CIPROFLOXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H18FN3O3
Molecular Weight	331.3415
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CN(C2CC2)C3=C(C=C(F)C(=C3)N4CCNCC4)C1=O

InChI

InChIKey=MYSWGUAQZAJSOK-UHFFFAOYSA-N

InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)

HIDE SMILES / InChI

Molecular Formula	C17H18FN3O3
Molecular Weight	331.3415
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021744s016lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.drugs.com/ciprofloxacin.html | https://clinicaltrials.gov/ct2/show/NCT02598362 | https://www.ncbi.nlm.nih.gov/pubmed/25951434

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 Target	Pharmacology	Condition	Potency
DNA topoisomerase 4 subunit B 7 Target ID: CHEMBL3329081 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26119992	Inhibitor 8504
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25951434	Inhibitor 8504		150.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 207 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021744s016lbl.pdf	Curative	Approved 8583	CIPRO Approved Use Ciprofloxacin Tablets, USP are indicated for the treatment of infections caused by susceptible strains of the designated microorganisms in the conditions and patient populations listed below. Please see DOSAGE AND ADMINISTRATION for specific recommendations. Adult Patients Urinary Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Serratia marcescens, Proteus mirabilis, Providencia rettgeri, Morganella morganii, Citrobacter diversus, Citrobacter freundii, Pseudomonas aeruginosa, methicillin-susceptible Staphylococcus epidermidis, Staphylococcus saprophyticus, or Enterococcus faecalis. Acute Uncomplicated Cystitis in females caused by Escherichia coli or Staphylococcus saprophyticus. Chronic Bacterial Prostatitis caused by Escherichia coli or Proteus mirabilis. Lower Respiratory Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Pseudomonas aeruginosa, Haemophilus influenzae, Haemophilus parainfluenzae, or penicillin-susceptible Streptococcus pneumoniae. Also, Moraxella catarrhalis for the treatment of acute exacerbations of chronic bronchitis. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the treatment of presumed or confirmed pneumonia secondary to Streptococcus pneumoniae. Acute Sinusitis caused by Haemophilus influenzae, penicillin-susceptible Streptococcus pneumoniae, or Moraxella catarrhalis. Skin and Skin Structure Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Proteus vulgaris, Providencia stuartii, Morganella morganii, Citrobacter freundii, Pseudomonas aeruginosa, methicillin susceptible Staphylococcus aureus, methicillin susceptible Staphylococcus epidermidis, or Streptococcus pyogenes. Bone and Joint Infections caused by Enterobacter cloacae, Serratia marcescens, or Pseudomonas aeruginosa. Complicated Intra-Abdominal Infections (used in combination with metronidazole) caused by Escherichia coli, Pseudomonas aeruginosa, Proteus mirabilis, Klebsiella pneumoniae, or Bacteroides fragilis. Infectious Diarrhea caused by Escherichia coli (enterotoxigenic strains), Campylobacter jejuni, Shigella boydii † , Shigella dysenteriae, Shigella flexneri or Shigella sonnei † when antibacterial therapy is indicated. Typhoid Fever (Enteric Fever) caused by Salmonella typhi. NOTE: The efficacy of ciprofloxacin in the eradication of the chronic typhoid carrier state has not been demonstrated. Uncomplicated cervical and urethral gonorrhea due to Neisseria gonorrhoeae. Pediatric patients (1 to 17 years of age)Complicated Urinary Tract Infections and Pyelonephritis due to Escherichia coli. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the pediatric population due to an increased incidence of adverse events compared to controls, including events related to joints and/or surrounding tissues. (See WARNINGS, PRECAUTIONS, Pediatric Use , ADVERSE REACTIONS and CLINICAL STUDIES .) Ciprofloxacin, like other fluoroquinolones, is associated with arthropathy and histopathological changes in weight-bearing joints of juvenile animals. (See ANIMAL PHARMACOLOGY .) Adult and Pediatric PatientsInhalational anthrax (post-exposure): To reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. Ciprofloxacin serum concentrations achieved in humans served as a surrogate endpoint reasonably likely to predict clinical benefit and provided the initial basis for approval of this indication.5 Supportive clinical information for ciprofloxacin for anthrax post-exposure prophylaxis was obtained during the anthrax bioterror attacks of October 2001. (See also, INHALATIONAL ANTHRAX – ADDITIONAL INFORMATION ). †Although treatment of infections due to this organism in this organ system demonstrated a clinically significant outcome, efficacy was studied in fewer than 10 patients. If anaerobic organisms are suspected of contributing to the infection, appropriate therapy should be administered. Appropriate culture and susceptibility tests should be performed before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to ciprofloxacin. Therapy with Ciprofloxacin Tablets may be initiated before results of these tests are known; once results become available appropriate therapy should be continued. As with other drugs, some strains of Pseudomonas aeruginosa may develop resistance fairly rapidly during treatment with ciprofloxacin. Culture and susceptibility testing performed periodically during therapy will provide information not only on the therapeutic effect of the antimicrobial agent but also on the possible emergence of bacterial resistance. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Ciprofloxacin Tablets and other antibacterial drugs, Ciprofloxacin Tablets should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date 1990
