Identification

Name
Besifloxacin
Accession Number
DB06771  (DB05862)
Type
Small Molecule
Groups
Approved
Description

Besifloxacin is a fourth generation fluoroquinolone-type opthalmic antibiotic for the treatment of bacterial conjunctivitis. FDA approved on May 28, 2009.

Structure
Thumb
Synonyms
Not Available
External IDs
ISV-403
Product Ingredients
IngredientUNIICASInChI Key
Besifloxacin hydrochloride7506A6J57T405165-61-9PMQBICKXAAKXAY-HNCPQSOCSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BesivanceSuspension6 mg/1mLOphthalmicA-S Medication Solutions2009-05-28Not applicableUs
BesivanceSuspension0.6 %OphthalmicBausch & Lomb Inc2010-01-27Not applicableCanada
BesivanceSuspension6 mg/1mLOphthalmicBauch & Lomb Incorporated2009-05-28Not applicableUs
BesivanceSuspension6 mg/1mLOphthalmicPhysicians Total Care, Inc.2011-07-13Not applicableUs
Categories
UNII
BFE2NBZ7NX
CAS number
141388-76-3
Weight
Average: 393.84
Monoisotopic: 393.125547465
Chemical Formula
C19H21ClFN3O3
InChI Key
QFFGVLORLPOAEC-SNVBAGLBSA-N
InChI
InChI=1S/C19H21ClFN3O3/c20-15-16-12(18(25)13(19(26)27)9-24(16)11-4-5-11)7-14(21)17(15)23-6-2-1-3-10(22)8-23/h7,9-11H,1-6,8,22H2,(H,26,27)/t10-/m1/s1
IUPAC Name
7-[(3R)-3-aminoazepan-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
SMILES
N[C@@H]1CCCCN(C1)C1=C(F)C=C2C(=O)C(=CN(C3CC3)C2=C1Cl)C(O)=O

Pharmacology

Indication

Treatment of bacterial conjunctivitis. Bacterial isolates that are susceptible to besifloxacin include: CDC coryneform group G; Corynebacterium pseudodiphtheriticum; Corynebacterium striatum; Haemophilus influenzae; Moraxella lacunata; Staphylococcus aureus; Staphylococcus epidermidis; Staphylococcus hominis; Staphylococcus lugdunensis; Streptococcus mitis group; Streptococcus oralis; Streptococcus pneumoniae; Streptococcus salivarius*

Associated Conditions
Pharmacodynamics

Besifloxacin tear concentrations were higher than MIC90 (minimum inhibitory concentration) values for common bacterial pathogens and sustained for 24 hours or longer. Mean residence time in the conjunctiva was 4.7 hours.

Mechanism of action

Besifloxacin is a bactericidal fluroquinolone-type antibiotic that inhibits bacterial enzymes, DNA gyrase and topoisomerase IV. By inhibiting DNA gyrase, DNA replication, transcription, and repair is impaired. By inhibiting topoisomerase IV, decatenation during cell devision is impaired. Inhibiting these two targets also slows down development of resistance.

TargetActionsOrganism
ADNA topoisomerase 4 subunit A
antagonist
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA topoisomerase 4 subunit A
antagonist
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
ADNA gyrase subunit A
antagonist
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA gyrase subunit A
antagonist
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Absorption

Although ocular surface concentrations are high, average systemic concentrtions after three-times daily dosing was less than 0.5 ng/mL. This indicates that besifloxacin is not appreciably absorbed into the systemic and has a very low risk of systemic side effects.

Volume of distribution

Not absorbed into the systemic

Protein binding

None

Metabolism

No appreciable metabolism

Route of elimination

N/A

Half life

The average elimination half-life of besifloxacin in plasma following multiple dosing was estimated to be 7 hours.

Clearance

N/A

Toxicity

LD50, rat: >2000 mg/kg. The most common adverse reaction reported in 2% of patients treated with besifloxacin was conjunctival redness.

