ChemicalBook > CAS DataBase List > Sitafloxacin Sesquihydrate

Sitafloxacin Sesquihydrate

Product Name
Sitafloxacin Sesquihydrate
CAS No.
163253-35-8
Chemical Name
Sitafloxacin Sesquihydrate
Synonyms
Sitafloxacin hydrate;DU 6859;DU-6859;Du 6859a;LS-184401;Sitafloxacin;SITAFLOXACIN;Sitafloxacin;Xitafloxacin;Unii-9td681796g
CBNumber
CB01429828
Molecular Formula
C19H20ClF2N3O4
Formula Weight
427.83
MOL File
163253-35-8.mol
More
Less

Sitafloxacin Sesquihydrate Property

Melting point:
145-147°C (dec.)
alpha 
589 -199.9°
storage temp. 
Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility 
Aqueous Base (Slightly), DMSO (Slightly), Methanol (Very Slightly, Heated)
form 
Solid
color 
White to Off-White
Stability:
Hygroscopic
InChIKey
ANCJYRJLOUSQBW-UWQPBFEBNA-N
SMILES
N[C@@H]1CN(C2=C(C=C3C(=O)C(C(=O)O)=CN([C@@H]4C[C@@H]4F)C3=C2Cl)F)CC21CC2.O |&1:1,16,18,r|
CAS DataBase Reference
163253-35-8(CAS DataBase Reference)
More
Less

Safety

HS Code 
2941900000
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

TRC
Product number
S490920
Product name
SitafloxacinSesquihydrate
Packaging
10mg
Price
$340
Updated
2021/12/16
Usbiological
Product number
020963
Product name
Sitafloxacin Sesquihydrate
Packaging
5mg
Price
$496
Updated
2021/12/16
Usbiological
Product number
289151
Product name
Sitafloxacin sesquihydrate
Packaging
2mg
Price
$515
Updated
2021/12/16
ChemScene
Product number
CS-2489
Product name
Sitafloxacin(hydrate)
Purity
≥98.0%
Packaging
50mg
Price
$290
Updated
2021/12/16
Biorbyt Ltd
Product number
orb134391
Product name
Sitafloxacin hydrate
Purity
>99%
Packaging
100mg
Price
$510
Updated
2021/12/16
More
Less

Sitafloxacin Sesquihydrate Chemical Properties,Usage,Production

Description

The fluoroquinolone antibacterial agent sitafloxacin hydrate was developed by Daiichi Sankyo and was approved and launched last year in Japan. Sitafloxacin’s mode of action is through inhibition of DNA gyrase and topoisomerase IV. It is indicated for the treatment of inflammatory infections such as laryngopharyngitis, adenoiditis, acute bronchitis, pneumonia, secondary infections due to chronic respiratory lesions, cystitis, pyelonephritis, urethritis, cervicitis, otitismedia, sinusitis, periodontitis, and pericoronitis and jaw inflammation. Due to its broad spectrum of potent antibacterial activity, sitafloxacin is expected to be clinically effective in treating severe cases of bacterial infection, relapse/recrudescence of infection and infections in which resistant bacteria are suspected to be the cause.

Chemical Properties

Off-White Solid

Uses

Antibacterial

Uses

Sitafloxacin is a new-generation, broad-spectrum oral fluoroquinolone antibiotic. It is very active against many Gram-positive, Gram-negative and anaerobic clinical isolates, including strains resistant to other fluoroquinolones, was recently approved in

Side effects

The most commonly reported adverse reactions include rash, dizziness, headache, diarrhea, loose stool, stomach discomfort, abdominal bloating, abdominal pain, constipation, indigestion, nausea and stomatitis.

Synthesis

The optically pure fluorocyclopropylamine 111 intermediate was prepared as described in thescheme. Condensation of diphenylmethyl amine 104 with acetaldehyde followed by treatment with trichloromethyl chloroformate in the presence of triethylamine gave N-vinyl carbamoyl chloride 105 in 53% yield. This intermediate was reacted with sodium benzyloxide (generated in situ) to afford N-vinylcarbamate 106 in 82% yield. Fluorocyclopropanation of 106 with zinc¨C monofluorocarbenoid generated from fluorodiiodomethane and diethylzinc provided N-(2-fluorocyclopropyl)carbamate 107 in 90% yield and with a diastereomeric ratio of 93:7 favoring the cis-isomer. Hydrogenolysis of the CBz and the diphenylmethyl groups was accomplished with catalytic 10% palladium on charcoal and was followed by treatment with TsOH to afford dl-108 as its tosylate salt. Acylation of dl- 108 TsOH with l-menthyl chloroformate gave a 1:1 mixture of the diastereomeric carbamate 109 which upon four repeated recrystallizations from hexane/ethyl acetate afforded optically pure 110 in 26% yield. Acidic hydrolysis of 110 furnished 111 as its HCl salt in 88% yield.

Mode of action

Sitafloxacin inhibits DNA gyrase and topoisomerase IV. These enzymes are involved in bacteria DNA replication, transcription, repair, and recombination. Sitafloxacin has less activity against human topoisomerase II, an enzyme involved in cell growth. According to Akasaka et al. DNA gyrase, consisting of the subunits GyrA and GyrB, has ATP-dependent DNA supercoil-ing activity and is a primary target of quinolones in Gram-negative species, such as Escherichia coli and Neisseria gonorrhoeae. In contrast, topoisomerase IV, consisting of the subunits ParC and ParE, has an essential role in partitioning replicated chromosomes and is more sensitive than DNA gyrase to some quinolones, such as levofloxacin and ciprofloxacin in the Gram-positive species, such as Staphylococcus aureus and Streptococcus pneumoniae[1].