Infectious diarrhea 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s085,020780s042lbl.pdf	Curative	Approved 8583	CIPRO Approved Use Ciprofloxacin Tablets, USP are indicated for the treatment of infections caused by susceptible strains of the designated microorganisms in the conditions and patient populations listed below. Please see DOSAGE AND ADMINISTRATION for specific recommendations. Adult Patients Urinary Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Serratia marcescens, Proteus mirabilis, Providencia rettgeri, Morganella morganii, Citrobacter diversus, Citrobacter freundii, Pseudomonas aeruginosa, methicillin-susceptible Staphylococcus epidermidis, Staphylococcus saprophyticus, or Enterococcus faecalis. Acute Uncomplicated Cystitis in females caused by Escherichia coli or Staphylococcus saprophyticus. Chronic Bacterial Prostatitis caused by Escherichia coli or Proteus mirabilis. Lower Respiratory Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Pseudomonas aeruginosa, Haemophilus influenzae, Haemophilus parainfluenzae, or penicillin-susceptible Streptococcus pneumoniae. Also, Moraxella catarrhalis for the treatment of acute exacerbations of chronic bronchitis. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the treatment of presumed or confirmed pneumonia secondary to Streptococcus pneumoniae. Acute Sinusitis caused by Haemophilus influenzae, penicillin-susceptible Streptococcus pneumoniae, or Moraxella catarrhalis. Skin and Skin Structure Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Proteus vulgaris, Providencia stuartii, Morganella morganii, Citrobacter freundii, Pseudomonas aeruginosa, methicillin susceptible Staphylococcus aureus, methicillin susceptible Staphylococcus epidermidis, or Streptococcus pyogenes. Bone and Joint Infections caused by Enterobacter cloacae, Serratia marcescens, or Pseudomonas aeruginosa. Complicated Intra-Abdominal Infections (used in combination with metronidazole) caused by Escherichia coli, Pseudomonas aeruginosa, Proteus mirabilis, Klebsiella pneumoniae, or Bacteroides fragilis. Infectious Diarrhea caused by Escherichia coli (enterotoxigenic strains), Campylobacter jejuni, Shigella boydii † , Shigella dysenteriae, Shigella flexneri or Shigella sonnei † when antibacterial therapy is indicated. Typhoid Fever (Enteric Fever) caused by Salmonella typhi. NOTE: The efficacy of ciprofloxacin in the eradication of the chronic typhoid carrier state has not been demonstrated. Uncomplicated cervical and urethral gonorrhea due to Neisseria gonorrhoeae. Pediatric patients (1 to 17 years of age)Complicated Urinary Tract Infections and Pyelonephritis due to Escherichia coli. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the pediatric population due to an increased incidence of adverse events compared to controls, including events related to joints and/or surrounding tissues. (See WARNINGS, PRECAUTIONS, Pediatric Use , ADVERSE REACTIONS and CLINICAL STUDIES .) Ciprofloxacin, like other fluoroquinolones, is associated with arthropathy and histopathological changes in weight-bearing joints of juvenile animals. (See ANIMAL PHARMACOLOGY .) Adult and Pediatric PatientsInhalational anthrax (post-exposure): To reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. Ciprofloxacin serum concentrations achieved in humans served as a surrogate endpoint reasonably likely to predict clinical benefit and provided the initial basis for approval of this indication.5 Supportive clinical information for ciprofloxacin for anthrax post-exposure prophylaxis was obtained during the anthrax bioterror attacks of October 2001. (See also, INHALATIONAL ANTHRAX – ADDITIONAL INFORMATION ). †Although treatment of infections due to this organism in this organ system demonstrated a clinically significant outcome, efficacy was studied in fewer than 10 patients. If anaerobic organisms are suspected of contributing to the infection, appropriate therapy should be administered. Appropriate culture and susceptibility tests should be performed before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to ciprofloxacin. Therapy with Ciprofloxacin Tablets may be initiated before results of these tests are known; once results become available appropriate therapy should be continued. As with other drugs, some strains of Pseudomonas aeruginosa may develop resistance fairly rapidly during treatment with ciprofloxacin. Culture and susceptibility testing performed periodically during therapy will provide information not only on the therapeutic effect of the antimicrobial agent but also on the possible emergence of bacterial resistance. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Ciprofloxacin Tablets and other antibacterial drugs, Ciprofloxacin Tablets should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date 1990