Affected organisms
  • Gram negative and gram positive bacteria
  • Pseudomonas aeruginosa
  • Streptococcus pneumoniae
  • Haemophilus influenzae
  • Staphylococcus aureus
  • Aerococcus viridans
  • Corynebacterium sp. G
  • Corynebacterium pseudodiphtheriticum
  • Corynebacterium striatum
  • Moraxella catarrhalis
  • Moraxella lacunata
  • Staphylococcus epidermidis
  • Staphylococcus hominis
  • Staphylococcus lugdunensis
  • Staphylococcus warneri
  • Streptococcus mitis
  • Streptococcus oralis
  • Streptococcus salivarius
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Besifloxacin.Approved, Investigational
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Besifloxacin.Approved, Investigational
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Besifloxacin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Besifloxacin.Experimental
Acetylsalicylic acidAcetylsalicylic acid may increase the neuroexcitatory activities of Besifloxacin.Approved, Vet Approved
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Besifloxacin.Approved, Vet Approved
AmiodaroneThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Amiodarone.Approved, Investigational
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Besifloxacin.Approved, Investigational, Withdrawn
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Besifloxacin.Investigational
Beclomethasone dipropionateThe risk or severity of tendinopathy can be increased when Beclomethasone dipropionate is combined with Besifloxacin.Approved, Investigational
BenzatropineThe risk or severity of QTc prolongation can be increased when Benzatropine is combined with Besifloxacin.Approved
BepridilThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Bepridil.Approved, Withdrawn
BetamethasoneThe risk or severity of tendinopathy can be increased when Betamethasone is combined with Besifloxacin.Approved, Vet Approved
BetaxololThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Betaxolol.Approved, Investigational
BortezomibThe risk or severity of QTc prolongation can be increased when Bortezomib is combined with Besifloxacin.Approved, Investigational
BromocriptineThe therapeutic efficacy of Bromocriptine can be increased when used in combination with Besifloxacin.Approved, Investigational
BrompheniramineThe risk or severity of QTc prolongation can be increased when Brompheniramine is combined with Besifloxacin.Approved
BudesonideThe risk or severity of tendinopathy can be increased when Budesonide is combined with Besifloxacin.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Besifloxacin.Approved
CaffeineThe metabolism of Caffeine can be decreased when combined with Besifloxacin.Approved
Calcium AcetateCalcium Acetate can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Calcium CarbonateCalcium Carbonate can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Calcium ChlorideCalcium Chloride can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CetirizineThe risk or severity of QTc prolongation can be increased when Cetirizine is combined with Besifloxacin.Approved
ChlorphenamineThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Chlorphenamine.Approved
ChlorpromazineThe risk or severity of QTc prolongation can be increased when Chlorpromazine is combined with Besifloxacin.Approved, Investigational, Vet Approved
CinnarizineThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Cinnarizine.Approved, Investigational
CiprofloxacinThe risk or severity of QTc prolongation can be increased when Ciprofloxacin is combined with Besifloxacin.Approved, Investigational
ClemastineThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Clemastine.Approved, Investigational
Clobetasol propionateThe risk or severity of tendinopathy can be increased when Clobetasol propionate is combined with Besifloxacin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Besifloxacin.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Besifloxacin.Experimental
DapagliflozinThe therapeutic efficacy of Dapagliflozin can be increased when used in combination with Besifloxacin.Approved
DelamanidBesifloxacin may increase the QTc-prolonging activities of Delamanid.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Besifloxacin.Approved
DexamethasoneThe risk or severity of tendinopathy can be increased when Dexamethasone is combined with Besifloxacin.Approved, Investigational, Vet Approved
DexbrompheniramineThe risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Besifloxacin.Approved
DiclofenacDiclofenac may increase the neuroexcitatory activities of Besifloxacin.Approved, Vet Approved
DiflunisalDiflunisal may increase the neuroexcitatory activities of Besifloxacin.Approved, Investigational
DigitoxinDigitoxin may decrease the cardiotoxic activities of Besifloxacin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Besifloxacin.Approved
DimenhydrinateThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Dimenhydrinate.Approved
DiphenhydramineThe risk or severity of QTc prolongation can be increased when Diphenhydramine is combined with Besifloxacin.Approved, Investigational
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Besifloxacin.Approved, Investigational
DofetilideThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Dofetilide.Approved, Investigational
DoxepinThe risk or severity of QTc prolongation can be increased when Doxepin is combined with Besifloxacin.Approved, Investigational
DoxylamineThe risk or severity of QTc prolongation can be increased when Doxylamine is combined with Besifloxacin.Approved, Vet Approved
ErythromycinThe risk or severity of QTc prolongation can be increased when Erythromycin is combined with Besifloxacin.Approved, Investigational, Vet Approved
EsmololThe risk or severity of QTc prolongation can be increased when Esmolol is combined with Besifloxacin.Approved
FamotidineThe risk or severity of QTc prolongation can be increased when Famotidine is combined with Besifloxacin.Approved
FluconazoleThe risk or severity of QTc prolongation can be increased when Fluconazole is combined with Besifloxacin.Approved, Investigational