References

[1] Ghebremedhin, B. “Bacterial Infections in the Elderly Patient: Focus on Sitafloxacin.” 2012. 0.

Sitafloxacin Sesquihydrate Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Sitafloxacin Sesquihydrate Suppliers

Suzhou Chukai PharmaTech
Tel
0512-88812066 15062531973;
Fax
86-512-63926099
Email
wenlongfcb@qq.com
Country
China
ProdList
111
Advantage
62
EnliPharma Technology Co., Ltd
Tel
0551-66399836 18955197623
Email
sales@enlipharma.com
Country
China
ProdList
1874
Advantage
55
Nanjing hongshenghuo Biotechnology Co., Ltd
Tel
025-58311670 18020159086
Email
54604129@qq.com
Country
China
ProdList
180
Advantage
58
Shanghai Aladdin Biochemical Technology Co.,Ltd.
Tel
+86-18521732826
Email
market@aladdin-e.com
Country
China
ProdList
48461
Advantage
58
Wuhan Dingxintong Pharmaceutical Co. , Ltd.
Tel
027-83984790 17720532645
Fax
027-83984790
Email
t17720532645@163.com
Country
China
ProdList
983
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
021-50182298 021-50180596
Fax
+86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2208
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078
Fax
86-021-50426522,50426273
Email
sales@jingyan-chemical.com
Country
China
ProdList
9976
Advantage
60
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
Advantage
59
More
Less

View Lastest Price from Sitafloxacin Sesquihydrate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Sitafloxacin 163253-35-8
Price
US $0.00/KG
Min. Order
1KG
Purity
99%min
Supply Ability
100kg
Release date
2021-09-13
Hebei Weibang Biotechnology Co., Ltd
Product
Sitafloxacin 163253-35-8
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10mt
Release date
2024-10-29
Hebei Mojin Biotechnology Co.,Ltd
Product
Sitafloxacin Sesquihydrate 163253-35-8
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
50000KG/month
Release date
2024-06-03

163253-35-8, Sitafloxacin SesquihydrateRelated Search:


  • Sitafloxacin hydrate
  • Sitafloxacin Sesquihydrate
  • 7-[(7S)-7-Amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrate (2:3)
  • Sitafloxacin
  • 3-Quinolinecarboxylic acid, 7-((7S)-7-amino-5-azaspiro(24)hept-5-yl)-8-chloro-6-fluoro-1-((1R,2S)-2-fluorocyclopropyl)-1,4-dihydro-4-oxo-, hydrate (2:3)
  • 3-Quinolinecarboxylic acid, 7-(7-amino-5-azaspiro(24)hept-5-yl)-8-chloro-6-fluoro-1-(2-fluorocyclopropyl)-1,4-dihydro-4-oxo-, hydrate (2:3), (1R-(1alpha(S*),2alpha))-
  • Du 6859a
  • Unii-9td681796g
  • Sitafloxacin hydrate (2:3)
  • 7-[(7S)-7-AMino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Hydrate
  • 7-(7-amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro-6-fluoro-1-(2-fluorocyclopropyl)-4-oxo-3-quinolinecarboxylic acid hydrate
  • DU 6859
  • DU 6859A; DU 6859; DU-6859; LS-184401
  • DU-6859
  • LS-184401
  • Sitafloxacin Impurity 24
  • sitafloxacin hydrate Impurity 24
  • 7-[(4S)-4-amino-6-azaspiro[2.4]heptan-6-yl]-8-chloro-6-fluoro-1-[(2S)-2-fluorocyclopropyl]-4-oxo-quinoline-3-carboxylic acid hydrate
  • 7-((S)-7-amino-5-azaspiro
  • DU6859a hydrate
  • 7-((S)-7-Amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro-6-fluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid Sesquihydrate
  • SITAFLOXACIN USP/EP/BP
  • Sitafloxacin 1.5Hydrate (DU6859a)
  • 7-((S)-7-amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro-6-fluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrate
  • 3-Quinolinecarboxylic acid, 7-[(7S)-7-amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-, hydrate (2:3) (9CI, ACI)
  • 7-[(7S)-7-amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-Quinolinecarboxylic acid hydrate (2:3) (9CI ACI)
  • 7-(7S)-7-Amino-5-azaspiro2.4hept-5-yl-8-chloro-6-fluoro-1-(1R,2S)-2-fluoro-cyclopropyl-1,4-dihydro-4-oxo-quinolin-3-carboxylic acid hydrate (2:3)
  • SITAFLOXACIN
  • Sitafloxacin
  • Xitafloxacin
  • DU-6859a|||DU6859a hydrate
  • 163253-35-8
  • C19H20ClF2N3O4
  • C19H18ClF2N3O315H2O
  • 2C19H18ClF2N3O33H2O
  • C19H18ClF2N3O3H2O
  • C19H18ClF2N3O332H2O
  • DU 6859A, DU 6859, DU-6859, LS-184401
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Inhibitors