General
Preferred name
CIPROFLOXACIN
Synonyms
Oftacilox ()
Ciprofloxacin hydrochloride hydrate ()
Bay-09867 hydrochloride monohydrate ()
Ceprimax ()
Ciloxan ()
CIPROFLOXACIN HYDROCHLORIDE ()
Ciprofloxacin hydrochloride monohydrate ()
Bay o 9867 ()
Ciproxan ()
Bay-09867 (hydrochloride)Ciprofloxacin HCl ()
Ciprofloxacin XR ()
Ciprofloxacin (hydrochloride monohydrate) ()
Ciprofloxacin (monohydrochloride) ()
Bay-09867 (hydrochloride monohydrate) ()
Bay-09867 ()
Bay-09867 (monohydrochloride) ()
Ciloxan, Ceprimax, Oftacilox,Bay-09867 hydrochloride hydrate ()
CPX, Cetraxal, Ciloxan, Cipro, Bay-09867 hydrochloride ()
Ciprofloxacin (hydrochloride hydrate) ()
NSC-758467 ()
Ciprofloxacin component of ciprodex ()
BAY-Q-3939 ()
Ciprofloxacinum ()
BAY Q 3939 ()
Ciprofloxacino ()
Cetraxal ()
BAYQ3939 ()
Cipro ()
Otiprio ()
Velmonit ()
Ciprofloxacine ()
BAY-O-9867 FREE BASE ()
BAY O 9867 FREE BASE ()
BAY-O-9867 ()
Ciprobay ()
Ciprofloxacini hydrochloridum ()
Ciprofloxacin HCl ()
Ciprofloxacin hydrochloride component of otovel ()
Ciprofloxacin (as hydrochloride) ()
Ciprofloxacin hydrochloride component of ciprodex ()
Ciflox ()
Flociprin ()
Proquin ()
Ciprofloxacin hydrochloride component of cipro hc ()
Ciproxin ()
BAY-O-9867 Monohydrate ()
Ciprofloxacin hydrochloride component of cipro xr ()
BAY O 9867 MONOHYDRATE ()
Cipropol ()
Proquin XR ()
BAY O 9867 ()
Ciprofloxacin-d8 (hydrochloride) ()
Ciprofloxacin monohydrochloride ()
P&D ID
PD000974
CAS
85721-33-1
93107-08-5
86483-48-9
86393-32-0
1216659-54-9
Tags
available
drug
Approved by
FDA
First approval
1987
Drug indication
anthrax infection
Gram-positive bacterial infection
rectum cancer
Cystic fibrosis
Bacterial infection
Biliary cancer
Drug Status
approved
investigational
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS Ciprofloxacin is a second generation fluoroquinolone that is active against many Gram negative and Gram positive bacteria.[A178870,L6469,L6472,L6475,L6478,L6481,L6484,L6487,L6490,L6493] It produces its action through inhibition of bacterial DNA gyrase and topoisomerase IV.[A178885] Ciprofloxacin binds to bacterial DNA gyrase with 100 times the affinity of mammalian DNA gryase.[A178894] There is no cross resistance between fluoroquinolones and other classes of antibiotics, so it may be of clinical value when other antibiotics are no longer effective.[A178894] Ciprofloxain and its derivatives are also being investigated for its action against malaria, cancers, and AIDS.[A178885]
MOA Ciprofloxacin acts on bacterial topoisomerase II (DNA gyrase) and topoisomerase IV.[A178885] Ciprofloxacin's targeting of the alpha subunits of DNA gyrase prevents it from supercoiling the bacterial DNA which prevents DNA replication.[A178876,A178882]
INDICATION Ciprofloxacin is only indicated in infections caused by susceptible bacteria.[L6469,L6472,L6475,L6478,L6481,L6484,L6487,L6490,L6493]; ; Ciprofloxacin immediate release tablets, oral suspensions, and intravenous injections are indicated for the treatment of skin and skin structure infections, bone and joint infections, complicated intra-abdominal infections, nosocomial pneumonia, febrile neutropenia, adults who have inhaled anthrax, plague, chronic bacterial prostatitis, lower respiratory tract infections including acute exacerbations of chronic bronchitis, urinary tract infections, complicated urinary tract infections in pediatrics, complicated pyelonephritis in pediatrics, and acute sinusitis.[L6481,L6478]; ; A ciprofloxacin otic solution and otic suspension with hydrocortisone are indicated for acute otitis externa.[L6469,L6484] Ciprofloxacin suspension with dexamethasone is indicated for acute otitis media in pediatric patients with tympanostomy tubes or acute otitis externa.[L6490] A ciprofloxacin intratympanic injection is indicated for pediatric patients with bilateral otitis media with effusion who are having tympanostomy tubes placed or pediatric patients 6 months or older with acute otitis externa.[L6493]; ; A ciprofloxacin eye drop is indicated for bacterial corneal ulcers and conjunctivitis.[L6472] A ciprofloxacin eye ointment is indicated for bacterial conjunctivitis.[L6475]; ; A ciprofloxacin extended release tablet is indicated for uncomplicated urinary tract infections, complicated urinary tract infections, and acute uncomplicated pyelonephritis.[L6487]