FlunisolideThe risk or severity of tendinopathy can be increased when Flunisolide is combined with Besifloxacin.Approved, Investigational
Fluocinolone acetonideThe risk or severity of tendinopathy can be increased when Fluocinolone Acetonide is combined with Besifloxacin.Approved, Investigational, Vet Approved
FluorometholoneThe risk or severity of tendinopathy can be increased when Fluorometholone is combined with Besifloxacin.Approved, Investigational
FluorouracilThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Fluorouracil.Approved
FluoxetineThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Fluoxetine.Approved, Vet Approved
FlurbiprofenFlurbiprofen may increase the neuroexcitatory activities of Besifloxacin.Approved, Investigational
Fluticasone propionateThe risk or severity of tendinopathy can be increased when Fluticasone propionate is combined with Besifloxacin.Approved
GabapentinThe risk or severity of QTc prolongation can be increased when Gabapentin is combined with Besifloxacin.Approved, Investigational
GanciclovirThe metabolism of Ganciclovir can be decreased when combined with Besifloxacin.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Besifloxacin.Experimental
GlimepirideThe therapeutic efficacy of Glimepiride can be increased when used in combination with Besifloxacin.Approved
GlipizideThe therapeutic efficacy of Glipizide can be increased when used in combination with Besifloxacin.Approved, Investigational
GlyburideThe therapeutic efficacy of Glyburide can be increased when used in combination with Besifloxacin.Approved
GoserelinThe risk or severity of QTc prolongation can be increased when Goserelin is combined with Besifloxacin.Approved
HaloperidolThe risk or severity of QTc prolongation can be increased when Haloperidol is combined with Besifloxacin.Approved
HydrocortisoneThe risk or severity of tendinopathy can be increased when Hydrocortisone is combined with Besifloxacin.Approved, Vet Approved
Hydrocortisone acetateThe risk or severity of tendinopathy can be increased when Hydrocortisone acetate is combined with Besifloxacin.Approved, Vet Approved
Hydrocortisone butyrateThe risk or severity of tendinopathy can be increased when Hydrocortisone butyrate is combined with Besifloxacin.Approved, Vet Approved
HydroxychloroquineThe risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Besifloxacin.Approved
HydroxyzineThe risk or severity of QTc prolongation can be increased when Hydroxyzine is combined with Besifloxacin.Approved
IbandronateThe risk or severity of QTc prolongation can be increased when Ibandronate is combined with Besifloxacin.Approved, Investigational
IbuprofenIbuprofen may increase the neuroexcitatory activities of Besifloxacin.Approved
IcosapentIcosapent may increase the neuroexcitatory activities of Besifloxacin.Approved, Nutraceutical
ImipramineThe risk or severity of QTc prolongation can be increased when Imipramine is combined with Besifloxacin.Approved
IndomethacinIndomethacin may increase the neuroexcitatory activities of Besifloxacin.Approved, Investigational
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be increased when used in combination with Besifloxacin.Approved
Insulin HumanThe therapeutic efficacy of Insulin Human can be increased when used in combination with Besifloxacin.Approved, Investigational
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be increased when used in combination with Besifloxacin.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be increased when used in combination with Besifloxacin.Approved
IsofluraneThe risk or severity of QTc prolongation can be increased when Isoflurane is combined with Besifloxacin.Approved, Vet Approved
IsradipineThe risk or severity of QTc prolongation can be increased when Isradipine is combined with Besifloxacin.Approved, Investigational
ItraconazoleThe risk or severity of QTc prolongation can be increased when Itraconazole is combined with Besifloxacin.Approved, Investigational
KetoprofenKetoprofen may increase the neuroexcitatory activities of Besifloxacin.Approved, Vet Approved
KetorolacKetorolac may increase the neuroexcitatory activities of Besifloxacin.Approved
KetotifenThe risk or severity of QTc prolongation can be increased when Ketotifen is combined with Besifloxacin.Approved
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Besifloxacin.Experimental
LeuprolideThe risk or severity of QTc prolongation can be increased when Leuprolide is combined with Besifloxacin.Approved, Investigational
LevocabastineThe risk or severity of QTc prolongation can be increased when Levocabastine is combined with Besifloxacin.Approved, Investigational
LoratadineThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Loratadine.Approved, Investigational
Magnesium hydroxideMagnesium hydroxide can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Magnesium sulfateMagnesium sulfate can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational, Vet Approved
MepyramineThe risk or severity of QTc prolongation can be increased when Mepyramine is combined with Besifloxacin.Approved, Vet Approved
MetforminThe therapeutic efficacy of Metformin can be increased when used in combination with Besifloxacin.Approved
MethotrimeprazineThe risk or severity of QTc prolongation can be increased when Methotrimeprazine is combined with Besifloxacin.Approved, Investigational
MethylprednisoloneThe risk or severity of tendinopathy can be increased when Methylprednisolone is combined with Besifloxacin.Approved, Vet Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Besifloxacin.Experimental
MetoclopramideThe risk or severity of QTc prolongation can be increased when Metoclopramide is combined with Besifloxacin.Approved, Investigational
MetronidazoleThe risk or severity of QTc prolongation can be increased when Metronidazole is combined with Besifloxacin.Approved
Mometasone furoateThe risk or severity of tendinopathy can be increased when Mometasone furoate is combined with Besifloxacin.Approved, Vet Approved