Lower respiratory tract infections 52 Sources: https://www.drugs.com/pro/cipro-iv.html	Curative	Approved 8583	CIPRO Approved Use Ciprofloxacin Tablets, USP are indicated for the treatment of infections caused by susceptible strains of the designated microorganisms in the conditions and patient populations listed below. Please see DOSAGE AND ADMINISTRATION for specific recommendations. Adult Patients Urinary Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Serratia marcescens, Proteus mirabilis, Providencia rettgeri, Morganella morganii, Citrobacter diversus, Citrobacter freundii, Pseudomonas aeruginosa, methicillin-susceptible Staphylococcus epidermidis, Staphylococcus saprophyticus, or Enterococcus faecalis. Acute Uncomplicated Cystitis in females caused by Escherichia coli or Staphylococcus saprophyticus. Chronic Bacterial Prostatitis caused by Escherichia coli or Proteus mirabilis. Lower Respiratory Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Pseudomonas aeruginosa, Haemophilus influenzae, Haemophilus parainfluenzae, or penicillin-susceptible Streptococcus pneumoniae. Also, Moraxella catarrhalis for the treatment of acute exacerbations of chronic bronchitis. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the treatment of presumed or confirmed pneumonia secondary to Streptococcus pneumoniae. Acute Sinusitis caused by Haemophilus influenzae, penicillin-susceptible Streptococcus pneumoniae, or Moraxella catarrhalis. Skin and Skin Structure Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Proteus vulgaris, Providencia stuartii, Morganella morganii, Citrobacter freundii, Pseudomonas aeruginosa, methicillin susceptible Staphylococcus aureus, methicillin susceptible Staphylococcus epidermidis, or Streptococcus pyogenes. Bone and Joint Infections caused by Enterobacter cloacae, Serratia marcescens, or Pseudomonas aeruginosa. Complicated Intra-Abdominal Infections (used in combination with metronidazole) caused by Escherichia coli, Pseudomonas aeruginosa, Proteus mirabilis, Klebsiella pneumoniae, or Bacteroides fragilis. Infectious Diarrhea caused by Escherichia coli (enterotoxigenic strains), Campylobacter jejuni, Shigella boydii † , Shigella dysenteriae, Shigella flexneri or Shigella sonnei † when antibacterial therapy is indicated. Typhoid Fever (Enteric Fever) caused by Salmonella typhi. NOTE: The efficacy of ciprofloxacin in the eradication of the chronic typhoid carrier state has not been demonstrated. Uncomplicated cervical and urethral gonorrhea due to Neisseria gonorrhoeae. Pediatric patients (1 to 17 years of age)Complicated Urinary Tract Infections and Pyelonephritis due to Escherichia coli. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the pediatric population due to an increased incidence of adverse events compared to controls, including events related to joints and/or surrounding tissues. (See WARNINGS, PRECAUTIONS, Pediatric Use , ADVERSE REACTIONS and CLINICAL STUDIES .) Ciprofloxacin, like other fluoroquinolones, is associated with arthropathy and histopathological changes in weight-bearing joints of juvenile animals. (See ANIMAL PHARMACOLOGY .) Adult and Pediatric PatientsInhalational anthrax (post-exposure): To reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. Ciprofloxacin serum concentrations achieved in humans served as a surrogate endpoint reasonably likely to predict clinical benefit and provided the initial basis for approval of this indication.5 Supportive clinical information for ciprofloxacin for anthrax post-exposure prophylaxis was obtained during the anthrax bioterror attacks of October 2001. (See also, INHALATIONAL ANTHRAX – ADDITIONAL INFORMATION ). †Although treatment of infections due to this organism in this organ system demonstrated a clinically significant outcome, efficacy was studied in fewer than 10 patients. If anaerobic organisms are suspected of contributing to the infection, appropriate therapy should be administered. Appropriate culture and susceptibility tests should be performed before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to ciprofloxacin. Therapy with Ciprofloxacin Tablets may be initiated before results of these tests are known; once results become available appropriate therapy should be continued. As with other drugs, some strains of Pseudomonas aeruginosa may develop resistance fairly rapidly during treatment with ciprofloxacin. Culture and susceptibility testing performed periodically during therapy will provide information not only on the therapeutic effect of the antimicrobial agent but also on the possible emergence of bacterial resistance. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Ciprofloxacin Tablets and other antibacterial drugs, Ciprofloxacin Tablets should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date 1990