ROE 27% of an oral dose was recovered unmetabolized in urine compared to 46% of an intravenous dose.[A178858] Collection of radiolabelled ciprofloxacin resulted in 45% recovery in urine and 62% recovery in feces.[A178876]
TOXICITY Patients experiencing an overdose may present with nausea, vomiting, abdominal pain, crystalluria, nephrotoxicity, and oliguria.[A178954,A178957,A178960] Ciprofloxacin overdose typically leads to acute renal failure.[A178960] An overdose may progress over the next 6 days with rising serum creatinine and BUN, as well as anuria.[A178957] Patients may require prednisone therapy, urgent hemodialysis, or supportive therapy.[A178954,A178960] Depending on the degree of overdose, patients may recover normal kidney function or progress to chronic kidney failure.[A178960]; ; The oral LD50 in rats is >2000mg/kg.[L6529]; ; Ciprofloxacin for intratympanic injection or otic use has low systemic absorption and so it unlikely to be a risk in pregnancy or lactation.[L6493] There is generally no harm to the fetus in animal studies, however high doses may lead to gastrointestinal disturbances in the mother which may increase the incidence of abortion.[L6490,L6472,L6484,L6475] In human studies there was no increase in fetal malformations above background rates.[L6478,L6481] The risk and benefit of ciprofloxacin should be weighed in pregnancy and breast feeding.[L6490,L6472,L6484,L6478,L6481,L6487,L6475,L6469]; ; 2/8 in vitro tests and 0/3 in vivo tests of mutagenicity of ciprofloxacin have yielded a positive result.[L6493,L6490,L6472,L6484,L6478,L6481,L6487,L6475,L6469]; ; Oral doses of 200 and 300 times the maximum recommended clinical dose in rats and mice have shown no carcinogenicity or tumorigenicity.[L6493,L6472,L6484,L6478,L6481,L6487,L6475,L6469]; ; Oral doses above the maximum recommended clinical dose have shown no effects on fertility in rats.[L6493,L6484,L6478,L6481,L6487,L6475,L6469]
METABOLISM Ciprofloxacin is primarily metabolized by CYP1A2.[L6481] The primary metabolites oxociprofloxacin and sulociprofloxacin make up 3-8% of the total dose each.[L6487] Ciprofloxacin is also converted to the minor metabolites desethylene ciprofloxacin and formylciprofloxacin.[L6487] These 4 metabolites account for 15% of a total oral dose.[L6481]; ; There is a lack of available data on the enzymes and types of reactions involved in forming these metabolites.[A178822,A178819,A178828,A178831]
ABSORPTION A 250mg oral dose of ciprofloxacin reaches an average maximum concentration of 0.94mg/L in 0.81 hours with an average area under the curve of 1.013L/h\*kg.[A178858] The FDA reports an oral bioavailability of 70-80%[Label,A820] while other studies report it to be approximately 60%.[A178858] An early review of ciprofloxacin reported an oral bioavailability of 64-85% but recommends 70% for all practical uses.[A178876]
HALF-LIFE The average half life following a 250mg oral dose was 4.71 hours and 3.65 hours following a 100mg intravenous dose.[A178858] Generally the half life is reported as 4 hours.[Label,A178858]
DESCRIPTION Ciprofloxacin is a synthetic, broad spectrum second generation fluoroquinolone antibacterial. (GtoPdb)
PRICE 29
DESCRIPTION Ciprofloxacin (Bay-09867), a synthetic broad spectrum fluoroquinolone antibiotic, inhibits bacterial DNA gyrase. It is more active against Gram-negative bacteria than Gram-positive bacteria.