MoxifloxacinThe risk or severity of QTc prolongation can be increased when Moxifloxacin is combined with Besifloxacin.Approved, Investigational
NaproxenNaproxen may increase the neuroexcitatory activities of Besifloxacin.Approved, Vet Approved
NicardipineThe risk or severity of QTc prolongation can be increased when Nicardipine is combined with Besifloxacin.Approved, Investigational
NimesulideNimesulide may increase the neuroexcitatory activities of Besifloxacin.Approved, Investigational, Withdrawn
NortriptylineThe risk or severity of QTc prolongation can be increased when Nortriptyline is combined with Besifloxacin.Approved
OctreotideThe risk or severity of QTc prolongation can be increased when Octreotide is combined with Besifloxacin.Approved, Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Besifloxacin.Experimental, Investigational
OndansetronThe risk or severity of QTc prolongation can be increased when Ondansetron is combined with Besifloxacin.Approved
OrphenadrineThe risk or severity of QTc prolongation can be increased when Orphenadrine is combined with Besifloxacin.Approved
OuabainOuabain may decrease the cardiotoxic activities of Besifloxacin.Approved
OxytocinThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Besifloxacin.Approved, Vet Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Besifloxacin.Approved, Vet Approved
PapaverineThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Papaverine.Approved, Investigational
ParoxetineThe risk or severity of QTc prolongation can be increased when Paroxetine is combined with Besifloxacin.Approved, Investigational
PeruvosidePeruvoside may decrease the cardiotoxic activities of Besifloxacin.Experimental
PheniramineThe risk or severity of QTc prolongation can be increased when Pheniramine is combined with Besifloxacin.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Besifloxacin.Approved
PrednisoloneThe risk or severity of tendinopathy can be increased when Prednisolone is combined with Besifloxacin.Approved, Vet Approved
PromethazineThe risk or severity of QTc prolongation can be increased when Promethazine is combined with Besifloxacin.Approved, Investigational
PropafenoneThe risk or severity of QTc prolongation can be increased when Propafenone is combined with Besifloxacin.Approved
PropranololThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Propranolol.Approved, Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Besifloxacin.Experimental
QuetiapineThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Quetiapine.Approved
QuinaprilQuinapril can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
RisperidoneThe risk or severity of QTc prolongation can be increased when Risperidone is combined with Besifloxacin.Approved, Investigational
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be increased when used in combination with Besifloxacin.Approved, Investigational
SalbutamolThe risk or severity of QTc prolongation can be increased when Salbutamol is combined with Besifloxacin.Approved, Vet Approved
Salicylic acidSalicylic acid may increase the neuroexcitatory activities of Besifloxacin.Approved, Investigational, Vet Approved
SalmeterolThe risk or severity of QTc prolongation can be increased when Salmeterol is combined with Besifloxacin.Approved
SaxagliptinThe therapeutic efficacy of Saxagliptin can be increased when used in combination with Besifloxacin.Approved
SertralineThe risk or severity of QTc prolongation can be increased when Sertraline is combined with Besifloxacin.Approved
SitagliptinThe therapeutic efficacy of Sitagliptin can be increased when used in combination with Besifloxacin.Approved, Investigational
SucralfateSucralfate can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SulfasalazineSulfasalazine may increase the neuroexcitatory activities of Besifloxacin.Approved
SulindacSulindac may increase the neuroexcitatory activities of Besifloxacin.Approved, Investigational
TamoxifenThe risk or severity of QTc prolongation can be increased when Tamoxifen is combined with Besifloxacin.Approved
TerbutalineThe risk or severity of QTc prolongation can be increased when Terbutaline is combined with Besifloxacin.Approved
TerodilineThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Terodiline.Experimental
Tolfenamic AcidTolfenamic Acid may increase the neuroexcitatory activities of Besifloxacin.Approved, Investigational
TrazodoneThe risk or severity of QTc prolongation can be increased when Trazodone is combined with Besifloxacin.Approved, Investigational
TriamcinoloneThe risk or severity of tendinopathy can be increased when Triamcinolone is combined with Besifloxacin.Approved, Vet Approved
TrimethoprimThe risk or severity of QTc prolongation can be increased when Trimethoprim is combined with Besifloxacin.Approved, Vet Approved
TrimipramineThe risk or severity of QTc prolongation can be increased when Trimipramine is combined with Besifloxacin.Approved
Trolamine salicylateTrolamine salicylate may increase the neuroexcitatory activities of Besifloxacin.Approved
UlobetasolThe risk or severity of tendinopathy can be increased when Ulobetasol is combined with Besifloxacin.Approved
ValaciclovirThe metabolism of Valaciclovir can be decreased when combined with Besifloxacin.Approved, Investigational
Valproic AcidThe risk or severity of QTc prolongation can be increased when Besifloxacin is combined with Valproic Acid.Approved, Investigational
VenlafaxineThe risk or severity of QTc prolongation can be increased when Venlafaxine is combined with Besifloxacin.Approved
WarfarinThe therapeutic efficacy of Warfarin can be increased when used in combination with Besifloxacin.Approved
ZincZinc can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Zinc acetateZinc acetate can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Zinc chlorideZinc chloride can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Zinc oxideZinc oxide can cause a decrease in the absorption of Besifloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Food Interactions
Not Available