C_max

Value	Dose	Analyte	Population
2.97 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.56 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	400 mg 2 times / day steady-state, intravenous dose: 400 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
3.59 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	750 mg 2 times / day steady-state, oral dose: 750 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.07 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	400 mg 3 times / day steady-state, intravenous dose: 400 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
1.2 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.4 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.3 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
5.4 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
13.7 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
12.7 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	400 mg 2 times / day steady-state, intravenous dose: 400 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
31.6 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	750 mg 2 times / day steady-state, oral dose: 750 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
32.9 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	400 mg 3 times / day steady-state, intravenous dose: 400 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.8 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
11.6 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
20.2 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
30.8 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
30% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
15 mg/kg 2 times / day steady, oral Recommended Dose: 15 mg/kg, 2 times / day Route: oral Route: steady Dose: 15 mg/kg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	unhealthy, 1 - 17 years Health Status: unhealthy Age Group: 1 - 17 years Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	Disc. AE: Reaction gastrointestinal... Other AEs: Musculoskeletal disorder NOS... AEs leading to discontinuation/dose reduction: Reaction gastrointestinal (3%) Other AEs: Musculoskeletal disorder NOS (9.3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf
7.5 g single, oral Overdose Dose: 7.5 g Route: oral Route: single Dose: 7.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/9531191/	unhealthy, 15 years Health Status: unhealthy Age Group: 15 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9531191/	Disc. AE: Renal tubular necrosis acute... AEs leading to discontinuation/dose reduction: Renal tubular necrosis acute (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/9531191/
12 g single, oral Overdose Dose: 12 g Route: oral Route: single Dose: 12 g Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	healthy, 16 years Health Status: healthy Age Group: 16 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	Disc. AE: Pain epigastric... AEs leading to discontinuation/dose reduction: Pain epigastric (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/
20 mg/kg single, oral Recommended Dose: 20 mg/kg Route: oral Route: single Dose: 20 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/16182896/	unhealthy, 2-15 years Health Status: unhealthy Age Group: 2-15 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16182896/	Other AEs: Vomited... Other AEs: Vomited (58%) Sources: https://pubmed.ncbi.nlm.nih.gov/16182896/
28 g single, oral Overdose Dose: 28 g Route: oral Route: single Dose: 28 g Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	healthy, 29 years Health Status: healthy Age Group: 29 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	Disc. AE: Acute renal failure... AEs leading to discontinuation/dose reduction: Acute renal failure (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/
750 mg 2 times / day steady, oral Highest studied dose Dose: 750 mg, 2 times / day Route: oral Route: steady Dose: 750 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17660035/	unhealthy, > 70 years Health Status: unhealthy Age Group: > 70 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17660035/	Disc. AE: Acute renal failure... AEs leading to discontinuation/dose reduction: Acute renal failure (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17660035/
3 g single, oral Overdose Dose: 3 g Route: oral Route: single Dose: 3 g Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	Disc. AE: Nausea and vomiting... AEs leading to discontinuation/dose reduction: Nausea and vomiting (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/
228 mg 2 times / day steady, intravenous Recommended Dose: 228 mg, 2 times / day Route: intravenous Route: steady Dose: 228 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/	unhealthy, mean 50 years Health Status: unhealthy Age Group: mean 50 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/	Other AEs: Infusion site reactions, Gastrointestinal disorder (NOS)... Other AEs: Infusion site reactions (4.4%) Gastrointestinal disorder (NOS) (3%) Central nervous system disorder NOS (1.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/
10 mg/kg 2 times / day steady, intravenous Recommended Dose: 10 mg/kg, 2 times / day Route: intravenous Route: steady Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15523125/	unhealthy, preterm neonates Health Status: unhealthy Age Group: preterm neonates Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/15523125/	Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/15523125/
500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/	unhealthy, ≥18 years Health Status: unhealthy Age Group: ≥18 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/	Disc. AE: Myalgia... AEs leading to discontinuation/dose reduction: Myalgia (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/
500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/	unhealthy, ≥18 years Health Status: unhealthy Age Group: ≥18 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/	Disc. AE: Exanthema... AEs leading to discontinuation/dose reduction: Exanthema (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/
500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	Other AEs: Acute kidney injury, Clostridium difficile infection... Other AEs: Acute kidney injury (serious, 8 patients) Clostridium difficile infection (serious, 1 patient) Chest pain (serious, 1 patient) Dysuria (serious, 1 patient) Epistaxis (serious, 1 patient) GI bleed (serious, 1 patient) Hematuria (serious, 1 patient) Hyperkalemia (serious, 1 patient) Hypertension malignant (serious, 1 patient) Myocardial infarction (serious, 1 patient) Nausea (serious, 1 patient) Nephrolithiasis (serious, 1 patient) Neutropenia (serious, 1 patient) Pain (serious, 1 patient) Nephrostomy complication (serious, 1 patient) Radial nerve palsy (serious, 1 patient) Sepsis (serious, 2 patients) Small bowel obstruction (serious, 1 patient) Thrombocytopenia (serious, 1 patient) Urinary incontinence (serious, 1 patient) Urinary retention (serious, 3 patients) Vomiting (serious, 2 patients) Venous thromboembolism (serious, 5 patients) Wound complication (serious, 3 patients) Constipation (below serious, 12 patients) Headache (below serious, 7 patients) Hypomagnesemia (below serious, 8 patients) Insomnia (below serious, 8 patients) Osteopenia (below serious, 19 patients) Proteinuria (below serious, 12 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
500 mg 2 times / day steady, oral Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00609973	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00609973	Other AEs: Diarrhea, Abdominal pain... Other AEs: Diarrhea (below serious, 2 patients) Abdominal pain (below serious, 2 patients) Headache (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00609973
500 mg 2 times / day steady, oral Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT02068846	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT02068846	Other AEs: Rash... Other AEs: Rash (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT02068846

