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besifloxacin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| antibacterials, nalidixic acid derivatives | 4111 | 141388-76-3 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
Besifloxacin is an 8-chloro fluoroquinolone with a N-1 cyclopropyl group. The compound has activity against Gram-positive and Gram-negative bacteria due to the inhibition of both bacterial DNA gyrase and topoisomerase IV. DNA gyrase is an essential enzyme required for replication, transcription and repair of bacterial DNA. Topoisomerase IV is an essential enzyme required for partitioning of the chromosomal DNA during bacterial cell division.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
None
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| fu (Fraction unbound in plasma) | 0.39 % | Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| azlogd74 | LogD at pH 7.4 | -0.076 | High | 0.88 | |
| caco2-efflux | Caco-2 efflux ratio (BA/AB) | 2.979 | High | 0.88 | |
| caco2-intrinsic-papp | Caco-2 intrinsic apparent permeability | 5.346 | 10^-6 cm/s | High | 0.88 |
| dh-clint | Dog hepatocyte intrinsic clearance | 1.274 | uL/min/10^6 cells | High | 0.88 |
| dppb | Dog plasma protein binding (% unbound) | 61.800 | % | High | 0.88 |
| fcs-ppb | Fetal calf serum protein binding (% unbound) | 62.720 | % | High | 0.88 |
| herg | hERG pIC50 | 4.656 | pIC50 | High | 0.88 |
| hh-clint | Human hepatocyte intrinsic clearance | 1.208 | uL/min/10^6 cells | High | 0.88 |
| hlm-clint | Human liver microsomal intrinsic clearance | 3.548 | uL/min/mg protein | High | 0.88 |
| hppb | Human plasma protein binding (% unbound) | 61.260 | % | High | 0.88 |
| kinase-safety-class | EIF2AK3,GRK2,PDK1,PDK2,PDK4 | 5 | |||
| kinase-selectivity-class | AXL,CDK9,DYRK1B,EIF2AK3,GRK2,MAPK7,PRKDC,STK33,TTK | 9 | |||
| mdck-mdr1-efflux | MDCK-MDR1 efflux ratio | 7.311 | High | 0.88 | |
| mh-clint | Mouse hepatocyte intrinsic clearance | 6.081 | High | 0.88 | |
| mppb | Mouse plasma protein binding (% unbound) | 57.880 | High | 0.88 | |
| nih-mdck-mdr1-efflux | NIH MDCK-MDR1 efflux ratio | 15.704 | High | 0.88 | |
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| pppb | Pig plasma protein binding (% unbound) | 72.680 | % | High | 0.88 |
| rh-clint | Rat hepatocyte intrinsic clearance | 1.656 | uL/min/10^6 cells | High | 0.88 |
| rh-fuinc | Rat hepatocyte fraction unbound in incubation | 83.370 | % | High | 0.88 |
| rppb | Rat plasma protein binding (% unbound) | 43.640 | % | High | 0.88 |
| solubility-dd | Solubility at pH 7.4 in DMSO | 847.227 | uM | High | 0.88 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| May 28, 2009 | FDA | BAUSCH AND LOMB |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Corneal oedema | 111.80 | 62.76 | 17 | 407 | 1884 | 90626139 |
| Corneal infiltrates | 84.45 | 62.76 | 10 | 414 | 161 | 90627862 |
FDA Adverse Event Reporting System (Male)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Hypersensitivity | 207.70 | 119.12 | 55 | 248 | 72315 | 42548717 |
| Cardiac disorder | 162.69 | 119.12 | 42 | 261 | 48890 | 42572142 |
FDA Adverse Event Reporting System (Geriatric)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Cardiac disorder | 156.48 | 91.91 | 43 | 587 | 76237 | 110512432 |
