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ciprofloxacin

Trade name: cipro

Small moleculeapproved

Approved

Oct 22, 1987

Ciprofloxacin (1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid) is the synthetic antimicrobial agent for oral or intravenous administration. Ciprofloxacin is a member of the fluoroquinolone class of antibacterial agents. The bactericidal action of ciprofloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV (both Type II topoisomerases), which are required for bacterial DNA replication, transcription, repair, and recombination. Ciprofloxacin is used to treat a wide variety of infections, including infections of bones and joints, endocarditis, gastroenteritis, malignant otitis externa, respiratory tract infections, cellulitis, urinary tract infections, prostatitis, anthrax, and chancroid. In the United States, ciprofloxacin is pregnancy category C. This category includes drugs for which no adequate and well-controlled studies in human pregnancy exist, and for which animal studies have suggested the potential for harm to the fetus, but potential benefits may warrant use of the drug in pregnant women despite potential risks. Fluoroquinolones have been reported as present in a mother's milk and thus passed on to the nursing child. Oral and intravenous ciprofloxacin is approved by the FDA for use in children for only two indications due to the risk of permanent injury to the musculoskeletal system: Inhalational anthrax (postexposure) and Complicated urinary tract infections and pyelonephritis due to Escherichia coli. — NCATS

Clinical trial activity

283 trials · 307 clinical orgs · 52 marketing orgs

Phase 1
59
Phase 2
119
Phase 3
67
Phase 4
57

Earliest trial started Mar 1, 1995 (NCT00367913)

Timeline

1980s

  1. Oct 22, 1987

    Bayer — Earliest FDA Approval

  2. Oct 22, 1987

    Bayer — NDA Organization

1990s

  1. Dec 31, 1990

    Novartis — NDA Secondary Org

  2. Dec 31, 1990

    Sandoz — NDA Secondary Org

  3. Jan 1, 1996

    Earliest Phase 3 Sponsor(trial)

  4. Jan 1, 1997

    Earliest Phase 2 Sponsor(trial)

  5. Jan 1, 1999

    Earliest Phase 1 Sponsor(trial)