PRICE 29
DESCRIPTION Ciprofloxacin monohydrochloride (Bay-09867 hydrochloride) is a broad-spectrum antimicrobial carboxyfluoroquinoline.
DESCRIPTION Ciprofloxacin (Bay-09867) hydrochloride monohydrate is a potent, orally active topoisomerase IV inhibitor. Ciprofloxacin hydrochloride monohydrate induces mitochondrial DNA and nuclear DNA damage and lead to mitochondrial dysfunction, ROS production. Ciprofloxacin hydrochloride monohydrate has anti-proliferative activity and induces apoptosis. Ciprofloxacin hydrochloride monohydrate is a fluoroquinolone antibiotic, exhibiting potent antibacterial activity[1][2][3][4].
DESCRIPTION Ciprofloxacin is a second generation fluoroquinolone that has spawned many derivative antibiotics. It is only indicated in infections caused by susceptible bacteria. (Enamine Bioactive Compounds)
DESCRIPTION Ciprofloxacin hydrochloride monohydrate (Bay-09867 hydrochloride monohydrate) is a fluoroquinolone antibiotic,is an antibiotic used to treat a number of bacterial infections (TargetMol Bioactive Compound Library)
Cell lines
9
Organisms
19
Compound Sets
25
Cayman Chemical Bioactives
14286
25466
ChEMBL Approved Drugs
CHEMBL8
CHEMBL1202
ChEMBL Drugs
CHEMBL8
CHEMBL1202
CZ-OPENSCREEN Bioactive Library
Drug Repurposing Hub
DrugBank
DB00537
DrugBank Approved Drugs
DB00537
DrugCentral
659
DrugCentral Approved Drugs
659
DrugMAP
DM2NLS9
DrugMAP Approved Drugs
DM2NLS9
DrugMatrix
Enamine Bioactive Compounds
EBC-12960
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS102273
Guide to Pharmacology
10902
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL8
MedChem Express Bioactive Compound Library
HY-B0356
HY-B0356A
HY-B0356B
NCATS Inxight Approved Drugs
5E8K9I0O4U
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
ciprofloxacin-hydrochloride
ciprofloxacin-hydrochloride-hydrate
TargetMol Bioactive Compound Library
T8130
The Spectrum Collection
External IDs
107
Properties
(calculated by RDKit )
Molecular Weight
331.13
Hydrogen Bond Acceptors
5
Hydrogen Bond Donors
2
Rotatable Bonds
3
Ring Count
4
Aromatic Ring Count
2
cLogP
1.58
TPSA
74.57
Fraction CSP3
0.41
Chiral centers
0.0
Largest ring
6.0
QED
0.89
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
antibiotic
Bacterial
Topo II
Topo IV
TOP2A
Apoptosis
Mitochondrial Metabolism
Reactive Oxygen Species (ROS)
Topoisomerase
Antibiotics,Bacterial
Antibiotics,Antineoplastic and Immunosuppressive Antibiotics,Bacterial,Topoisomerase
Reactive Oxygen Species
Indication
otitis
MOA
bacterial DNA gyrase inhibitor
Pathway
Microbiology/virology
Anti-infection
Cell Cycle/DNA Damage
Immunology/Inflammation
Metabolic Enzyme/Protease
NF-κB
NF-¦ÊB
Source data