Ciprofloxacin
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1987
- First approval year
- 1987
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Ciprofloxacin
- Molecular weight
- 331.35
- Structure (SMILES)
- O=C(O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O
- cetraxal
- Cetraxal
- cipro
- Cipro
- ciprofloxacin
- Ciprofloxacin
- ciprofloxacin component of ciprodex
- Ciprofloxacin component of ciprodex
- otiprio
- Otiprio
- velmonit
- Velmonit
- bay o 9867 free base
- BAY O 9867 FREE BASE
- bay q 3939
- BAY Q 3939
- BAY-O-9867 FREE BASE
- BAY-Q-3939
- bayq3939
- BAYQ3939
- ciprodex component ciprofloxacin
- CIPRODEX COMPONENT CIPROFLOXACIN
- ciprofloxacin
- Ciprofloxacin
- Ciprofloxacin (BAYQ3939) dry powder for inhalation
- CIPROFLOXACIN [EP MONOGRAPH]
- CIPROFLOXACIN [HSDB]
- ciprofloxacin [INN]
- CIPROFLOXACIN [JAN]
- CIPROFLOXACIN [MART.]
- CIPROFLOXACIN [MI]
- CIPROFLOXACIN [ORANGE BOOK]
- CIPROFLOXACIN [USAN]
- CIPROFLOXACIN [USP MONOGRAPH]
- CIPROFLOXACIN [USP-RS]
- CIPROFLOXACIN [VANDF]
- Ciprofloxacin [WHO-DD]
And 32 more, listed on the interactive page.
- CAS registry numbers
- 85721-33-1
- ChEMBL ID
- CHEMBL8
- InChIKey
- MYSWGUAQZAJSOK-UHFFFAOYSA-N
- FDA ingredient codes (UNII)
- 5E8K9I0O4U
- Applicant
- BAYER HLTHCARE
- Approval date
- 22 Oct 1987
- Application number
- NDA019537
- Patents
- 8
- Designations
- 2
- Earliest recorded loss of exclusivity
- 27 Nov 2038
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Boxed warning
- Yes
- United States (FDA)
- Approved
- Pharmacology name
- ciprofloxacin
- Type
- Synthetic organic
- Drug name stem
- -oxacin
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Parenteral
- topical
- Mechanism
- Bacterial DNA gyrase inhibitor
- Action type
- Inhibitor
- Target
- Bacterial DNA gyrase
- Protein identifier
- P0AES4
- Mechanism
- Bacterial DNA gyrase inhibitor
- Action type
- Inhibitor
- Target
- Bacterial DNA gyrase
- Protein identifier
- P0AES6
- Mechanism
- Topoisomerase IV inhibitor
- Action type
- Inhibitor
- Target
- Topoisomerase IV
- Protein identifier
- P0AFI2
- Mechanism
- Topoisomerase IV inhibitor
- Action type
- Inhibitor
- Target
- Topoisomerase IV
- Protein identifier
- P20083
- Mechanism
- Bacterial DNA gyrase inhibitor
- Action type
- Inhibitor
- Target
- Bacterial DNA gyrase
- Mechanism
- Topoisomerase IV inhibitor
- Action type
- Inhibitor
- Target
- Topoisomerase IV
- Action type
- Inhibitor
- Gene symbol
- gyrA
- Protein identifier
- P0AES4
- Organism
- Escherichia coli (strain K12)
- Action type
- Inhibitor
- Gene symbol
- parC
- Protein identifier
- P0C1U9
- Organism
- Staphylococcus aureus
- Condition
- Gonorrhea
- Highest recorded phase
- 4
- Condition identifier
- DOID:7551
- Subject identifier
- D006069
- Condition
- Leukemia, Lymphocytic, Chronic, B-Cell
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000095
- Subject identifier
- D015451
- Condition
- Leukemia, Myeloid, Acute
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000222
- Subject identifier
- D015470
- Condition
- Pulmonary Disease, Chronic Obstructive
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000341
- Subject identifier
- D029424
- Condition
- Crohn Disease
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000384
- Subject identifier
- D003424
- Condition
- Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000544
- Subject identifier
- D007239
- Condition
- Intraabdominal Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000544
- Subject identifier
- D059413
- Condition
- Lymphoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000574
- Subject identifier
- D008223
- Condition
- Neoplasms
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000616
- Subject identifier
- D009369
- Condition
- Arthritis, Rheumatoid
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000685
- Subject identifier
- D001172
- Condition
- Bacterial Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000771
- Subject identifier
- D001424
- Condition
- Anthrax
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000778
- Subject identifier
- D000881
- Condition
- Pseudomonas Infections
- Highest recorded phase
- 1
- Condition identifier
- EFO:0001076
- Subject identifier
- D011552
- Condition
- Pancreatic Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0002618
- Subject identifier
- D010190
- Condition
- Hepatitis C
- Highest recorded phase
- 1
- Condition identifier
- EFO:0003047
- Subject identifier
- D006526
- Condition
- Osteomyelitis
- Highest recorded phase
- 0.5
- Condition identifier
- EFO:0003102
- Subject identifier
- D010019
- Condition
- Urinary Tract Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003103
- Subject identifier
- D014552
- Condition
- Pneumonia
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003106
- Subject identifier
- D011014
- Condition
- Lung Diseases
- Highest recorded phase
- 1
- Condition identifier
- EFO:0003818
- Subject identifier
- D008171
- Condition
- Prostatitis
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003830
- Subject identifier
- D011472
- Condition
- Hypertriglyceridemia
- Highest recorded phase
- 3
- Condition identifier
- EFO:0004211
- Subject identifier
- D015228
- Condition
- Erectile Dysfunction
- Highest recorded phase
- 0.5
- Condition identifier
- EFO:0004234
- Subject identifier
- D007172
- Condition
- Hearing Loss
- Highest recorded phase
- 1
- Condition identifier
- EFO:0004238
- Subject identifier
- D034381
- Condition
- Kidney Calculi
- Highest recorded phase
- 3
- Condition identifier
- EFO:0004253
- Subject identifier
- D007669
- Condition
- Otitis Media
- Highest recorded phase
- 3
- Condition identifier
- EFO:0004992
- Subject identifier
- D010033
And 37 more, listed on the interactive page.
- Condition identifier
- DOID_7551
- Condition identifier
- EFO_0000095
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000341
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000384
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000544
- Condition identifier
- EFO_0000544
- Highest recorded phase
- 4
- Condition identifier
- EFO_0000685
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000771
- Condition identifier
- EFO_0000778
- Highest recorded phase
- 2
- Condition identifier
- EFO_0001076
- Highest recorded phase
- 1
- Condition identifier
- EFO_0003102
- Condition identifier
- EFO_0003103
- Condition identifier
- EFO_0003106
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003818
- Highest recorded phase
- 1
- Condition identifier
- EFO_0003830
- Condition identifier
- EFO_0004211
- Highest recorded phase
- 3
- Condition identifier
- EFO_0004234
- Condition identifier
- EFO_0004238
- Condition identifier
- EFO_0004253
- Condition identifier
- EFO_0004352
- Highest recorded phase
- 3
- Condition identifier
- EFO_0004992
- Highest recorded phase
- 3
- Condition identifier
- EFO_0005585
- Highest recorded phase
- 1
- Condition identifier
- EFO_0005741
- Highest recorded phase
- 3
- Condition identifier
- EFO_0006505
- Condition identifier
- EFO_0006789
And 98 more, listed on the interactive page.