2000s

  1. Mar 16, 2004

    AiPing Pharm Inc — Marketing Organization

  2. Mar 16, 2004

    Fosun — Marketing Organization

  3. Jun 9, 2004

    Amneal Pharmaceuticals — Marketing Organization

  4. Jun 9, 2004

    Pharmaceutical Associates — Marketing Organization

  5. Jun 9, 2004

    Barr Laboratories — Marketing Organization

  6. Jun 9, 2004

    Ani Pharmaceuticals — Marketing Organization

  7. Jun 9, 2004

    Teligent Pharmaceuticals — Marketing Organization

  8. Jun 9, 2004

    Watson Pharmaceuticals — Marketing Organization

  9. Jun 9, 2004

    Ionis Pharmaceuticals, Inc. — Marketing Organization

  10. Jun 9, 2004

    Rubicon Research — Marketing Organization

  11. Jun 9, 2004

    Hikma — Marketing Organization

  12. Jun 9, 2004

    Nostrum Laboratories — Marketing Organization

  13. Jun 9, 2004

    Sun Pharmaceuticals — Marketing Organization

  14. Jun 9, 2004

    Natco Pharma — Marketing Organization

  15. Jun 9, 2004

    THE J MOLNER — Marketing Organization

  16. Sep 10, 2004

    Unique Pharmaceuticals Ltd, India — Marketing Organization

  17. Oct 6, 2004

    Taro Pharmaceuticals — Marketing Organization

  18. Nov 4, 2004

    Chartwell Pharmaceuticals — Marketing Organization

  19. Nov 4, 2004

    Apotex — Marketing Organization

  20. May 19, 2005

    Assertio — NDA Secondary Org

  21. Jun 15, 2005

    Pliva — Marketing Organization

  22. Sep 21, 2005

    Teva — Marketing Organization

  23. Aug 28, 2006

    Fresenius — Marketing Organization

  24. Aug 28, 2006

    Dr. Reddy's Laboratories — Marketing Organization

  25. Aug 28, 2006

    Hospira — Marketing Organization

  26. Dec 13, 2006

    Rising Pharmaceuticals — Marketing Organization

  27. Mar 22, 2007

    Mylan — Marketing Organization

  28. Apr 26, 2007

    Aurobindo Pharma — Marketing Organization

  29. Nov 27, 2007

    Anchen Pharmaceuticals, Inc — Marketing Organization

  30. Nov 27, 2007

    Endo Pharmaceuticals — Marketing Organization

  31. Jan 16, 2008

    Amring Pharmaceticals — Marketing Organization

  32. Mar 18, 2008

    Bedford Pharmaceuticals — Marketing Organization

  33. Mar 18, 2008

    Inforlife — Marketing Organization

  34. Mar 18, 2008

    Baxalta — Marketing Organization

  35. Mar 18, 2008

    Baxter — Marketing Organization

  36. Jun 30, 2008

    FDC — Marketing Organization

  37. Dec 11, 2008

    Akorn, Inc. — Marketing Organization

  38. Dec 11, 2008

    Sciegen Pharmaceticals — Marketing Organization

  39. May 1, 2009

    Wraser Pharmaceuticals — NDA Secondary Org

  40. May 1, 2009

    KEY THERAP — Marketing Organization

2010s

  1. Nov 30, 2010

    Actavis — Marketing Organization

  2. Mar 5, 2014

    Lupin — Marketing Organization

  3. Dec 10, 2015

    Otonomy, Inc. — NDA Secondary Org

  4. Dec 10, 2015

    ALK-Abello, S.A. — Marketing Organization

  5. Dec 10, 2015

    ALK-Abello, S.A. — NDA Secondary Org

  6. Apr 29, 2016

    Salvat — Marketing Organization

  7. Apr 29, 2016

    Salvat — NDA Secondary Org

  8. May 3, 2018

    Altair Therapeutics — Marketing Organization

  9. Jun 22, 2018

    Yiling Pharmaceutical Inc. — Marketing Organization

2020s

  1. Jun 9, 2023

    SENTISS — Marketing Organization

  2. Nov 5, 2024

    Identirx — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

Approval history

  • approvedPriority reviewOct 22, 1987

Chemistry & pharmacology

Loading structure…

SMILES

O=C(O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O
Mol. weight
331.35 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral, Parenteral, Topical
Availability
Prescription Only

Oral

Yes

Parenteral

Yes

Topical

Yes

Black box warning

Sources

Also known as

  • 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
  • 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-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-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-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-(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
  • 1-cyclopropyl-6-fluoro-7-hexahydro-1-pyrazinyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
  • bay-o-9867
  • bay-o-9867
  • bay-o-9867 monohydrate
  • bay-o-9867 monohydrate
  • bay-q-3939
  • bay-q-3939
  • cetraxal
  • cetraxal
  • ciloxan
  • ciloxan
  • cipro
  • cipro
  • cipro
  • cipro
  • ciprobay
  • ciprobay
  • ciprodex
  • ciprodex
  • ciprofloxacillin
  • ciprofloxacin
  • ciprofloxacin
  • ciprofloxacin
  • ciprofloxacin
  • ciprofloxacin
  • ciprofloxacin
  • ciprofloxacin
  • ciprofloxacin
  • ciprofloxacin
  • ciprofloxacin
  • ciprofloxacin
  • ciprofloxacine
  • ciprofloxacine
  • ciprofloxacine
  • ciprofloxacin hcl
  • ciprofloxacin hcl
  • ciprofloxacin hcl
  • ciprofloxacin hydrochloride
  • ciprofloxacin hydrochloride
  • ciprofloxacin hydrochloride
  • ciprofloxacin hydrochloride
  • ciprofloxacin hydrochloride
  • ciprofloxacin hydrochloride monohydrate
  • ciprofloxacin lactate
  • ciprofloxacino
  • ciprofloxacino
  • ciprofloxacinum
  • ciprofloxacinum
  • cyprofloxacine
  • df289
  • fluoroquinolone
  • fluoroquinolone
  • proquin
  • proquin
  • proquin xr
  • proquin xr
  • velmonit
  • velmonit