| Corneal oedema | 156.32 | 91.91 | 25 | 605 | 3148 | 110585521 |
| Hypersensitivity | 134.01 | 91.91 | 58 | 572 | 403940 | 110184729 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | S01AE08 | SENSORY ORGANS OPHTHALMOLOGICALS ANTIINFECTIVES Fluoroquinolones |
| FDA CS | M0023650 | Quinolones |
| MeSH PA | D000890 | Anti-Infective Agents |
| MeSH PA | D000900 | Anti-Bacterial Agents |
| MeSH PA | D000970 | Antineoplastic Agents |
| MeSH PA | D004791 | Enzyme Inhibitors |
| MeSH PA | D059003 | Topoisomerase Inhibitors |
| MeSH PA | D059005 | Topoisomerase II Inhibitors |
| FDA EPC | N0000175937 | Quinolone Antimicrobial |
| CHEBI has role | CHEBI:33282 | antibacterial agent |
| CHEBI has role | CHEBI:66981 | ophthalmology drug |
| CHEBI has role | CHEBI:49201 | anti-ulcer drug |
Related Drugs by ATC class:
S01AE Fluoroquinolones 8 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| Bacterial conjunctivitis | indication | 128350005 | DOID:9700 |
| Superimposed infection | contraindication | 193198003 |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 6.06 | acidic |
| pKa2 | 9.41 | Basic |
| pKa3 | 2.15 | Basic |
Orange Book patent data (new drug applications)
| Formulation strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Patent number | Patent expiration date | Patent use |
|---|---|---|---|---|---|---|---|---|---|---|
| EQ 0.6% BASE | BESIVANCE | BAUSCH AND LOMB | N022308 | May 28, 2009 | RX | SUSPENSION/DROPS | OPHTHALMIC | 8937062 | Nov. 13, 2029 | METHOD OF TREATING OCULAR BACTERIAL INFECTIONS |
| EQ 0.6% BASE | BESIVANCE | BAUSCH AND LOMB | N022308 | May 28, 2009 | RX | SUSPENSION/DROPS | OPHTHALMIC | 8415342 | Nov. 7, 2030 | METHOD OF TREATING OCULAR BACTERIAL INFECTIONS |
Orange Book exclusivity data (new drug applications)
None
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| Topoisomerase IV | Enzyme | INHIBITOR | CHEMBL | CHEMBL | |||||
| DNA gyrase | Enzyme | INHIBITOR | CHEMBL | CHEMBL |
External reference:
| ID | Source |
|---|---|
| 4028790 | VUID |
| N0000178482 | NUI |
| D08872 | KEGG_DRUG |
| 4028790 | VANDF |
| 4028791 | VANDF |
| C2351042 | UMLSCUI |
| CHEBI:135622 | CHEBI |
| CHEMBL1201760 | ChEMBL_ID |
| CHEMBL1201761 | ChEMBL_ID |
| DB06771 | DRUGBANK_ID |
| C522124 | MESH_SUPPLEMENTAL_RECORD_UI |
| 10178705 | PUBCHEM_CID |
| 12877 | IUPHAR_LIGAND_ID |
| 8958 | INN_ID |
| 405165-61-9 | SECONDARY_CAS_RN |
| BFE2NBZ7NX | UNII |
| 819911 | RXNORM |
| 165190 | MMSL |
| 26480 | MMSL |
| 013123 | NDDF |
| 013124 | NDDF |
| 230471000087100 | SNOMEDCT_US |
| 442870007 | SNOMEDCT_US |
| 442915008 | SNOMEDCT_US |
Pharmaceutical products:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| Besivance | HUMAN PRESCRIPTION DRUG LABEL | 1 | 24208-446 | SUSPENSION | 6 mg | OPHTHALMIC | NDA | 22 sections |
| Besivance | HUMAN PRESCRIPTION DRUG LABEL | 1 | 54868-6282 | SUSPENSION | 6 mg | OPHTHALMIC | NDA | 23 sections |
| Besivance | HUMAN PRESCRIPTION DRUG LABEL | 1 | 82260-466 | SUSPENSION | 6 mg | OPHTHALMIC | NDA | 22 sections |
| Besivance | HUMAN PRESCRIPTION DRUG LABEL | 1 | 85766-257 | SUSPENSION | 6 mg | OPHTHALMIC | NDA | 22 sections |