- Warning
- Black Box Warning
- Effect
- musculoskeletal toxicity
- Warning
- Black Box Warning
- Effect
- neurotoxicity
- Warning
- Black Box Warning
- Effect
- cardiotoxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- musculoskeletal toxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- neurotoxicity
- Country
- United States
- Event
- abortion spontaneous
- Reports
- 456
- Reporting signal score
- 528.725
- Event
- acute kidney injury
- Reports
- 589
- Reporting signal score
- 285.431
- Event
- anxiety
- Reports
- 538
- Reporting signal score
- 219.606
- Event
- arthralgia
- Reports
- 997
- Reporting signal score
- 399.584
- Event
- clostridium difficile colitis
- Reports
- 185
- Reporting signal score
- 302.438
- Event
- clostridium difficile infection
- Reports
- 230
- Reporting signal score
- 332.199
- Event
- drug hypersensitivity
- Reports
- 2,663
- Reporting signal score
- 3,625.61
- Event
- drug interaction
- Reports
- 932
- Reporting signal score
- 582.311
- Event
- drug reaction with eosinophilia and systemic symptoms
- Reports
- 311
- Reporting signal score
- 343.284
- Event
- drug resistance
- Reports
- 242
- Reporting signal score
- 253.296
- Event
- myalgia
- Reports
- 675
- Reporting signal score
- 407.286
- Event
- neuropathy peripheral
- Reports
- 416
- Reporting signal score
- 230.173
- Event
- panic attack
- Reports
- 189
- Reporting signal score
- 220.702
- Event
- paraesthesia
- Reports
- 521
- Reporting signal score
- 290.354
- Event
- pathogen resistance
- Reports
- 199
- Reporting signal score
- 359.077
- Event
- tendon discomfort
- Reports
- 75
- Reporting signal score
- 290.071
- Event
- tendon disorder
- Reports
- 255
- Reporting signal score
- 684.792
- Event
- tendon pain
- Reports
- 459
- Reporting signal score
- 1,549.6
- Event
- tendon rupture
- Reports
- 416
- Reporting signal score
- 1,019.73
- Event
- tendonitis
- Reports
- 605
- Reporting signal score
- 1,644.72
- Event
- tinnitus
- Reports
- 265
- Reporting signal score
- 286.38
- Event
- toxic anterior segment syndrome
- Reports
- 88
- Reporting signal score
- 235.534
- Event
- tubulointerstitial nephritis
- Reports
- 220
- Reporting signal score
- 292.113
- NCT00002850
- NCT01659866
- NCT01756924
- NCT01757236
- NCT01789203
- NCT02357407
- NCT02505581
- NCT02734732
- NCT03150082
- NCT03358576
- NCT03840811
- NCT04870138
- NCT05442736
- NCT05863832
- NCT00003824
- NCT00004216
- NCT00107081
- NCT00126698
- NCT00481689
- NCT00598403
- NCT00663806
- NCT00668122
- NCT00669994
- NCT00676533
- NCT00722735
And 88 more, listed on the interactive page.
- Dose
- 500 mg
- Route
- Oral
- How often
- Every 12 hours
- Hydrogen bond acceptors
- 5
- Hydrogen bond donors
- 2
- Polar surface area
- 74.57
- Calculated partition coefficient (ALogP)
- 1.58
- Calculated partition coefficient (XLogP)
- -1.1
- Prodrug
- No
- Chirality
- Achiral
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Molecular formula
- C17H18FN3O3
- Monoisotopic mass
- 331.13321961
- Natural product
- No
- 0409-2300
- 0409-3300
- 25021-114
- 25021-192
- 64950-381
- 84549-300
- Recorded assays
- 22,649
- Active assays
- 1,014
- Confirmatory
- Other
- Summary
- Anti-Bacterial Agents
- Topoisomerase II Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors
These details could not be displayed.