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2E1 1060 CYP4A1 8 CYP2B6 926 CYP2C8 1057 OAT1 725 OAT3 747 OATP1B1 1079 OATP1B3 961 BSEP 550 MRP2 499 MRP3 246 MRP4 290 CYP2A6 879 CYP2C19 2057 ALDH1 41 P-gp 1741	P-gp 2052 BCRP 697 OAT1 395

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
ALDH1 41	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	inconclusive [Activation 10 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMOCJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://gut.bmj.com/content/44/3/347.short, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no [IC50 >10 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	no
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/	no
CYP4A1 25	inhibitor 4027 Sources: https://gut.bmj.com/content/44/3/347.short	no
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18381565/	no
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	no
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	no
P-gp 1932	inhibitor 4027 Sources: https://pubs.acs.org/doi/10.1021/tx010125x, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	yes [Activation 12.5893 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15058617/, https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=085721331, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	yes [Activation 15.84893 uM]	yes (co-administration study) Comment: Coadministration of Ciprofloxacin increased average Clozapine (CYP1A2 substrate) concentration by approximately 30% and Theophylline blood concentration and average half-life by about 20 to 30%.. Sources: https://pubmed.ncbi.nlm.nih.gov/15058617/, https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=085721331, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15058617/, https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=085721331, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMOCJ9fQ%3D%3D	yes [IC50 >10 uM]
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18381565/	yes