References

General References
  1. O'Brien TP: Besifloxacin ophthalmic suspension, 0.6%: a novel topical fluoroquinolone for bacterial conjunctivitis. Adv Ther. 2012 Jun;29(6):473-90. doi: 10.1007/s12325-012-0027-7. Epub 2012 Jun 20. [PubMed:22729919]
  2. Proksch JW, Granvil CP, Siou-Mermet R, Comstock TL, Paterno MR, Ward KW: Ocular pharmacokinetics of besifloxacin following topical administration to rabbits, monkeys, and humans. J Ocul Pharmacol Ther. 2009 Aug;25(4):335-44. doi: 10.1089/jop.2008.0116. [PubMed:19492955]
External Links
KEGG Drug
D08872
PubChem Compound
10178705
PubChem Substance
175427091
ChemSpider
8354210
ChEBI
135622
ChEMBL
CHEMBL1201760
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Besifloxacin
ATC Codes
S01AE08 — Besifloxacin
AHFS Codes
  • 52:04.04 — Antibacterials
FDA label
Download (148 KB)
MSDS
Download (159 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedScreeningCataract Extraction1
1CompletedScreeningHealthy Volunteers2
1CompletedTreatmentConjunctivitis, Bacterial1
2CompletedTreatmentConjunctivitis, Bacterial1
2TerminatedTreatmentUlcerative keratitis1
2, 3CompletedTreatmentConjunctivitis, Bacterial1
3CompletedTreatmentAcute Bacterial Conjunctivitis2
3CompletedTreatmentConjunctivitis, Bacterial1
3RecruitingTreatmentKeratitis; Infectious Disease (Manifestation)1
3TerminatedTreatmentConjunctivitis, Bacterial2
4CompletedNot AvailableCataract operation / Corneal Health1
4CompletedOtherCataract Extraction1
4CompletedTreatmentBacterial blepharitis1
4Unknown StatusPreventionCataracts1
Not AvailableRecruitingTreatmentBacterial Keratitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SuspensionOphthalmic0.6 %
SuspensionOphthalmic6 mg/1mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6685958No2004-02-032021-06-20Us
US6699492No2004-03-022019-03-31Us
US5447926No1995-09-052012-09-05Us
US8415342No2010-11-072030-11-07Us
US8937062No2009-11-132029-11-13Us
US8481526No2011-01-092031-01-09Us
US8604020No2010-03-122030-03-12Us

