Ciprofloxacin

Summary

Ciprofloxacin (CHEMBL8) is an approved small-molecule antiinfective agent (ATC J01MA02); indicated across 61 conditions including urinary tract infection and cystitis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J01MA02 (+3 more)
• Indications: 61 conditions
• Clinical trials: 182
• Chemistry: 331.34 Da · C17H18FN3O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL8
Name	Ciprofloxacin
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	2764
ChEBI	CHEBI:100241
ATC	J01MA02, S03AA07, S01AE03, S02AA15
Molecular formula	C17H18FN3O3
Molecular weight	331.34
InChIKey	MYSWGUAQZAJSOK-UHFFFAOYSA-N

SMILES: C1CC1N2C=C(C(=O)C3=CC(=C(C=C32)N4CCNCC4)F)C(=O)O

IUPAC name: 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid

ChEBI definition: A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.

Pharmacological roles (ChEBI): antiinfective agent, topoisomerase IV inhibitor, antibacterial drug, EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, DNA synthesis inhibitor, antimicrobial agent.

Other ChEBI roles (chemical / environmental): environmental contaminant, xenobiotic.

Also known as: BAY O 9867 FREE BASE, BAY Q 3939, BAY-O-9867 FREE BASE, BAY-Q-3939, BAYQ3939, Cetraxal, Cipro, Ciprofloxacin, Ciprofloxacin component of ciprodex, Ciprofloxacine, Ciprofloxacino, Ciprofloxacinum

Parent form; salt/anhydrous children: CHEMBL1202, CHEMBL1077975, CHEMBL3764828, CHEMBL4303345

Patent coverage: 30,246 distinct patent families (97,708 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 21 (assay-derived). Sample: Lysine-specific demethylase 4E, Prelamin-A/C, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Multidrug resistance protein MdtK, DNA gyrase subunit A, DNA topoisomerase 4 subunit A, GABA-A receptor; anion channel, DNA gyrase subunit B, DNA gyrase, DNA topoisomerase II.

Bioactivity

ChEMBL activities: 47 potent at pChembl ≥ 5 of 74 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
Q9QYN8	9.18	Ki	0.65	nM	CHEMBL_ACT_12183328
TOP2A	7.52	EC50	30	nM	CHEMBL_ACT_369758
P0AES4	7.35	IC50	45	nM	CHEMBL_ACT_24843785
P0AES4	6.91	IC50	122	nM	CHEMBL_ACT_19238232
P0AES4	6.82	IC50	150	nM	CHEMBL_ACT_15230379
P0AES4	6.77	IC50	170	nM	CHEMBL_ACT_18740492
P0AES4	6.75	IC50	180	nM	CHEMBL_ACT_29208442
P0AES4	6.7	IC50	200	nM	CHEMBL_ACT_15081648
P0AES4	6.7	IC50	200	nM	CHEMBL_ACT_1775037
P0AES4	6.7	IC50	200	nM	CHEMBL_ACT_22430183
P0AES4	6.64	IC50	230	nM	CHEMBL_ACT_24794678
P0AES4	6.57	IC50	270	nM	CHEMBL_ACT_15073370
P0AES4	6.55	IC50	280	nM	CHEMBL_ACT_19239704
P0AES4	6.52	IC50	300	nM	CHEMBL_ACT_1667304
P0AES4	6.52	IC50	300	nM	CHEMBL_ACT_1695469
P0AES4	6.52	IC50	300	nM	CHEMBL_ACT_3495060
P0AES4	6.51	IC50	310	nM	CHEMBL_ACT_18473352
O09028	6.39	IC50	410	nM	CHEMBL_ACT_604322
P0AES4	6.36	IC50	440	nM	CHEMBL_ACT_22476946
P0AES4	6.31	IC50	490	nM	CHEMBL_ACT_20666584
P0AES4	6.3	IC50	500	nM	CHEMBL_ACT_19440474
P0AES4	6.3	IC50	500	nM	CHEMBL_ACT_591630
P0C1S7	6.26	IC50	550	nM	CHEMBL_ACT_24390247
P0AES4	6.22	IC50	600	nM	CHEMBL_ACT_24692546
P0AES4	6.18	IC50	661	nM	CHEMBL_ACT_24964489
P0AES4	6.08	IC50	830	nM	CHEMBL_ACT_24390267
P0C1U9	6	IC50	1000	nM	CHEMBL_ACT_1689579
P0C1U9	6	IC50	1000	nM	CHEMBL_ACT_1695450
P0AES4	6	IC50	1000	nM	CHEMBL_ACT_19131628
P0AES4	6	IC50	1000	nM	CHEMBL_ACT_3543338

