ChemicalBook CAS DataBase List 405165-61-9

405165-61-9

Name	Besifloxacin hydrochloride
CAS	405165-61-9
EINECS(EC#)	696-612-6
Molecular Formula	C19H21ClFN3O3.ClH
MDL Number	MFCD14636632
Molecular Weight	430.305
MOL File	405165-61-9.mol

Synonyms

Unii-7506A6J57t Besifloxacin HCl Hydrochloric Besifloxacin 7-[(3R)-3-AMinohexahydro- Becifloxacin Hydrochloride Besifloxacin hydrochloride Besifloxacin HCl (Besivance) BESIFLOXACIN HCL INTERMEDIATES Besifloxacin hydrochloride, >=98% (R)-7-(3-aMinoazepan-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride (R)-7-(3-AMinohexahydro-1H-azepin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinolin-3-carboxylic acid HCl (R)-7-(3-Aminohexahydro-1H-azepin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride 7-[(3R)-3-AMinohexahydro-1H-azepin-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Hydrochloride 3-Quinolinecarboxylic acid, 7-[(3R)-3-aminohexahydro-1H-azepin-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-, hydrochloride (1:1) 3-Quinolinecarboxylic acid, 7-[(3R)-3-aMinohexahydro-1H-azepin-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-, Monohydrochloride (9CI)

Chemical Properties

Melting point	>210°C (dec.)
storage temp.	Refrigerator
solubility	Methanol (Slightly, Heated, Sonicated), Water (Slightly, Heated, Sonicated)
form	Solid
color	Off-White to Light Beige
InChI	InChI=1/C19H21ClFN3O3.ClH/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);1H/t10-;/s3
InChIKey	PMQBICKXAAKXAY-MEQOOBBNNA-N
SMILES	ClC1C(N2CCCC[C@@H](N)C2)=C(F)C=C2C(=O)C(C(=O)O)=CN(C3CC3)C=12.Cl \|&1:8,r\|

Hazard Information

Chemical Properties

Pale Yellow Solid

Uses

A Fluoroquinolone antibiotic.

Uses

Besifloxacin HCl is a fourth-generation fluoroquinolone antibiotic

Description

Besifloxacin is a new fluoroquinolone antibacterial for ophthalmic use. It is indicated for the treatment of bacterial conjunctivitis, one of the most common ocular infections encountered in the primary care setting. Although the previously marketed fluoroquinolones ciprofloxacin, levofloxacin, ofloxacin, gatifloxacin, and moxifloxacin have been widely used to treat bacterial conjunctivitis, their continued utility is hampered by the emergence of resistance among key ocular isolates such as Staphylococcus aureus. Besifloxacin is the first fluoroquinolone developed exclusively for topical ophthalmic use. Unlike the previously marketed fluoroquinolones, besifloxacin has not been used systemically and is not in development as a systemic agent. Its exclusive indication as a topical agent is expected to reduce the overall environmental exposure of bacteria to besifloxacin, which may contribute to a lower risk for the emergence of bacterial resistance. Fluoroquinolones derive their antibacterial activity via inhibition of two essential bacterial enzymes, DNA gyrase and topoisomerase IV, which regulate processes of DNA replication. Besifloxacin inhibits DNA gyrase and topoisomerase IV from Streptococcus pneumoniae (IC50 = 1 and 0.4 mg/ L, respectively) and Escherichia coli (IC50 = 1 and 10 mg/L, respectively).

Originator

SSP Co. Ltd. (Japan) (Japan)

Brand name

Besivance

Side effects

The most common adverse event reported in patients treated with besifloxacin ophthalmic suspension was conjunctival redness. Other less common adverse events were blurred vision, eye pain, eye irritation, eye pruritus, and headache.