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06926322N/AOct 31, 2025Ain Shams University
NCT07028424Phase 2Jul 31, 2025Groupe Cooperateur Multidisciplinaire en Oncologie (GERCOR), Servier
NCT07016165Phase 4Jun 1, 2025Gadjah Mada University
NCT06810583Phase 1May 22, 2025St. Jude Children's Hospital
NCT07150065Phase 2Feb 7, 2025Avicenna Medical Center
NCT06798402Phase 2Feb 7, 2025Al-Mustafa University College, Al-Mustansiriyah University
NCT06716905Phase 1Jan 31, 2025Xiamen Amoytop Biotech Co., Ltd., Xiamen University
NCT06728072Phase 2Dec 15, 2024American Cancer Society, Inc., Virginia Commonwealth University
NCT07188935N/AOct 30, 2024Al-Mustansiriyah University
NCT06342830Phase 2Jun 20, 2024Ain Shams University
NCT05959616Phase 1Mar 1, 2024Johns Hopkins University, PATH, United States Army, United States Navy, University of Oxford, Wellcome Trust
NCT06185543Phase 2Nov 19, 2023NeuroSense Therapeutics Ltd.
NCT06126731Phase 1/Phase 2 (Phase 2)Nov 2, 2023National Health Service, United Kingdom, Prostate Cancer Foundation, University of London
NCT06093191Phase 4Sep 25, 2023Huazhong University of Science and Technology
NCT05846399Phase 4Sep 7, 2023University of Missouri
NCT05977868Phase 4Aug 4, 2023West Virginia University
NCT05750966N/AJul 19, 2023University of Amsterdam, ZonMw: The Netherlands Organisation for Health Research and Development
NCT06234046Phase 3May 28, 2023Ain Shams University
NCT05844735Phase 1May 22, 2023Sanofi
NCT05843708Phase 1Apr 14, 2023Servier
Showing 20 of 283 trials
Page 1 / 15

Organizations

Research & Development (307)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
BayerFor profit211841999
Otonomy, Inc.For profit9932012
National Institute of Allergy and Infectious Diseases (NIAID)Government7631999
NeuroSense Therapeutics Ltd.For profit6622019
NovartisFor profit6032008
University of AmsterdamAcademic/Hospital5312013
University of LondonAcademic/Hospital5432011
University of North Carolina at Chapel HillAcademic/Hospital5332004
Ain Shams UniversityAcademic/Hospital4442015
Iterum TherapeuticsFor profit4422017
National University of SingaporeAcademic/Hospital4342013
Novum Pharmaceutical Research ServicesFor profit4022005
Tel Aviv UniversityAcademic/Hospital4012009
University of CopenhagenAcademic/Hospital4222001
University of PennsylvaniaAcademic/Hospital4321997
University of PoitiersAcademic/Hospital4332006
University of TorontoAcademic/Hospital4222003
University of WashingtonAcademic/Hospital4422004
ZonMw: The Netherlands Organisation for Health Research and DevelopmentAcademic/Hospital4022013
Aradigm CorporationFor profit3322010
307 organizations
Page 1 / 16

Marketing (74)

