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Details

Stereochemistry ACHIRAL
Molecular Formula 2C17H18FN3O3.2ClH.3H2O
Molecular Weight 789.651
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIPROFLOXACIN HYDROCHLORIDE SESQUIHYDRATE

SMILES

O.O.O.Cl.Cl.OC(=O)C1=CN(C2CC2)C3=CC(N4CCNCC4)=C(F)C=C3C1=O.OC(=O)C5=CN(C6CC6)C7=CC(N8CCNCC8)=C(F)C=C7C5=O

InChI

InChIKey=SMFVXHJJUFAKBS-UHFFFAOYSA-N
InChI=1S/2C17H18FN3O3.2ClH.3H2O/c2*18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24;;;;;/h2*7-10,19H,1-6H2,(H,23,24);2*1H;3*1H2

HIDE SMILES / InChI

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
150.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CIPRO
Curative
CIPRO
Curative
CIPRO

Cmax

ValueDoseCo-administeredAnalytePopulation
4.56 μg/mL
400 mg 2 times / day steady-state, intravenous
CIPROFLOXACIN serum
Homo sapiens
2.97 μg/mL
500 mg 2 times / day steady-state, oral
CIPROFLOXACIN serum
Homo sapiens
2.4 μg/mL
500 mg single, oral
CIPROFLOXACIN serum
Homo sapiens
4.3 μg/mL
750 mg single, oral
CIPROFLOXACIN serum
Homo sapiens
5.4 μg/mL
1000 mg single, oral
CIPROFLOXACIN serum
Homo sapiens
3.59 μg/mL
750 mg 2 times / day steady-state, oral
CIPROFLOXACIN serum
Homo sapiens
4.07 μg/mL
400 mg 3 times / day steady-state, intravenous
CIPROFLOXACIN serum
Homo sapiens
1.2 μg/mL
250 mg single, oral
CIPROFLOXACIN serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
12.7 μg × h/mL
400 mg 2 times / day steady-state, intravenous
CIPROFLOXACIN serum
Homo sapiens
13.7 μg × h/mL
500 mg 2 times / day steady-state, oral
CIPROFLOXACIN serum
Homo sapiens
11.6 μg × h/mL
500 mg single, oral
CIPROFLOXACIN serum
Homo sapiens
20.2 μg × h/mL
750 mg single, oral
CIPROFLOXACIN serum
Homo sapiens
30.8 μg × h/mL
1000 mg single, oral
CIPROFLOXACIN serum
Homo sapiens
31.6 μg × h/mL
750 mg 2 times / day steady-state, oral
CIPROFLOXACIN serum
Homo sapiens
32.9 μg × h/mL
400 mg 3 times / day steady-state, intravenous
CIPROFLOXACIN serum
Homo sapiens
4.8 μg × h/mL
250 mg single, oral
CIPROFLOXACIN serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
500 mg 2 times / day steady-state, oral
CIPROFLOXACIN serum
Homo sapiens
4 h
500 mg single, oral
CIPROFLOXACIN serum
Homo sapiens
4 h
750 mg single, oral
CIPROFLOXACIN serum
Homo sapiens
4 h
1000 mg single, oral
CIPROFLOXACIN serum
Homo sapiens
4 h
250 mg single, oral
CIPROFLOXACIN serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
30%
500 mg 2 times / day steady-state, oral
CIPROFLOXACIN serum
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Skin and Skin Structure 500 -750 mg every 12 hours 7 to 14 days Bone and Joint 500-750 mg every 12 hours 4 to 8 weeks Complicated Intra-Abdominal 500 mg every 12 hours 7 to 14 days Infectious Diarrhea 500 mg every 12 hours 5 to 7 days Typhoid Fever 500 mg every 12 hours 10 days Uncomplicated Gonorrhea 250 mg single dose single dose Inhalational anthrax (pos-exposure) 500 mg every 12 hours 60 days Plague 500–750 mg every 12 hours 14 days Chronic Bacterial Prostatitis 500 mg every 12 hours 28 days Lower Respiratory Tract 500 -750 mg every 12 hours 7 to 14 days Urinary Tract 250-500 mg every 12 hours 7 to 14 days Acute Uncomplicated Cystitis 250 mg every 12 hours 3 days Acute Sinusitis 500 mg every 12 hours 10 days
Route of Administration: Oral
In Vitro Use Guide
Eight hospital isolates of methicillin-resistant and two standard strains of S. epidermidis (ATCC 12228, ATCC 35984) were cultured overnight in Tryptone Soy Broth supplemented with 0.5% glucose. The solution of tested compounds in TSB-glucose medium were mixed (1:1) with the bacterial inoculums (10^7 CFU/mL) in sterile 96-well polystyrene microtiter plates (Karell - Medlab, Italy) and incubated at 37 C for 24 h. Ciprofloxacin was used as the reference antimicrobial compound; its final concentration ranged from 0.125 to 8 mkg/ml.