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Besifloxacin

Besifloxacin structure

CAS No:
141388-76-3
Formula:
C19H21ClFN3O3
Chemical Name:
Besifloxacin
Synonyms:
3-Quinolinecarboxylic acid,7-[(3R)-3-aminohexahydro-1H-azepin-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-;3-Quinolinecarboxylic acid,7-(3-aminohexahydro-1H-azepin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-,(R)-;7-[(3R)-3-Aminohexahydro-1H-azepin-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;Besifloxacin;(R)-(+)-7-(3-Amino-2,3,4,5,6,7-hexahydro-1H-azepin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid;(R)-7-(3-Aminohexahydro-1H-azepin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Yellow to slightly yellow crystalline powder

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

Besifloxacin Basic Attributes

Molecular Weight：

393.844

Exact Mass：

393.84

UNII：

BFE2NBZ7NX

DSSTox ID：

DTXSID00161706

ATC Code：

S - Sensory organs

Characteristics

PSA：

86.9

XLogP3：

1.91

Density：

1.469

Boiling Point：

607.0±55.0 °C(Predicted)

Flash Point：

320.9±31.5 °C

Refractive Index：

1.649

Water Solubility：

Not soluble in water

PKA：

6.0-7.0

Toxicity

Toxicity Summary：

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

Protein Binding：

None

Drug Information

Drug 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*|FDA Label

Pharmacology：

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.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

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.|N/A|Not absorbed into the systemic

Metabolism/Metabolites：

No appreciable metabolism

Biological Half-Life：

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

MeSH Entry Terms：

7-((3R)-aminohexahydro-1H-azepin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Besifloxacin Use and Manufacturing

An amino-azepinyl quinolone formulated as a suspension for ophthalmic usage. It exhibits good antistaphylococcal activity, as well as activity against Str. pneumoniae, Enterobacteriaceae, H. influenzae and Mor. catarrhalis. It is weakly active against Corynebacterium spp. and has no useful activity against Ps. aeruginosa. After instillation into the eye, less than 0.1% of the drug reaches the plasma. It is used for bacterial conjunctivitis.

Computed Properties

Molecular Weight:393.8
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:393.1255474
Monoisotopic Mass:393.1255474
Topological Polar Surface Area:86.9
Heavy Atom Count:27
Complexity:656
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Besifloxacin

CAS No.: 141388-76-3

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