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Compound Detail

CHEMBL8

CIPROFLOXACIN
💊 Approved Drug
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💊 Approved Drug
O=C(O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL8
Name CIPROFLOXACIN
Phase Approved
Structure Type MOL
InChI Key MYSWGUAQZAJSOK-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

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 +3 more
42
Targets
293
Activities
4
Assay Types
30
PK Parameters
20
Publications
15
Known Names
20
Indications
2
Mechanisms

Molecular Properties

331.4
MW (Da)
1.58
ALogP
5
HBA
2
HBD
74.6
PSA (Ų)
0.89
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1987
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning
USAN Stem -oxacin
USAN Year 1987

Extended Properties

Molecular Formula C17H18FN3O3
MW 331.35
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -0.72

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial DNA gyrase inhibitor INHIBITOR Bacterial DNA gyrase ✓ ✓
Topoisomerase IV inhibitor INHIBITOR Topoisomerase IV ✓ ✓

Indications

Bacterial Infections Bronchitis, Chronic Cystitis Eye Infections Gonorrhea Infections Intraabdominal Infections Otitis Externa Prostatitis Pyelonephritis Sinusitis Typhoid Fever Urinary Tract Infections Breast Neoplasms Bronchiectasis Communicable Diseases Diarrhea Digestive System Diseases Fever Hypertriglyceridemia

ATC Classification

J01MA02
ciprofloxacin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AE03
ciprofloxacin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S02AA15
ciprofloxacin
Level 1: SENSORY ORGANS
Level 2: OTOLOGICALS
S03AA07
ciprofloxacin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS

Drug Warnings

Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
musculoskeletal toxicity
Country: United States

Activity Summary

IC50 282 meas. best 9.52
EC50 8 meas. best 7.66
Kd 2 meas. best 4.04
Ki 1 meas. best 9.18