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

61 indications (12 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
urinary tract infection	4	MONDO:0100338	EFO:0003103
cystitis	4	MONDO:0006032	EFO:1000025
bacterial infectious disease	4	MONDO:0005113	EFO:0000771
otitis externa	4	MONDO:0004795	EFO:0009560
pyelonephritis	4	MONDO:0006939	EFO:1001141
eye infectious disorder	4	MONDO:0043885	EFO:1001888
prostatitis	4	MONDO:0005280	EFO:0003830
gonorrhea	4	MONDO:0004277	DOID:7551
chronic bronchitis	4	MONDO:0005607	EFO:0006505
typhoid fever	4	MONDO:0005619	EFO:0006789
sinusitis	4	MONDO:0005961	EFO:0007486
chronic obstructive pulmonary disease	3	MONDO:0005002	EFO:0000341
diarrheal disease	3	MONDO:0001673	HP:0002014
bronchiectasis	3	MONDO:0004822	HP:0002110
infectious disease	3	MONDO:0005550	EFO:0005741
otitis media	3	MONDO:0005441	EFO:0004992
pneumonia	3	MONDO:0005249	EFO:0003106
infectious peritonitis	3	MONDO:0004522	EFO:0008588
neutropenia	3	MONDO:0001475	MONDO:0001475
breast neoplasm	3	MONDO:0021100	MONDO:0007254
urolithiasis	3	MONDO:0024647	MONDO:0024647
plague	3	MONDO:0019095	EFO:0009425
hypertriglyceridemia	3	MONDO:0005347	EFO:0004211
nephrolithiasis	3	MONDO:0008171	EFO:0004253
anthrax infection	2	MONDO:0005119	EFO:0000778
Crohn disease	2	MONDO:0005011	EFO:0000384
B-cell chronic lymphocytic leukemia	2	MONDO:0004948	EFO:0000095
exocrine pancreatic carcinoma	2	MONDO:0005192	EFO:0002618
amyotrophic lateral sclerosis	2	MONDO:0004976	MONDO:0004976
cataract	2	MONDO:0005129	MONDO:0005129
cystic fibrosis	2	MONDO:0009061	MONDO:0009061
endophthalmitis	2	MONDO:0016047	MONDO:0016047
corneal ulcer	2	MONDO:0004577	MONDO:0004577
autoimmune thrombocytopenic purpura	1	MONDO:0008558	EFO:0007160
hepatitis C virus infection	1	MONDO:0005231	EFO:0003047
acute myeloid leukemia	1	MONDO:0018874	EFO:0000222
lymphoma	1	MONDO:0005062	EFO:0000574
neoplasm	1	MONDO:0005070	EFO:0000616
Pseudomonas infection	1	MONDO:0005141	EFO:0001076
lung disorder	1	MONDO:0005275	EFO:0003818
hearing loss disorder	1	MONDO:0005365	EFO:0004238
rhinoscleroma	1	MONDO:0005945	EFO:0007470
periapical periodontitis	1	MONDO:0004508	EFO:1001391
gastroenteritis	1	MONDO:0002269	EFO:1001463
rheumatoid arthritis	1	MONDO:0008383	EFO:0000685
shigellosis	1	MONDO:0019345	EFO:0005585
pancreatic ductal adenocarcinoma	1	MONDO:0005184	MONDO:0005184
osteomyelitis	0	MONDO:0005246	EFO:0003102
alcoholic liver cirrhosis	0	MONDO:0006644	EFO:1000802
alcoholic hepatitis	0	MONDO:0001505	EFO:1001345
erectile dysfunction	0	MONDO:0005362	EFO:0004234

10 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 182.

