Ciprofloxacin hydrochloride

Highest phase reached

Approved

www.ebi.ac.uk

Drug type

Small molecule

www.ebi.ac.uk

First approval year

1987

www.ebi.ac.uk

First approval year: 1987
www.ebi.ac.uk

Listing at source: Listed

Highest phase reached: Approved
www.ebi.ac.uk

Drug type: Small molecule
www.ebi.ac.uk

Drug name: Ciprofloxacin hydrochloride
www.ebi.ac.uk

Molecular weight: 367.81
www.ebi.ac.uk

Structure (SMILES): Cl.O=C(O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O
www.ebi.ac.uk

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

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.

CAS registry numbers

93107-08-5

ChEMBL ID: CHEMBL1202
www.ebi.ac.uk

InChIKey: DIOIOSKKIYDRIQ-UHFFFAOYSA-N
www.ebi.ac.uk

FDA ingredient codes (UNII)

0MP32MFP6C

62999
44350862
46856324
171114757

81981
235851

Applicant: BAYER HLTHCARE
Approval date: 22 Oct 1987
Application number: NDA019537

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

Drug name stem: -oxacin

Administration routes

Oral
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

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

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

Warning
Black Box Warning
Effect
cardiotoxicity
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
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
clinicaltrials.gov

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

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

Recorded assays: 745
Active assays: 32

Confirmatory
Other

Anti-Bacterial Agents
id.nlm.nih.gov
Topoisomerase II Inhibitors
id.nlm.nih.gov
Cytochrome P-450 CYP1A2 Inhibitors
id.nlm.nih.gov

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

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
Otitis externa
Pyelonephritis
Urinary tract infection

In development for (1)

Rectal cancer Phase 2

Ciprofloxacin hydrochloride

Development status

Names and chemistry

Brand names (20)

Other names (37)

Identifiers

PubChem compound IDs (4)

RxNorm IDs (RxCUI) (2)

Regulatory information

United States

Other regulatory facts

Pharmacology

Drug classification

Administration routes

Mechanisms of action (4)

Open Targets mechanisms (2)

Investigated indications (6)

Open Targets indications (12)

Warnings (3)

Open Targets warnings (3)

Reported adverse events (19)

Trial references

Dosing

Conditions of use

Chemical properties

Evidence counts

Active assay types (2)

Pharmacologic actions

Biological measurements

Observed measurements

Solubility

Measurement types

Oral bioavailability

Measurement types

Related records

Trials (242)

Approved for (4)

In development for (1)

Other linked conditions (1)