Synthesis

Besifloxacin is a fourth-generation fluoroquinolone antibiotic which is marketed as besifloxacin hydrochloride. It was originally developed by the Japanese firm SSP Co. Ltd and designated SS734. SSP then licensed U.S. and European rights of SS734 for ophthalmic use to InSite Vision, Inc., in 2000, who then developed an eye drop formulation (ISV-403) and conducted preliminary clinical trials before selling the product and all rights to Bausch & Lomb in 2003. The eye drop was approved by the United States Food and Drug Administration (FDA) on May 29, 2009 and marketed under the trade name Besivance. Besifloxacin has been found to inhibit production of pro-inflammatory cytokines in vitro. The synthesis of besifloxacin commences with commercially available ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate.Condensation of this ketoester with triethyl orthoformate resulted in a mixture of vinylogous esters 14. Substitution with cyclopropanamine converts 14 to the vinylogous amide 15 as an unreported distribution of cis- and trans-isomers. This mixture was treated with base at elevated temperature to give 16. Presumably, the trans-isomer isomerizes to the cis-isomer, which subsequently undergoes an intramolecular nucleophilic aromatic substitution with concomitant saponification to construct quinolone acid 16. Quinolone 16 is then subjected to another nucleophilic substitution involving readily available iminoazepine 17 and the displacement reaction proceeds regioselectively to furnish the atomic framework of besifloxacin (18). Acidic methanolysis of 18 at elevated temperature gave besiflozacin (III).

Synthesis_405165-61-9

Questions And Answer

Outline
Besifloxacin hydrochloride is developed by Bausch & Lomba as a new type of fluoroquinolones for the treatment of bacterial conjunctivitis (a non-viral caused infectious purulent eye irritation conjunctivitis ). Bacterial conjunctivitis which is a contagious eye disease, is a common disease that affects people of all ages. The clinical symptoms of infested eye including: foreign body sensation, burning sensation, tearing; conjunctival hyperemia, mucus or purulent discharge; eyelid edema, conjunctival edema and subconjunctival hemorrhage may occur in severe cases . ;
Besifloxacin hydrochloride ophthalmic suspension
Besifloxacin hydrochloride ophthalmic suspension (Besivance) is a fluoroquinolone drug recently approved for the topical treatment of bacterial conjunctivitis. This medicine can quickly kill common pathogens causing conjunctivitis , that is coagulase-negative staphylococci, Streptococcus pneumoniae, Staphylococcus aureus , Haemophilus influenzae bacteria, and other less common bacteria.. Besifloxacin is an effective drug to the Gram-positive and Gram-negative pathogens, include other fluoroquinolone-resistant bacteria , also it can balance the DNA gyrase and topoisomerase IV activity, slow the development of resistance. Topical administration can achieve stable and lasting high concentrations in human tears , and penetration in animal ocular tissue is good, showing excellent safety.
Pharmacokinetic and pharmacodynamic characteristics of Besifloxacin meet the criteria for successfully clearing most Gram-positive and Gram-negative bacteria, while exhibiting minimal systemic exposure.Besifloxacin biochemical properties, pharmacokinetics targeted to achieve/pharmacodynamic objectives and limited to local ophthalmic drug will slow the development of bacterial resistance, making Besifloxacin become attractive choice for acute bacterial conjunctivitis treatment.
The above information is edited by the chemicalbook of Tian Ye. ;

Spectrum Detail

Supplier

Hangzhou Kehui Pharmaceutical Co.,Ltd

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Websitehttp://www.hzkehuipharma.com

HANGZHOU YOUHELIN PHARMTECH CO.LTD

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Hangzhou LinghepharmTechnology Co.,Ltd.

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Shandong Kehui Pharmaceutical Co. LTD

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Shanghai Boyle Chemical Co., Ltd.

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J & K SCIENTIFIC LTD.

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Meryer (Shanghai) Chemical Technology Co., Ltd.

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Chembest Research Laboratories Limited

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Nanjing Chemlin Chemical Co., Ltd

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Chemsky（shanghai）International Co.,Ltd.

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Nanjing Vital Chemical Co., Ltd.

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Dalian Meilun Biotech Co., Ltd.

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Nanjing JinruiJiuAn Biotechnology Co., Ltd.

Telephone025-58196018 800028039

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Shanghai T&W Pharmaceutical Co., Ltd.

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Websitehttp://www.trustwe.com

Haoyuan Chemexpress Co., Ltd.

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Websitehttp://gb.chemexpress.com.cn

Shanghai Aladdin Bio-Chem Technology Co.,LTD

Telephone400-6206333 13167063860

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Shanghai Witofly Chemical Co.,Ltd

Telephone

Websitehttp://www.witofly.com

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405165-61-9

Chemical Properties

Hazard Information

Chemical Properties

Uses

Uses

Description

Originator

Brand name

Side effects

Synthesis

Questions And Answer

Outline

Besifloxacin hydrochloride ophthalmic suspension

Spectrum Detail

Supplier

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