Properties

State
Liquid
Experimental Properties
PropertyValueSource
water solubilityNot soluble in water MSDS
pKa6.0-7.0MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.143 mg/mLALOGPS
logP0.7ALOGPS
logP0.54ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)5.64ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.87 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity101.75 m3·mol-1ChemAxon
Polarizability39 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9882
Blood Brain Barrier-0.9103
Caco-2 permeable-0.5689
P-glycoprotein substrateSubstrate0.8063
P-glycoprotein inhibitor INon-inhibitor0.8968
P-glycoprotein inhibitor IINon-inhibitor0.9584
Renal organic cation transporterNon-inhibitor0.7016
CYP450 2C9 substrateNon-substrate0.869
CYP450 2D6 substrateNon-substrate0.8319
CYP450 3A4 substrateNon-substrate0.6463
CYP450 1A2 substrateNon-inhibitor0.7511
CYP450 2C9 inhibitorNon-inhibitor0.8486
CYP450 2D6 inhibitorNon-inhibitor0.8295
CYP450 2C19 inhibitorNon-inhibitor0.7648
CYP450 3A4 inhibitorNon-inhibitor0.6834
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8053
Ames testAMES toxic0.742
CarcinogenicityNon-carcinogens0.8853
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3263 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9278
hERG inhibition (predictor II)Non-inhibitor0.6497
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
Fluoroquinolones / Chloroquinolines / Aminoquinolines and derivatives / Hydroquinolones / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Azepanes / Aryl chlorides / Benzenoids
show 14 more
Substituents
Quinoline-3-carboxylic acid / Fluoroquinolone / Aminoquinoline / Dihydroquinolone / Chloroquinoline / Haloquinoline / Dihydroquinoline / Pyridine carboxylic acid or derivatives / Pyridine carboxylic acid / Dialkylarylamine
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Antagonist
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
Gene Name
parC
Uniprot ID
P43702
Uniprot Name
DNA topoisomerase 4 subunit A
Molecular Weight
83366.24 Da
References
  1. Carter NJ, Scott LJ: Besifloxacin ophthalmic suspension 0.6%. Drugs. 2010;70(1):83-97. doi: 10.2165/11203820-000000000-00000. [PubMed:20030427]
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Yes
Actions
Antagonist
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
Gene Name
parC
Uniprot ID
P72525
Uniprot Name
DNA topoisomerase 4 subunit A
Molecular Weight
93132.2 Da
References
  1. Carter NJ, Scott LJ: Besifloxacin ophthalmic suspension 0.6%. Drugs. 2010;70(1):83-97. doi: 10.2165/11203820-000000000-00000. [PubMed:20030427]
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Antagonist
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
Gene Name
gyrA
Uniprot ID
P43700
Uniprot Name
DNA gyrase subunit A
Molecular Weight
97817.145 Da
References
  1. Carter NJ, Scott LJ: Besifloxacin ophthalmic suspension 0.6%. Drugs. 2010;70(1):83-97. doi: 10.2165/11203820-000000000-00000. [PubMed:20030427]
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Yes
Actions
Antagonist
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
Gene Name
gyrA
Uniprot ID
P72524
Uniprot Name
DNA gyrase subunit A
Molecular Weight
92052.595 Da
References
  1. Carter NJ, Scott LJ: Besifloxacin ophthalmic suspension 0.6%. Drugs. 2010;70(1):83-97. doi: 10.2165/11203820-000000000-00000. [PubMed:20030427]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da

Drug created on September 14, 2010 10:21 / Updated on September 17, 2018 20:58