Phase distribution

Phase	Trials
PHASE4	43
PHASE3	37
Not specified	37
PHASE2	30
PHASE1	27
EARLY_PHASE1	4
PHASE1/PHASE2	3
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT04444440	PHASE4	RECRUITING	Antibiotic Prophylaxis for Bladder Botox
NCT05398679	PHASE4	RECRUITING	Oral Antimicrobial Treatment vs. Outpatient Parenteral for Infective Endocarditis
NCT05846399	PHASE4	RECRUITING	CAT BITE Antibiotic Prophylaxis for the Hand/Forearm (CATBITE)
NCT06709196	PHASE4	RECRUITING	Clinical Trial Testing Whether Targeted Antibiotic Prophylaxis Can Reduce Infections After Cystectomy Compared to Empiric Prophylaxis
NCT07016165	PHASE4	RECRUITING	Ciprofloxacin vs Ceftazidime for Empirical Treatment of High-Risk Neutropenic Fever in Children With Hematologic Malignancies
NCT00126698	PHASE4	COMPLETED	Prophylactic Antibiotics on Urethral Catheter Withdrawal
NCT00392275	PHASE4	COMPLETED	Penetrance of Third Generation Fluoroquinolones in Eyes With Functioning Filtering Blebs
NCT00669994	PHASE4	COMPLETED	Trial to Evaluate the Efficacy and Safety of Cipro® XR in Treating Female Patients With Lower Urinary Tract Infections
NCT00760032	PHASE4	WITHDRAWN	Lipopolysaccharide Binding Protein and Development of Infectious Events in Cirrhotic Patients
NCT01265173	PHASE4	COMPLETED	Comparison of Efficacy of Cefotaxime, Ceftriaxone, and Ciprofloxacin for the Treatment of SBP in Patients With LC
NCT01542801	PHASE4	COMPLETED	Norfloxacin Versus Ciprofloxacin for Spontaneous Bacterial Peritonitis (SBP) Prevention
NCT01649635	PHASE4	COMPLETED	Study of Cabazitaxel Combined With Prednisone and Prophylaxis of Neutropenia Complications in the Treatment of Patients With Metastatic Castration-resistant Prostate Cancer
NCT01659866	PHASE4	COMPLETED	Antibiotic Prophylaxis for Transrectal Prostate Biopsy
NCT01723150	PHASE4	COMPLETED	Antibiotics for Klebsiella Liver Abscess Study
NCT01772615	PHASE4	COMPLETED	Treatment of Ulcerative Colitis With Ciprofloxacin and E. Coli Nissle
NCT01789203	PHASE4	COMPLETED	Ciprofloxacin for Prevention of BK Infection
NCT01803191	PHASE4	COMPLETED	Efficacy Study of Prophylaxis With Fosfomycin Versus Ciprofloxacin Prior Prostate Biopsy
NCT01888822	PHASE4	TERMINATED	Antibiotic Prophylaxis in Laparoscopic Cholecystectomy
NCT02173262	PHASE4	COMPLETED	REaCT Integrated Consent Model to Compare Two Standard of Care Regimens
NCT02261896	PHASE4	COMPLETED	Antibiotic Prophylaxis for Endoscopic Ultrasound Guided Fine Needle Aspiration of Pancreatic Cystic Lesions
NCT02375295	PHASE4	UNKNOWN	Struvite Stones Antibiotic Study
NCT02423759	PHASE4	COMPLETED	A Trial Assessing Peri-procedure Chemoprophylaxis During Transrectal Prostate Needle Biopsy
NCT02458781	PHASE4	UNKNOWN	Antibiotic Treatment Trial for Small Intestinal Bacterial Overgrowth
NCT02598362	PHASE4	COMPLETED	Pharmacokinetics of Ciprofloxacin in Pediatric Patients
NCT02724046	PHASE4	COMPLETED	Ciprofloxacin for the Prevention of Meningococcal Meningitis
NCT02790138	PHASE4	COMPLETED	A Study to Evaluate the Efficacy and Safety of Vedolizumab in the Treatment of Chronic Pouchitis
NCT02816112	PHASE4	COMPLETED	Granulocyte-colony Stimulating Factors or Antibiotics for Primary Prophylaxis for Febrile Neutropenia
NCT02967341	PHASE4	UNKNOWN	Blood Draw Validation for Ciprofloxacin Pharmacokinetic Research in Pediatric Cancer Patients
NCT03012360	PHASE4	TERMINATED	Antimicrobial Treatment in Patients With Ventilator-associated Tracheobronchitis
NCT03228108	PHASE4	COMPLETED	Culture-guided Antimicrobial Prophylaxis in Men Undergoing Prostate Biopsy.
NCT03262142	PHASE4	TERMINATED	Targeted AntiBiotics for Chronic Pulmonary Diseases
NCT03347461	PHASE4	WITHDRAWN	Otiprio Versus Ciprodex Tympanostomy Tube Outcomes
NCT03366207	PHASE4	COMPLETED	Efficacy of Ciprofloxacin for the Treatment of Uncomplicated Urinary Tract Infection (uUTI)
NCT03431675	PHASE4	WITHDRAWN	Ciprofloxacin for the Prevention of Meningococcal Meningitis 2018
NCT03533231	PHASE4	COMPLETED	Efficiency of Triple Antibiotic Paste, Ciprofloxacin/Propolis, Ciprofloxacin/Metronidazole, Propolis/Metronidazole Combinations on Revascularization Process of Immature Necrotic Maxillary Incisors of Patients 8-18 Years Old.
NCT03692715	PHASE4	COMPLETED	Antibiotic Prophylaxis Before Shock Wave Lithotripsy
NCT03854929	PHASE4	COMPLETED	Ciprofloxacin Versus Azithromycin for Children Hospitalised With Dysentery
NCT04456712	PHASE4	COMPLETED	Effect of Ciprofloxacin Versus Levofloxacin on QTc-interval and Dysglycemia
NCT04948463	PHASE4	COMPLETED	Early Versus Late Stopping of Antibiotics in Children With Cancer and High-risk Febrile Neutropenia
NCT05274672	PHASE4	WITHDRAWN	Role of Prophylactic Postoperative Antibiotics in HoLEP

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of CPIC Guideline for aminosalicylic acid, chloramphenicol,	CPIC	G6PD

PharmGKB also curates 1 clinical and 7 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).