127254-12-0 Usage
Description
Different sources of media describe the Description of 127254-12-0 differently. You can refer to the following data:
1. Sitafloxacin (Trade name: Gracevit in Japan) belongs to a new generation, broad-spectrum oral fluoroquinolone antibiotics. It is highly active against various kinds of gram-negative, gram-positive and anaerobic clinical isolates, even including strains that are resistant to other kinds of fluoroquinolone antibiotics. It has been listed in Japan for the treatment of respiratory and urinary tract infections. It also shows potential for the treatment of Buruli ulcer. Its mechanism of action is through inhibiting the Topoisomerase II ligase domain of bacteria, causing DNA fragmentation to inhibit the DNA synthesis of bacteria.
2. Sitafloxacin hydrate is the newest member (fourth generation) of the fluoroquinolone family of antibiotics that exhibits broad spectrum activity against many Gram-positive, Gramnegative, and anaerobic clinical isolates, including strains resistant to other fluoroquinolones. Since the launch of the first fluoroquinolone norfloxacin (patented in 1978), 20 other versions have made it to market with ciprofloxacin and levofloxacin experiencing the most prevalent usage. The mechanism of action involves inhibition of bacterial type II topoisomerases, both DNA gyrase and topoisomerase IV. By inhibiting these enzymes and preventing DNA supercoiling, cell division is disrupted leading to cell death. In Gram-negative bacteria, the primary target appears to be gyrase, whereas topoisomerase IV is involved in Gram-positive bacteria. Dual inhibition is attractive for widespread activity and avoidance of resistance as both encoding genes would have to acquire mutations.
References
http://www.biochempartner.com/product_details.aspx?item_id=6084
https://en.wikipedia.org/wiki/Sitafloxacin
Originator
Daiichi Sankyo (Japan)
Uses
Antibacterial (DNA-gyrase inhibitor).
Brand name
Gracevit
Pharmaceutical Applications
A group 4 quinolone formulated for oral or intravenous use. In-vitro activity is similar to or better than that of moxifloxacin. The antibacterial spectrum covers Gram-positive and Gram-negative bacteria including anaerobes. It has a chlorine atom at the C-8 position, and therefore has potential for phototoxicity. Early interest in this compound has not been maintained, but it is available in Japan.
Side effects
As a class, the major adverse events for fluoroquinolones are cardiac arrhythmia (due to QT interval 622 Shridhar Hegde and Michelle Schmidt prolongation), major phototoxicity, CNS disturbances (seizures, dizziness, and headaches), and tendonitis. The GI side effects, common to most antimicrobials, include Clostridium difficile-associated diarrhea (CDAD) and alterations in glucose homeostasis. From the clinical safety profile of sitafloxacin (1,059 patients receiving either 50 mg b.i.d. or 100 mg b.i.d.), about a third of patients experienced an adverse event with the most common being diarrhea, liver enzyme elevations, and headaches; however, the risk of QT prolongation, hypoglycemia, and hepatotoxicity were all considered to be low. Phototoxicity appears to be the limiting toxicity, particularly in non-Asian patients.
Check Digit Verification of cas no
The CAS Registry Mumber 127254-12-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,7,2,5 and 4 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 127254-12:
(8*1)+(7*2)+(6*7)+(5*2)+(4*5)+(3*4)+(2*1)+(1*2)=110
110 % 10 = 0
So 127254-12-0 is a valid CAS Registry Number.
InChI:InChI=1/C19H18ClF2N3O3/c20-14-15-8(17(26)9(18(27)28)5-25(15)12-4-10(12)21)3-11(22)16(14)24-6-13(23)19(7-24)1-2-19/h3,5,10,12-13H,1-2,4,6-7,23H2,(H,27,28)/t10-,12+,13+/m0/s1
127254-12-0Relevant articles and documents
Preparation method of sitafloxacin hydrate
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, (2019/02/04)
The invention discloses a preparation method of sitafloxacin hydrate. The method comprises the following steps: taking ethyl 4-bromoacetoacetate used as a raw material, enabling ethyl 4-bromoacetoacetate to be fully reacted with 1,2-dibromoethane and preparing the obtained product into a compound II in the presence of carbonyl reduction enzyme; taking the compound II, enabling the compound II to carry out cyclization reaction with benzylamine in a solvent in the presence of cesium carbonate, enabling the obtained product to be reacted with DPPA and preparing a compound IV; reducing nitrine group of the compound IV to prepare a compound V; connecting primary amine group of the compound V with a BOC protection group to obtain a compound VI; reducing the compound VI through Pd/C, enabling theobtained product to be reacted with 8-chlorine-6,7-difluoro-1-[(1R,2s)-2-fluorocyclopropyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester to prepare a compound VIII; and carrying out deprotection of the compound VIII to obtain sitafloxacin hydrate. The sitafloxacin hydrate is few in preparation steps, simple in post-treatment and relatively high in yield.
A Sitafloxacine intermediate, Sitafloxacine preparation method and Sitafloxacine pharmaceutical composition
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, (2017/01/19)
The invention discloses a sitafloxacin intermediate, a preparation method of sitafloxacin and a sitafloxacin pharmaceutical composition. The preparation method can be used for solving the problems of low yield, troublesome aftertreatment, poor safety and higher cost in the existing sitafloxacin preparation. The preparation method disclosed by the invention is simple in process, easily available in raw materials, lower in cost, the solvent after reaction is easy to treat, high yield and quite suitable for large-scale industrial production. The sitafloxacin pharmaceutical composition obtained by virtue of the preparation method provided by the invention can be used for further improving the product dissolution effect, improving the in-vivo bioavailability of the sitafloxacin and enhancing the exertion of medical effect.
Synthesis and characterization of sitafloxacin
Liu, Yu,Liu, Lianxin,Shi, Guangxia
, p. 7049 - 7051 (2015/02/19)
The convenient protocol for the synthesis of sitafloxacin is described. Reaction of ethyl 3-(3-choloro-2,4,5-trifluorophenyl)-3-oxopropanoate with triethylorthoformate and (1R,2S)-(-)-cis-1,2 fluorine cyclopropane amino-p-toluene sulfonic acid salt by condensation under sodium hydrogen condition. The reaction mixture take place hydrolysis of ester in hydrochloric acid solution. Subsequence reacted with (S)-N[(oxoboryl) methylene] -5-azaspiro[2,4]heptan-7-amine by condensation. In the end taken off the protection group gives sitafloxacin and total conversion about 52-65%. The structure of sitafloxacin was characterized by 1H NMR, 13C NMR, IR, MS and elemental analysis.