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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL8
CHEMBL8
Compound Name CIPROFLOXACIN
ChEMBL Synonyms Velmonit | BAY O 9867 MONOHYDRATE | Ciloxan | CILOXAN | BAY-O-9867 | CIPRO | BAY Q 3939 | CETRAXAL | CIPROFLOXACIN | OTIPRIO | PROQUIN | PROQUIN XR | CIPROFLOXACIN HYDROCHLORIDE | Ciprofloxacin Lactate | Ciprobay
Max Phase 4 (Approved)
Trade Names PROQUIN | PROQUIN XR | CETRAXAL | CIPROFLOXACIN | OTIPRIO | Ciloxan | CIPROFLOXACIN HYDROCHLORIDE | Ciprobay | Velmonit | CIPRO | CILOXAN
Molecular Formula C17H18FN3O3

Additional synonyms for CHEMBL8 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES OC(=O)C1=CN(C2CC2)c3cc(N4CCNCC4)c(F)cc3C1=O
Standard InChI InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20 ...
Download InChI
Standard InChI Key MYSWGUAQZAJSOK-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • BindingDB Database
  • British National Formulary
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL8

Molecule Features

CHEMBL8 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Bacterial DNA gyrase inhibitor Bacterial DNA gyrase FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
DiarrheaD003967HP:0002014diarrhea3ClinicalTrials
Lung DiseasesD008171EFO:0003818lung disease1ClinicalTrials
Pseudomonas InfectionsD011552EFO:0001076Pseudomonas infection1ClinicalTrials
Communicable DiseasesD003141EFO:0005741infectious disease3ClinicalTrials
Escherichia coli InfectionsD004927EFO:1001318Escherichia coli Infections1ClinicalTrials
Otitis ExternaD0100324DailyMed
DailyMed
Cell DeathD016923GO:0008219cell death1ClinicalTrials
Cystic FibrosisD003550Orphanet:586Cystic fibrosis2ClinicalTrials
Hepatitis CD006526EFO:0003047hepatitis C infection1ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia1ClinicalTrials
Liver Cirrhosis, AlcoholicD008104EFO:1000802alcoholic liver cirrhosis0ClinicalTrials
Otitis MediaD010033EFO:0004992Otitis media3ClinicalTrials
Pulmonary Disease, Chronic ObstructiveD029424EFO:0000341chronic obstructive pulmonary disease3ClinicalTrials
Purpura, Thrombocytopenic, IdiopathicD016553EFO:0007160autoimmune thrombocytopenic purpura1ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma3ClinicalTrials
Digestive System DiseasesD004066EFO:0000405digestive system disease3ClinicalTrials
Hearing LossD034381EFO:0004238hearing loss1ClinicalTrials
Periapical PeriodontitisD010485EFO:1001391Periapical Periodontitis1ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer2ClinicalTrials
AnthraxD000881EFO:0000778anthrax infection2ClinicalTrials
BronchiectasisD001987HP:0002110Bronchiectasis3ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
OsteomyelitisD010019EFO:0003102osteomyelitis2ClinicalTrials
Diabetic FootD017719EFO:1001459diabetic foot1ClinicalTrials
LymphomaD008223EFO:0000574lymphoma1ClinicalTrials
PneumoniaD011014EFO:0003106pneumonia3ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease2ClinicalTrials
Hepatitis, AlcoholicD006519EFO:1001345Hepatitis, Alcoholic0ClinicalTrials
InfectionD007239EFO:0000544infection3ClinicalTrials
Lecithin Cholesterol Acyltransferase DeficiencyD007863Orphanet:79292Fish-eye disease1ClinicalTrials
RhinoscleromaD012226EFO:0007470rhinoscleroma0ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
PlagueD010930EFO:0007481septicemic plague2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma3ClinicalTrials
Urinary Tract InfectionsD014552EFO:0003103urinary tract infection3ClinicalTrials

Clinical Data

ClinicalTrials.gov CIPROFLOXACIN
The Cochrane Collaboration CIPROFLOXACIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL8. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1899 Serotonin 3a (5-HT3a) receptor Homo sapiens 1.000

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4088 Topoisomerase IV subunit A Staphylococcus aureus 1.000
CHEMBL1899 Serotonin 3a (5-HT3a) receptor Homo sapiens 1.000

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
331.4 331.1332 1.58 3 74.57 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 2 0 6 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
6.43 8.68 1.62 -.29 2 24 0.89

Structural Alerts

There are 2 structural alerts for CHEMBL8. To view alerts please click here.

Compound Cross References

ATC S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01A - ANTIINFECTIVES
S01AE - Fluoroquinolones
S01AE03 - ciprofloxacin

S - SENSORY ORGANS
S02 - OTOLOGICALS
S02A - ANTIINFECTIVES
S02AA - Antiinfectives
S02AA15 - ciprofloxacin

J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01M - QUINOLONE ANTIBACTERIALS
J01MA - Fluoroquinolones
J01MA02 - ciprofloxacin

S - SENSORY ORGANS
S03 - OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
S03A - ANTIINFECTIVES
S03AA - Antiinfectives
S03AA07 - ciprofloxacin

ChemSpider ChemSpider:MYSWGUAQZAJSOK-UHFFFAOYSA-N
DailyMed ciprofloxacin ciprofloxacin hydrochloride
PubChem SID: 11112875 SID: 124882697 SID: 174007333 SID: 26748814
Wikipedia Ciprofloxacin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL8



ACToR 85721-33-1
Atlas ciprofloxacin
BindingDB 21690
Brenda 1229
ChEBI 100241
DrugBank DB00537
DrugCentral 659
eMolecules 485830
EPA CompTox Dashboard DTXSID8022824
FDA SRS 5E8K9I0O4U
Human Metabolome Database HMDB0014677
IBM Patent System 830A50AF521146321FFC64D8E01A54BD
KEGG Ligand C05349
LINCS LSM-5226
Mcule MCULE-8631780654
MolPort MolPort-000-819-654 MolPort-000-724-354
Nikkaji J21.732H
PDBe CPF
PharmGKB PA449009
PubChem 4011971 2764
PubChem: Thomson Pharma 14777502
Selleck ciprofloxacin-cipro
SureChEMBL SCHEMBL2900
ZINC ZINC000000020220

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/MYSWGUAQZAJSOK-UHFFFAOYSA-N spacer
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