besifloxacin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antibacterials, nalidixic acid derivatives	4111	141388-76-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: besifloxacin besifloxacin hydrochloride besivance SS734 BOL-303224-A besifloxacin HCl	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. Molecular weight: 393.84 Formula: C19H21ClFN3O3 CLOGP: 0.97 LIPINSKI: 0 HAC: 6 HDO: 2 TPSA: 86.87 ALOGS: -3.44 ROTB: 3 Status: ONP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

besifloxacin
besifloxacin hydrochloride
besivance
SS734
BOL-303224-A
besifloxacin HCl

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.

Molecular weight: 393.84
Formula: C19H21ClFN3O3
CLOGP: 0.97
LIPINSKI: 0
HAC: 6
HDO: 2
TPSA: 86.87
ALOGS: -3.44
ROTB: 3

Status: ONP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

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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

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Approvals:

Date	Agency	Company	Orphan
May 28, 2009	FDA	BAUSCH AND LOMB

FDA Adverse Event Reporting System (Female)

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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	111.40	59.13	17	371	1476	63487158
Corneal infiltrates	83.65	59.13	10	378	132	63488502
Hypopyon	59.57	59.13	9	379	723	63487911
Corneal opacity	59.44	59.13	9	379	734	63487900

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FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

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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	156.26	97.47	25	528	2595	79741240

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	S01AE08	SENSORY ORGANS OPHTHALMOLOGICALS ANTIINFECTIVES Fluoroquinolones
FDA CS	M0023650	Quinolones
FDA EPC	N0000175937	Quinolone Antimicrobial
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D059005	Topoisomerase II Inhibitors
MeSH PA	D059003	Topoisomerase Inhibitors

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Bacterial conjunctivitis	indication	128350005	DOID:9700
Superimposed infection	contraindication	193198003

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🐶 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)

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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

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Topoisomerase IV	Enzyme		PARC_ECOLI PARE_ECOLI	INHIBITOR				CHEMBL	CHEMBL
DNA gyrase	Enzyme		GYRA_ECOLI GYRB_ECOLI	INHIBITOR				CHEMBL	CHEMBL

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External reference:

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ID	Source
013123	NDDF
013124	NDDF
10178705	PUBCHEM_CID
165190	MMSL
26480	MMSL
4028790	VUID
4028790	VANDF
4028791	VANDF
405165-61-9	SECONDARY_CAS_RN
442870007	SNOMEDCT_US

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Pharmaceutical products:

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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	24208-446	SUSPENSION	6 mg	OPHTHALMIC	NDA	22 sections
Besivance	HUMAN PRESCRIPTION DRUG LABEL	1	24208-446	SUSPENSION	6 mg	OPHTHALMIC	NDA	22 sections
Besivance	HUMAN PRESCRIPTION DRUG LABEL	1	50090-1241	SUSPENSION	6 mg	OPHTHALMIC	NDA	22 sections
Besivance	HUMAN PRESCRIPTION DRUG LABEL	1	50090-1241	SUSPENSION	6 mg	OPHTHALMIC	NDA	22 sections
Besivance	HUMAN PRESCRIPTION DRUG LABEL	1	54868-6282	SUSPENSION	6 mg	OPHTHALMIC	NDA	23 sections

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