OrganizationOrg typeRelationshipDate
ALK-Abello, S.A.For profitMKTGDec 10, 2015
ALK-Abello, S.A.For profitNDA2Dec 10, 2015
ActavisFor profitMKTGNov 30, 2010
AiPing Pharm IncFor profitMKTGMar 16, 2004
Akorn, Inc.For profitSYNDec 11, 2008
Akorn, Inc.For profitMKTGDec 11, 2008
Altair TherapeuticsFor profitMKTGMay 3, 2018
Amneal PharmaceuticalsFor profitMKTGJun 9, 2004
Amring PharmaceticalsFor profitMKTGJan 16, 2008
Anchen Pharmaceuticals, IncFor profitMKTGNov 27, 2007
Ani PharmaceuticalsFor profitSYNJun 9, 2004
Ani PharmaceuticalsFor profitMKTGJun 9, 2004
ApotexFor profitMKTGNov 4, 2004
ApotexFor profitSYNJun 9, 2004
AssertioFor profitNDA2May 19, 2005
Aurobindo PharmaFor profitMKTGApr 26, 2007
Barr LaboratoriesFor profitMKTGJun 9, 2004
BaxaltaFor profitSYNMar 18, 2008
BaxaltaFor profitMKTGMar 18, 2008
BaxterFor profitMKTGMar 18, 2008
BayerFor profitSYNDec 26, 1990
BayerFor profitNDAOct 22, 1987
Bedford PharmaceuticalsFor profitMKTGMar 18, 2008
Bedford PharmaceuticalsFor profitSYNSep 23, 2004
Chartwell PharmaceuticalsFor profitMKTGNov 4, 2004
Dr. Reddy's LaboratoriesFor profitMKTGAug 28, 2006
Dr. Reddy's LaboratoriesFor profitSYNJun 9, 2004
Endo PharmaceuticalsFor profitMKTGNov 27, 2007
FDCFor profitMKTGJun 30, 2008
FosunFor profitMKTGMar 16, 2004
FreseniusFor profitMKTGAug 28, 2006
HikmaFor profitMKTGJun 9, 2004
HikmaFor profitSYNApr 21, 2008
HospiraFor profitMKTGAug 28, 2006
IdentirxFor profitMKTGNov 5, 2024
InforlifeFor profitMKTGMar 18, 2008
Ionis Pharmaceuticals, Inc.For profitMKTGJun 9, 2004
KEY THERAPFor profitMKTGMay 1, 2009
LupinFor profitMKTGMar 5, 2014
MylanFor profitSYNJun 9, 2004
MylanFor profitMKTGMar 22, 2007
Natco PharmaFor profitMKTGJun 9, 2004
Nostrum LaboratoriesFor profitMKTGJun 9, 2004
NovartisFor profitSYNDec 31, 1990
NovartisFor profitNDA2Dec 31, 1990
Otonomy, Inc.For profitNDA2Dec 10, 2015
Pharmaceutical AssociatesFor profitMKTGJun 9, 2004
PlivaFor profitMKTGJun 15, 2005
Rising PharmaceuticalsFor profitSYNJun 9, 2004
Rising PharmaceuticalsFor profitMKTGDec 13, 2006
Rising PharmaceuticalsFor profitSYNDec 13, 2006
Rubicon ResearchFor profitMKTGJun 9, 2004
SENTISSFor profitMKTGJun 9, 2023
SalvatFor profitMKTGApr 29, 2016
SalvatFor profitNDA2Apr 29, 2016
SandozFor profitNDA2Dec 31, 1990
Sciegen PharmaceticalsFor profitMKTGDec 11, 2008
Sun PharmaceuticalsFor profitSYNAug 30, 2022
Sun PharmaceuticalsFor profitMKTGJun 9, 2004
THE J MOLNERFor profitMKTGJun 9, 2004
Taro PharmaceuticalsFor profitSYNOct 6, 2004
Taro PharmaceuticalsFor profitMKTGOct 6, 2004
Teligent PharmaceuticalsFor profitMKTGJun 9, 2004
TevaFor profitSYNDec 26, 2001
TevaFor profitMKTGSep 21, 2005
TevaFor profitSYNAug 28, 2006
TevaFor profitSYNJun 9, 2004
Unique Pharmaceuticals Ltd, IndiaFor profitMKTGSep 10, 2004
Unique Pharmaceuticals Ltd, IndiaFor profitSYNSep 10, 2004
Watson PharmaceuticalsFor profitMKTGJun 9, 2004
Watson PharmaceuticalsFor profitSYNJan 21, 2005
Wraser PharmaceuticalsFor profitNDA2May 1, 2009
Yiling Pharmaceutical Inc.For profitSYNJun 22, 2018
Yiling Pharmaceutical Inc.For profitMKTGJun 22, 2018