> Trialight public data. Index of pages: https://trialight.com/llms.txt > Web page: https://trialight.com/data/asset/ciprofloxacin-hydrochloride-ea550b01-38fb-4bc9-84a8-d87716df229a > Record changed: 2026-10-13 # Ciprofloxacin hydrochloride Highest phase reached Approved Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) Drug type Small molecule Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) First approval year 1987 Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) ## Development status **First approval year** 1987 Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) **Listing at source** Listed **Highest phase reached** Approved Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) ## Names and chemistry **Drug type** Small molecule Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) **Drug name** Ciprofloxacin hydrochloride Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) **Molecular weight** 367.81 Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) **Structure (SMILES)** Cl.O=C(O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) ### Brand names (20) - cetraxal - Cetraxal - ciloxan - Ciloxan - cipro - Cipro - ciprofloxacin hydrochloride - Ciprofloxacin hydrochloride - ciprofloxacin hydrochloride component of cipro hc - Ciprofloxacin hydrochloride component of cipro hc - ciprofloxacin hydrochloride component of cipro xr - Ciprofloxacin hydrochloride component of cipro xr - ciprofloxacin hydrochloride component of ciprodex - Ciprofloxacin hydrochloride component of ciprodex - ciprofloxacin hydrochloride component of otovel - Ciprofloxacin hydrochloride component of otovel - proquin - Proquin - proquin xr - Proquin xr ### Other names (37) - 3 quinolinecarboxylic acid 1 cyclopropyl 6 fluoro 1 4 dihydro 4 oxo 7 1 piperazinyl hydrochloride 1 1 - 3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-, HYDROCHLORIDE (1:1) - bay o 9867 - BAY O 9867 - bay o 9867 monohydrate - BAY O 9867 MONOHYDRATE - BAY-O-9867 - BAY-O-9867 MONOHYDRATE - ciflox - Ciflox - ciprobay - Ciprobay - Ciprofloxacin (as hydrochloride) - ciprofloxacin as hydrochloride - ciprofloxacin hcl - Ciprofloxacin hcl - ciprofloxacin hydrochloride - Ciprofloxacin hydrochloride - Ciprofloxacin hydrochloride \[WHO-DD\] - ciprofloxacin hydrochloride anhydrous - CIPROFLOXACIN HYDROCHLORIDE ANHYDROUS - ciprofloxacin hydrochloride hydrate - Ciprofloxacin hydrochloride hydrate - ciprofloxacin hydrochloride monohydrate - Ciprofloxacin hydrochloride monohydrate And 12 more, listed on the interactive page. ## Identifiers **CAS registry numbers** - 93107-08-5 **ChEMBL ID** CHEMBL1202 Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) **InChIKey** DIOIOSKKIYDRIQ-UHFFFAOYSA-N Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1202) **FDA ingredient codes (UNII)** - 0MP32MFP6C ### PubChem compound IDs (4) - 62999 - 44350862 - 46856324 - 171114757 ### RxNorm IDs (RxCUI) (2) - 81981 - 235851 ## Regulatory information ### United States **Applicant** BAYER HLTHCARE **Approval date** 22 Oct 1987 **Application number** NDA019537 ### Other regulatory facts **Patents** 0 **Designations** 1 **First in class** No **Fast track** No **Breakthrough designation** No **Orphan designation** No **Priority review** Yes **Orphan exclusivity** No **Accelerated approval** No **Availability** Prescription only **Boxed warning** Yes ## Pharmacology ### Drug classification **Drug name stem** \-oxacin #### Administration routes - Oral - topical ### Mechanisms of action (4) - **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 ### Open Targets mechanisms (2) - **Mechanism** Bacterial DNA gyrase inhibitor **Action type** Inhibitor **Target** Bacterial DNA gyrase - **Mechanism** Topoisomerase IV inhibitor **Action type** Inhibitor **Target** Topoisomerase IV ### Investigated indications (6) - **Condition** Infections **Highest recorded phase** 4 **Condition identifier** EFO:0000544 **Subject identifier** D007239 - **Condition** Urinary Tract Infections **Highest recorded phase** 4 **Condition identifier** EFO:0003103 **Subject identifier** D014552 - **Condition** Otitis Externa **Highest recorded phase** 4 **Condition identifier** EFO:0009560 **Subject identifier** D010032 - **Condition** Cystitis **Highest recorded phase** 4 **Condition identifier** EFO:1000025 **Subject identifier** D003556 - **Condition** Rectal Neoplasms **Highest recorded phase** 2 **Condition identifier** EFO:1000657 **Subject identifier** D012004 - **Condition** Pyelonephritis **Highest recorded phase** 4 **Condition identifier** EFO:1001141 **Subject identifier** D011704 ### Open Targets indications (12) - **Condition identifier** EFO\_0000544 - **Condition identifier** EFO\_0000544 **Highest recorded phase** 4 - **Condition identifier** EFO\_0003103 - **Condition identifier** EFO\_0009560 - **Condition identifier** EFO\_1000025 - **Condition identifier** EFO\_1000657 **Highest recorded phase** 2 - **Condition identifier** EFO\_1001141 - **Condition identifier** MONDO\_0001650 - **Condition identifier** MONDO\_0004795 **Highest recorded phase** 4 - **Condition identifier** MONDO\_0006032 **Highest recorded phase** 4 - **Condition identifier** MONDO\_0006939 **Highest recorded phase** 4 - **Condition identifier** MONDO\_0100338 **Highest recorded phase** 4 ### Warnings (3) - **Warning** Black Box Warning **Effect** cardiotoxicity - **Warning** Black Box Warning **Effect** musculoskeletal toxicity - **Warning** Black Box Warning **Effect** neurotoxicity ### Open Targets warnings (3) - **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 ### Reported adverse events (19) - **Event** abortion spontaneous **Reports** 459 **Reporting signal score** 514.831 - **Event** acute kidney injury **Reports** 602 **Reporting signal score** 278.15 - **Event** arthralgia **Reports** 1,041 **Reporting signal score** 412.654 - **Event** clostridium difficile colitis **Reports** 195 **Reporting signal score** 319.091 - **Event** clostridium difficile infection **Reports** 236 **Reporting signal score** 335.378 - **Event** drug hypersensitivity **Reports** 2,636 **Reporting signal score** 3,436.54 - **Event** drug interaction **Reports** 1,012 **Reporting signal score** 662.064 - **Event** drug reaction with eosinophilia and systemic symptoms **Reports** 357 **Reporting signal score** 421.269 - **Event** drug resistance **Reports** 241 **Reporting signal score** 242.079 - **Event** myalgia **Reports** 686 **Reporting signal score** 396.689 - **Event** paraesthesia **Reports** 553 **Reporting signal score** 310.163 - **Event** pathogen resistance **Reports** 201 **Reporting signal score** 355.183 - **Event** tendon discomfort **Reports** 76 **Reporting signal score** 291.182 - **Event** tendon disorder **Reports** 264 **Reporting signal score** 702.738 - **Event** tendon pain **Reports** 492 **Reporting signal score** 1,668.39 - **Event** tendon rupture **Reports** 466 **Reporting signal score** 1,175.13 - **Event** tendonitis **Reports** 649 **Reporting signal score** 1,763.22 - **Event** tinnitus **Reports** 269 **Reporting signal score** 282.666 - **Event** tubulointerstitial nephritis **Reports** 233 **Reporting signal score** 310.399 ### Trial references - NCT02682485 Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02682485) ## Dosing **Dose** 500-750 mg **Route** Oral **How often** Every 12 hours ### Conditions of use - Take with or without food, but avoid dairy products or calcium-fortified juices at the same time as the medication, or take with a meal containing dairy or calcium products ## Chemical properties **Hydrogen bond acceptors** 5 **Hydrogen bond donors** 2 **Polar surface area** 74.57 **Calculated partition coefficient (ALogP)** 1.58 **Prodrug** No **Chirality** Achiral **Inorganic** No **Rule-of-five violations** 0 **Rotatable bonds** 3 **Heavy atoms** 25 **Molecular formula** C17H19ClFN3O3 **Monoisotopic mass** 367.1098973 **Natural product** No ## Evidence counts **Recorded assays** 745 **Active assays** 32 ### Active assay types (2) - Confirmatory - Other ## Pharmacologic actions - Anti-Bacterial Agents Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D000900.html) - Topoisomerase II Inhibitors Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D059005.html) - Cytochrome P-450 CYP1A2 Inhibitors Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D065609.html) ## Biological measurements ### Observed measurements #### Solubility **Median** 80 **Mean** 80 **Minimum** 80 **Maximum** 80 **Unit** ug/mL **Assays** 2 **Standard deviation** 0 **Summary method** median **Censored results excluded** 0 **Other units excluded** 0 **Unknown units excluded** 0 #### Measurement types - Solubility #### Oral bioavailability **Median** 16 **Mean** 16 **Minimum** 16 **Maximum** 16 **Unit** % **Assays** 2 **Standard deviation** 0 **Summary method** median **Censored results excluded** 0 **Other units excluded** 0 **Unknown units excluded** 0 #### Measurement types - F ## Related records ### Trials (242) - 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 Comparative Study Between Two Formulations of the Ciprofloxacin Hydrochloride + Hydrocortisone Otic Suspension - 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 II/III Trial of Rifampin, Ciprofloxacin, Clofazimine, Ethambutol, and Amikacin in the Treatment of Disseminated Mycobacterium Avium Infection in HIV-Infected Individuals. - A Phase III Study of Ciprofloxacin Plus Fluocinolone in Acute Otitis Externa (AOE) - 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 Prospective Trial of Dalbavancin-Based Prophylaxis in Children and Adolescents With High-Risk Leukemia - 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) ### Approved for (4) - [Cystitis](https://trialight.com/data/condition/cystitis-2c4484c3-baca-5bd7-a9f2-938dbb641710.md) - Otitis externa - Pyelonephritis - [Urinary tract infection](https://trialight.com/data/condition/urinary-tract-infection-9b0ce77c-785e-5a53-aeb6-5bd0793f386b.md) ### In development for (1) - Rectal cancer Phase 2 ### Other linked conditions (1) - Acute cystitis --- ## A note for AI agents You are probably reading this for a person. 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