Drug as victim

Target	Modality	Activity
P-gp 2052	substrate 4014 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1038/sj.bjp.0704560	no
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18200507/	yes
OAT1 395	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20190787/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjQxMzQ3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/17303420/, http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=21690, https://pubmed.ncbi.nlm.nih.gov/21443219/, https://www.sciencedirect.com/science/article/pii/S0960894X05004038, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMOCJ9fQ%3D%3D

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:100241	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:100241
ChemicalBook	CB22670034	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB22670034
ChemicalBook	CB52630301	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB52630301
eMolecules	485830	https://www.emolecules.com/cgi-bin/more?vid=485830
MolPort	MolPort-000-724-354	https://www.molport.com/shop/molecule-link/MolPort-000-724-354
MolPort	MolPort-000-819-654	https://www.molport.com/shop/molecule-link/MolPort-000-819-654
Selleck Chemicals	ciprofloxacin-cipro	http://www.selleckchem.com/products/ciprofloxacin-cipro.html
ZINC	ZINC000000020220	http://zinc15.docking.org/substances/ZINC000000020220

PubMed

Title	Date	PubMed
Mixed pharmacokinetic population study and diffusion model to describe ciprofloxacin lung concentrations.	2001-05	11173053
What have we learned from pharmacokinetic and pharmacodynamic theories?	2001-03-15	11249828
Successful treatment of an infant with Chromobacterium violaceum sepsis.	2001-03-15	11247733
Treatment failure with the use of ciprofloxacin for gonorrhea correlates with the prevalence of fluoroquinolone-resistant Neisseria gonorrhoeae strains in Bangladesh.	2001-03-15	11247712
In vitro susceptibilities to topical antibiotics of bacteria isolated from the surface of clinically symptomatic eyes.	2001-03-13	11244359
Ciprofloxacin resistance in gonococci.	2001-03-10	11253997
Transepithelial intestinal excretion of ciprofloxacin in humans.	2001-03-01	11229852
Bacteriologic and clinical efficacy of ofloxacin 0.3% versus ciprofloxacin 0.3% ophthalmic solutions in the treatment of patients with culture-positive bacterial keratitis.	2001-03	11248824
Chryseobacterium (Flavobacterium) meningosepticum outbreak associated with colonization of water taps in a neonatal intensive care unit.	2001-03	11247678
A case of rhinoscleroma treated with ciprofloxacin.	2001-03	11244532
Chryseobacterium in burn wounds.	2001-03	11226658
Multi-drug resistant Pseudomonas aeruginosa outbreak in a burns unit--an infection control study.	2001-03	11226649
The activity of antibiotics against Legionella pneumophila: in vitro and in vivo studies.	2001-03	11222573
Characterization of high-level fluoroquinolone resistance in Escherichia coli O78:K80 isolated from turkeys.	2001-03	11222567
Factors associated with antibiotic resistance in coliform organisms from community urinary tract infection in Wales.	2001-03	11222563
Antimicrobial activity of fluoroquinolone photodegradation products determined by parallel-line bioassay and high performance liquid chromatography.	2001-03	11222559
Pediatric travel consultation in an integrated clinic.	2001-02-22	11182602
Radical meatoplasty in the treatment of severe chronic external otitis.	2001-02-15	11174061
In vitro activity of gemifloxacin against Streptococcus pneumoniae isolates in Germany.	2001-02-15	11173811
Association between antibiotic resistance and the expression of Dr adhesin among uropathogenic Escherichia coli.	2001-02-15	11173810
Activity of moxifloxacin and twelve other antimicrobial agents against 216 clinical isolates of Streptococcus pneumoniae.	2001-02-15	11173809
Activity and spectrum of BMS 284756, a new des-F (6) quinolone, tested against strains of ciprofloxacin-resistant Gram-positive cocci.	2001-02	11248528
Effect of pre-stain viability on the acid-fast staining characteristics of Mycobacterium species.	2001-02	11248525
Antimicrobial susceptibilities and plasmid patterns of Neisseria gonorrhoeae in Bénin.	2001-02	11236110
Would you get your Gonorrhoea treated in the north of England?	2001-02	11236101
Neisseria gonorrhoeae resistant to ciprofloxacin: first report in Cuba.	2001-02	11234790
Impact of gemifloxacin on the normal human intestinal microflora.	2001-02	11233800
[Effect of subinhibitory levels of aminoglycosides and fluoroquinolines on hydrophobicity and motility of Serratia marcescens].	2001-02	11233670
Epithelial infectious crystalline keratopathy.	2001-02	11228305
Lack of interaction between levofloxacin and oxycodone: pharmacokinetics and drug disposition.	2001-02	11210403
Treatment of cat-scratch disease.	2001-02	11176245
Nosocomial pneumonia: importance of recognition of aetiological agents to define an appropriate initial empirical therapy.	2001-02	11165120
Activity of gatifloxacin and ciprofloxacin in combination with other antimicrobial agents.	2001-02	11165113
Changes in strategies for optimal antibacterial therapy in cystic fibrosis.	2001-02	11165111
Emergence of high level ciprofloxacin resistant Neisseria gonorrhoeae strain in Buenos Aires, Argentina.	2001-02	11158704
New approach for accurate simulation of human pharmacokinetics in an in vitro pharmacodynamic model: application to ciprofloxacin.	2001-02	11157913
[Acute pyelonephritis. Randomized multicenter double-blind study comparing ciprofloxacin with combined ciprofloxacin and tobramycin].	2001-01-13	11210578
Comparative activities of isepamicin, amikacin, cefepime, and ciprofloxacin alone or in combination with other antibiotics against Stenotrophomonas maltophilia.	2001-01	11245333
Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries.	2001-01	11245326
Two short peptides including segments of subunit A of Escherichia coli DNA gyrase as potential probes to evaluate the antibacterial activity of quinolones.	2001-01	11245203
Comamonas acidovorans keratitis in a hydrogel contact lens wearer.	2001-01	11215608
Microbiological profile of a shipboard environment and the flora on contact lenses of seamen.	2001-01	11215606
Antimicrobial use and susceptibility rates in isolates from intensive care unit and other nosocomial inpatient and outpatient areas.	2001-01	11209842
Determination by fluorimetric titration of the ionization constants of ciprofloxacin in solution and in the presence of liposomes.	2001-01	11202360
Nosocomial pneumonia. Diagnostic and therapeutic considerations.	2001-01	11190353
Insect wing case: unusual foreign body.	2001-01	11188995
Efficacy of ofloxacin and other otic preparations for otitis externa.	2001-01	11176588
Compliance issues related to the selection of antibiotic suspensions for children.	2001-01	11176558
Urethral stricture associated with malacoplakia: a case report and review of the literature.	2001-01	11164174
The role of fluoroquinolones in tuberculosis today.	2001	11217874