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Pseudomonas aeruginosa
CHEMBL348
 IC50 9.52 6.6129 0.3 7
Histamine H3 receptor
CHEMBL4124
 Ki 9.18 9.18 0.7 1
Escherichia coli
CHEMBL354
 IC50 8.0 6.7667 10.0 6
Escherichia coli
CHEMBL354
 EC50 7.66 7.66 22.0 1
Unchecked
CHEMBL612545
 IC50 7.52 5.5519 30.0 57
DNA topoisomerase II
CHEMBL2094255
 EC50 7.52 7.52 30.0 1
DNA gyrase
CHEMBL2094139
 IC50 7.35 6.4914 45.0 22
Plasmodium falciparum
CHEMBL364
 IC50 7.3 4.7257 50.0 35
Plasmodium berghei
CHEMBL612653
 IC50 7.22 7.22 60.0 1
Salmonella typhimurium
CHEMBL351
 EC50 7.22 7.02 60.0 2
Staphylococcus aureus
CHEMBL352
 IC50 6.85 6.185 140.0 28
Vibrio cholerae
CHEMBL614402
 IC50 6.7 6.7 200.0 1
Staphylococcus aureus
CHEMBL352
 EC50 6.46 5.6067 350.0 3
GABA-A receptor; anion channel
CHEMBL1907607
 IC50 6.39 5.195 410.0 2
Mycobacterium intracellulare
CHEMBL612640
 IC50 6.38 6.0878 420.0 9
Micrococcus luteus
CHEMBL614421
 IC50 6.3 6.15 500.0 4
Bacillus subtilis
CHEMBL359
 IC50 6.3 6.0217 500.0 6
Topoisomerase IV
CHEMBL3038508
 IC50 6.26 5.2186 550.0 7
Raoultella planticola
CHEMBL613271
 IC50 6.22 6.18 600.0 3
Mycobacterium tuberculosis
CHEMBL360
 IC50 6.22 5.9233 600.0 3
DNA topoisomerase 4 subunit A
CHEMBL4088
 IC50 6.0 5.6325 1000.0 4
DNA gyrase subunit A
CHEMBL1858
 IC50 6.0 5.5325 1000.0 4
Mycolicibacterium smegmatis
CHEMBL613088
 IC50 5.97 5.835 1070.0 2
DNA gyrase
CHEMBL3038482
 IC50 5.94 4.7046 1150.0 13
DNA gyrase subunit B
CHEMBL1921666
 IC50 5.93 5.93 1170.0 1
MCF7
CHEMBL387
 IC50 5.05 4.585 8850.0 2
HBL-100
CHEMBL614811
 IC50 4.99 4.99 10280.0 1
DNA gyrase subunit A/DNA gyrase subunit B
CHEMBL3430898
 IC50 4.97 4.695 10600.0 2
L02
CHEMBL4296457
 IC50 4.91 4.91 12230.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 4.76 4.76 17200.0 1
NCI/ADR-RES
CHEMBL613829
 IC50 4.72 4.72 19120.0 1
DNA topoisomerase 4 subunit B
CHEMBL2150841
 IC50 4.62 4.62 24110.0 1
HepG2
CHEMBL395
 IC50 4.57 4.57 27000.0 1
Streptococcus pneumoniae
CHEMBL347
 IC50 4.55 4.255 28000.0 2
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.45 4.45 35910.0 1
DNA topoisomerase 4 subunit A
CHEMBL1895
 IC50 4.29 4.29 51000.0 1
Trypanosoma brucei gambiense
CHEMBL613768
 IC50 4.28 4.28 52000.0 1
NCI-H460
CHEMBL396
 IC50 4.22 4.22 60000.0 1
THP-1
CHEMBL614245
 IC50 4.22 4.22 60500.0 1
LoVo
CHEMBL614721
 IC50 4.05 4.05 89000.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 4.04 4.04 92050.0 1
Multidrug resistance protein MdtK
CHEMBL1681613
 Kd 4.04 4.04 90900.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.02 4.02 96000.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2300.0 ng.hr.mL-1 -
AUC 20.0 ug ml-1 Canis lupus familiaris
AUC 7.0 - Mus musculus
AUC 20.0 - Canis lupus familiaris
AUC 7000.0 ng.hr.mL-1 Mus musculus
AUC 21000.0 ng.hr.mL-1 Mus musculus
AUC 20000.0 ng.hr.mL-1 Canis lupus familiaris
AUC 2590.0 ng.hr.mL-1 Rattus norvegicus
AUC 4540.0 ng.hr.mL-1 Canis lupus familiaris
AUC 8000.0 ng.hr.mL-1 Mus musculus
AUC 19000.0 ng.hr.mL-1 Mus musculus
AUC 20.0 ug ml-1 Canis lupus familiaris
AUC 12720.0 ng.hr.mL-1 Rattus norvegicus
AUC 2.3 ug ml-1 -
AUC 2300.0 ng.hr.mL-1 Mus musculus
AUC 29000.0 ng.hr.mL-1 Mus musculus
AUC 6600.0 ng.hr.mL-1 Mus musculus
AUC 14100.0 ng.hr.mL-1 Mus musculus
AUC 37700.0 ng.hr.mL-1 Mus musculus
AUC 5950.0 ng.hr.mL-1 Mus musculus
AUC 14430.0 ng.hr.mL-1 Mus musculus
AUC 6200.0 ng.hr.mL-1 Mus musculus
AUC 17835.0 ng.hr.mL-1 Mus musculus
AUC 30000.0 ng.hr.mL-1 Homo sapiens
AUC 17835.0 ng.hr.mL-1 Mus musculus
CL 8.3 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 8.3 mL.min-1.kg-1 Homo sapiens
CL 32.3 L/hr Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Pseudomonas aeruginosa IC50 = 0.3 nM 9.52 Antimicrobial activity against Pseudomonas aeruginosa ATCC 27853 assessed as inh... 31287681
Histamine H3 receptor Ki = 0.654 nM 9.18 Binding affinity to rat cerebral cortex histamine H3 receptor 22483590
Escherichia coli IC50 = 10.0 nM 8.0 Antibacterial activity against Escherichia coli ATCC 35218 by modified CLSI/NCCL... 19879765
Escherichia coli IC50 = 10.0 nM 8.0 Antibacterial activity against Escherichia coli ATCC 35218 after 18 to 24 hrs by... 19344127
Escherichia coli EC50 = 22.0 nM 7.66 Antibacterial activity against Escherichia coli K-12 BW25113 incubated for 18 hr... 31307763
DNA topoisomerase II EC50 = 30.0 nM 7.52 Inhibitory activity against HeLa cell Topoisomerase II -
Unchecked IC50 = 30.0 nM 7.52 Inhibition of Escherichia coli topoisomerase 4 assessed as reduction in decatena... 35231579
Escherichia coli IC50 = 30.0 nM 7.52 Antimicrobial activity against Escherichia coli NCIM 2068 assessed as growth inh... -
Pseudomonas aeruginosa IC50 = 38.0 nM 7.42 Antimicrobial activity against Pseudomonas aeruginosa PAO1 assessed as inhibitio... 22515429
DNA gyrase IC50 = 45.0 nM 7.35 Inhibition of Escherichia coli DNA gyrase supercoiling activity 35231579
Plasmodium falciparum IC50 = 50.0 nM 7.3 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum MRC-2 ... 28237557
Pseudomonas aeruginosa IC50 = 50.0 nM 7.3 Antimicrobial activity against Pseudomonas aeruginosa NCIM 2967 assessed as grow... -
Salmonella typhimurium EC50 = 60.0 nM 7.22 Antibacterial activity against Salmonella typhimurium ATCC14028 infected in mous... 38283231
Plasmodium berghei IC50 = 60.0 nM 7.22 Antimalarial activity against liver stage Plasmodium berghei 37163950
Unchecked IC50 = 100.0 nM 7.0 Inhibition of Escherichia coli DNA gyrase by gel electrophoresis 18519725
DNA gyrase IC50 = 122.0 nM 6.91 Inhibition of Escherichia coli DNA gyrase super-coiling activity using relaxed p... 31279292
Staphylococcus aureus IC50 = 140.0 nM 6.85 Antimicrobial activity against methicillin resistant Staphylococcus aureus ATCC ... 19658408
DNA gyrase IC50 = 150.0 nM 6.82 Inhibition of Escherichia coli DNA gyrase after 1 hr by agarose gel electrophore... 25951434
Salmonella typhimurium EC50 = 150.0 nM 6.82 Antibacterial activity against intracellular multidrug-resistant Salmonella typh... 36439974
DNA gyrase IC50 = 170.0 nM 6.77 Inhibition of Escherichia coli DNA gyrase assessed as inhibition of pUC19 superc... 30034678

