-04-21	2029-04-21

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	255-257 °C	http://www.chemspider.com/Chemical-Structure.2662.html
water solubility	<1mg/mL	http://www.chemspider.com/Chemical-Structure.2662.html
logP	0.28	TAKACS-NOVAK,K ET AL. (1992)
pKa	6.09	TORNIANEN,K ET AL. (1996)

Predicted Properties

Property	Value	Source
Water Solubility	1.35 mg/mL	ALOGPS
logP	-0.57	ALOGPS
logP	-0.86	Chemaxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	5.56	Chemaxon
pKa (Strongest Basic)	8.77	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	72.88 Å²	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	87.94 m³·mol^-1	Chemaxon
Polarizability	33.11 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0006-1093000000-862dc160dc8f327d0da9
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-056r-0495500000-f7ac02c54627a27faafa
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-001i-0397000000-0e08dc88a42e413750ce
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-001i-0029000000-1366c290ed86c001f05b
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03dr-0069000000-a523751ea781088af897
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0009000000-f29d9954b2b055b62079
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-01qi-0039000000-9cb66ef0790c686ea2b2
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0089000000-c501b014ce11307842e1
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0092000000-3f2bc2af8897693f406a
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0290000000-97cd08c23e39dd2412ec
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0690000000-c683e1591a42526bd85d
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0009000000-c8783567d83c0158dc21
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-01qi-0049000000-0c3e1fd26ebdc13a760e
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0079000000-84eeb4205e8a902133ec
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0192000000-3bebeb08e817739aa5f7
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0290000000-40a5de8dd981d46dbe88
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0690000000-827770181ddec7977048
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03dr-0079000000-b9937740f37fc8a939a6
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-001i-0009000000-06b6d10cecb7c9cab240
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-001i-0129000000-61453c8af95773ec6b29
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-03dr-0296000000-de128c8d0e1eade700b6
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0gx1-1292000000-2d8ff05ee839372800db
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-001i-1290000000-f3446636040c80d0f8a3
LC-MS/MS Spectrum - LC-ESI-IT , positive	LC-MS/MS	splash10-000i-0090000000-6fc954ec7c93eaabef55
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001j-0198000000-0bfdea918825b34619d5
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0090000000-5cee2f47095630088ff6
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-01p9-0095000000-c780444ec059d2f2f98e
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-01p9-0095000000-1dc83645e6c6c47ab02f
MS/MS Spectrum - , positive	LC-MS/MS	splash10-014i-0920000000-9769fb468772887a192f
MS/MS Spectrum - , positive	LC-MS/MS	splash10-001i-0397000000-0e08dc88a42e413750ce
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01q9-0009000000-b28b0367b639d90f2e46
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-0019000000-d8b38b79d7d90e22e552
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03di-0009000000-f9addf874edce9f12ce9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00lr-0093000000-4410956982caf1a2cfa9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01p9-0097000000-98e0b1e3c008da6a1619
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00l6-0091000000-af3592ce698870200234
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	188.802573	predicted	DarkChem Lite v0.1.0
[M-H]-	189.275373	predicted	DarkChem Lite v0.1.0
[M-H]-	189.319373	predicted	DarkChem Lite v0.1.0
[M-H]-	172.28362	predicted	DeepCCS 1.0 (2019)
[M+H]+	189.742473	predicted	DarkChem Lite v0.1.0
[M+H]+	190.089073	predicted	DarkChem Lite v0.1.0
[M+H]+	190.213373	predicted	DarkChem Lite v0.1.0
[M+H]+	174.64162	predicted	DeepCCS 1.0 (2019)
[M+Na]+	189.453073	predicted	DarkChem Lite v0.1.0
[M+Na]+	189.831673	predicted	DarkChem Lite v0.1.0
[M+Na]+	189.289373	predicted	DarkChem Lite v0.1.0
[M+Na]+	180.91954	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. DNA topoisomerase 4 subunit A

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92. [Article]

Details2. DNA gyrase subunit A

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]

Details3. DNA topoisomerase 2-alpha

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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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. [Article]
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. [Article]

Details4. Potassium voltage-gated channel subfamily H member 2

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

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. [Article]

Details5. DNA gyrase subunit A

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

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. [Article]

Details6. DNA topoisomerase 4 subunit A

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

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. [Article]

Details7. DNA topoisomerase 4 subunit B

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

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. [Article]

Details8. DNA gyrase subunit A

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

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. [Article]

Details9. Multidrug resistance protein MdtK

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

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. [Article]

Details10. Gyrase A

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

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. [Article]

Details11. DNA gyrase subunit A

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

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. [Article]

Enzymes

Details1. Cytochrome P450 1A2

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

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. [Article]
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. [Article]
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. [Article]
Flockhart Table of Drug Interactions [Link]
Drug Interactions & Labeling - FDA [Link]

Details2. Cytochrome P450 3A4

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

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. [Article]
Flockhart Table of Drug Interactions [Link]
Drug Interactions & Labeling - FDA [Link]
FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]

Details3. Cytochrome P450 3A5

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

Flockhart Table of Drug Interactions [Link]
Drug Interactions & Labeling - FDA [Link]

Details4. Cytochrome P450 3A7

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

Flockhart Table of Drug Interactions [Link]
Drug Interactions & Labeling - FDA [Link]

Carriers

Details1. Serum albumin

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

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. [Article]

Transporters

Details1. P-glycoprotein 1

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

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. [Article]
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. [Article]

Details2. Multidrug and toxin extrusion protein 1

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

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. [Article]
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. [Article]

Details3. Multidrug and toxin extrusion protein 2

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

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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Ciprofloxacin

Identification

Structure for Ciprofloxacin (DB00537)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

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Enzymes

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Carriers

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Transporters

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