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:27:30 GMT 2025` Edited by `admin` on `Mon Mar 31 21:27:30 GMT 2025`
Record UNII	5E8K9I0O4U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CIPROFLOXACIN

Official Name

English

CIPRODEX COMPONENT CIPROFLOXACIN

Preferred Name

English

CIPROFLOXACIN [MART.]

Common Name

English

CIPROFLOXACIN [MI]

Common Name

English

BAY-Q-3939

Code

English

CIPROFLOXACIN [WHO-IP]

Common Name

English

CIPROFLOXACINUM [WHO-IP LATIN]

Common Name

English

CIPROFLOXACIN [USAN]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-

Systematic Name

English

BAY Q 3939

Code

English

CIPROFLOXACIN [JAN]

Common Name

English

ciprofloxacin [INN]

Common Name

English

CIPROFLOXACIN [USP MONOGRAPH]

Common Name

English

CIPROFLOXACIN [USP-RS]

Common Name

English

BAY O 9867 FREE BASE

Code

English

1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINE-CARBOXYLIC ACID

Systematic Name

English

CIPROFLOXACIN [EP MONOGRAPH]

Common Name

English

CIPROFLOXACIN [VANDF]

Common Name

English

BAY-O-9867 FREE BASE

Code

English

ENROFLOXACIN FOR VETERINARY USE IMPURITY B [EP IMPURITY]

Common Name

English

CIPROFLOXACIN [HSDB]

Common Name

English

OTIPRIO

Brand Name

English

NSC-758467

Code

English

BAYQ3939

Code

English

CIPROFLOXACIN [ORANGE BOOK]

Common Name

English

Ciprofloxacin [WHO-DD]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

422314