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1431
- 10.6019/CHEMBL3885881 Rattus norvegicus 463
20439614 10.1128/aac.00247-10 Bacillus anthracis 221
18824609 10.1128/aac.00222-08 Pseudomonas aeruginosa 182
20937787 10.1128/aac.00672-10 Streptococcus pneumoniae 180
20100879 10.1128/aac.01637-09 Acinetobacter baumannii 135
17261619 10.1128/aac.01278-06 Pseudomonas aeruginosa 91
21173174 10.1128/aac.00927-10 Escherichia coli 85
17893152 10.1128/aac.00830-07 Pseudomonas aeruginosa 77
16980961 10.1038/nchembio820 Staphylococcus aureus 75
19917752 10.1128/aac.00801-09 Salmonella enteritidis 58
17908946 10.1128/aac.00294-07 Salmonella enterica subsp. enterica 55
19307366 10.1128/aac.01531-08 Streptococcus pneumoniae 55
17967915 10.1128/aac.00689-07 Acinetobacter baumannii 52
17967915 10.1128/aac.00689-07 Pseudomonas aeruginosa 51
19635960 10.1128/aac.01664-08 Escherichia coli 51
19029320 10.1128/aac.00132-08 Escherichia coli 50
20498313 10.1128/aac.01670-09 Prescottella equi 50
17950957 10.1016/j.ejmech.2007.08.014 Staphylococcus aureus 48
17043131 10.1128/aac.00600-06 Salmonella typhimurium 44

Data from ChEMBL 36 via Core Engine