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| | SITAFLOXACIN Basic information |
| Product Name: | SITAFLOXACIN | | Synonyms: | 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 | | CAS: | 163253-35-8 | | MF: | C19H20ClF2N3O4 | | MW: | 427.83 | | EINECS: | 1308068-626-2 | | Product Categories: | DU 6859A, DU 6859, DU-6859, LS-184401;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors | | Mol File: | 163253-35-8.mol |  |
| | SITAFLOXACIN Chemical Properties |
| 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 | | CAS DataBase Reference | 163253-35-8(CAS DataBase Reference) |
| | SITAFLOXACIN Usage And Synthesis |
| 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 | 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 | | Uses | Antibacterial | | 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. 
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| | SITAFLOXACIN Preparation Products And Raw materials |
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