Related records
Trials (240)
- A Bioequivalence Study of Two Ciprofloxacin/Dexamethasone Formulations in Patients With Otitis Externa
- A Clinical Trial to Evaluate the Safety and Efficacy of Ciprofloxacin in the Treatment of Plague in Humans
- A Multicentre, Randomized as a Double Blind Study, Triple Placebo, Comparative of the Efficacy and Safety of an Association Secnidazol-Ciprofloxacin Compared With Amoxicillin-Clavulanic Acid for the Treatment of Uncomplicated Episode of Diverticular Sigmoïditis Among Adults
- A Multiple-Dose PK Study to Evaluate the Comparative Bioavailability of PrimeC Tablets to Ciprofloxacin Tablets Co-administered With Celecoxib Capsules, in Healthy Adult Subject
- A Phase 1 Study to Examine the Drug-Drug Interaction of Ciprofloxacin, Itraconazole, and Rifampin on the Combination of Lumacaftor With Ivacaftor in Healthy Adult Subjects
- A Phase 1, Open-Label Study to Evaluate the Effect of a Low-Fat Meal and Multiple Doses of Ciprofloxacin on the Pharmacokinetics of Vorasidenib in Healthy Subjects
- A Phase Ib Study of Belinostat With RDHAP Chemotherapy (Dexamethasone, Cytarabine, Cisplatinum) in Adults With Relapsed or Refractory Diffuse Large B-cell Lymphoma
- A Phase III Study to Evaluate the Safety, Efficacy and Pharmacokinetics/Pharmacodynamics of BAYQ3939 in Patients With Bacterial Pneumonia
- A Pilot Comparison of Short-course Nitrofurantoin in Females With Uncomplicated Bacterial Cystitis in the Emergency Department
- A Pilot Study of Ciprofloxacin Plus Gemcitabine and Nab-Paclitaxel Chemotherapy in Patients With Metastatic Pancreatic Ductal Adenocarcinoma.
- A Pilot Study on the Use of Prophylactic Antibiotics for EUS-guided Pancreatic Cyst Aspiration
- A Pilot Study to Evaluate the PK Profile of PrimeC-ER Tablets in Healthy Adult Subjects
- A Randomized Placebo- and Active Comparator-controlled Study to Evaluate the Photosafety of SAR441566
- A Study to Evaluate the Efficacy and Safety of Vedolizumab in the Treatment of Chronic Pouchitis
- A Study to Investigate the Phototoxic Potential of Faldaprevir
- A Trial Assessing Peri-procedure Chemoprophylaxis During Transrectal Prostate Needle Biopsy
- A Trial of Fosfomycin vs Ciprofloxacin for Febrile Neutropenia (FOVOCIP)
- Acetic Acid Ear Drops Versus 0.3 % Ciprofloxacin for Chronic Suppurative Otitis Media.
- Adalimumab in Combination With Ciprofloxacin/Placebo Treatment of Perianal Fistulas in Crohn's
- Amoxicillin-clavulanate Alone or in Combination With Ciprofloxacin in Low-Risk Febrile Neutropenic Adult Patients: A Prospective, Double-blind, Randomized, Non-Inferiority Multicenter, Phase III Clinical Trial.
Approved for (12)
- Bacterial infectious disease
- Chronic bronchitis
- Cystitis
- Eye infectious disorder
- Gonorrhea
- Gram-positive bacterial infections
- Otitis externa
- Prostatitis
- Pyelonephritis
- Sinusitis
- Typhoid fever
- Urinary tract infection
In development for (66)
- Acute cystitis Phase 3
- Acute lung injury Phase 2
- Acute myeloid leukemia Phase 1
- Acute otitis externa Phase 3
- Acute pyelonephritis Phase 3
- Alcoholic hepatitis Early phase 1
- Alcoholic liver cirrhosis Early phase 1
- Alzheimer disease Phase 2
- Amyotrophic lateral sclerosis Phase 2
- Anthrax infection Phase 2
- Autoimmune thrombocytopenic purpura Phase 1
- B-cell chronic lymphocytic leukemia Phase 2
- Bacterial pneumonia Phase 3
- Breast cancer Phase 3
- Bronchiectasis Phase 3
- Bubonic plague Phase 3
- Cataract Phase 2
- Chronic obstructive pulmonary disease Phase 3
- Colorectal cancer Phase 2
- Corneal ulcer Phase 2
Other linked conditions (9)
- Acute cholangitis
- Appendicitis
- Cholangitis
- Cirrhosis of liver
- Epilepsy
- Peritonitis
- Skin infection
- Type 2 diabetes mellitus
- Ulcerative colitis