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Merck
CN

SML2744

Sitafloxacin sesquihydrate

≥98% (HPLC)

Synonym(s):

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), DU 6859 sesquihydrate, DU 6859a sesquihydrate, DU-6859 sesquihydrate, DU-6859a sesquihydrate, DU6859 sesquihydrate, DU6859a sesquihydrate

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About This Item

Empirical Formula (Hill Notation):
C19H18ClF2N3O3·1.5H2O
CAS Number:
163253-35-8
Molecular Weight:
436.84
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00903720

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SMILES string

F[C@@H]1[C@@H](C1)N2c3c(cc(c(c3Cl)N4C[C@H](C5(C4)CC5)N)F)C(=O)C(=C2)C(=O)O.O

InChI

1S/C19H18ClF2N3O3.H2O/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);1H2/t10-,12+,13+;/m0./s1

InChI key

ANCJYRJLOUSQBW-JJZGMWGRSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Orally active, 4th generation fluoroquinolone broad-spectrum antibiotic with dual DNA gyrase and topoisomerase IV inhibitory activity.
Sitafloxacin (DU-6859 or DU-6859a) is an orally active, fourth generation fluoroquinolone that exhibits broad-spectrum antibiotic activity against many Gram-positive, Gram-negative and anaerobic clinical isolates, including strains resistant to other fluoroquinolones, via dual inhibitory activity against bacterial DNA gyrase and topoisomerase IV (IC50 = 1.16 and 1.88 μg/mL against S. pneumoniae gyrA/B and parC/E, respectively). Sitafloxacin is active against methicillin-resistant staphylococci, Streptococcus pneumoniae and other streptococci with reduced susceptibility to levofloxacin and other quinolones and enterococci. Sitafloxacin also exhibits activity against clinical isolates of Klebsiella pneumoniae, Enterobacter cloacae, Pseudomonas aeruginosa as well as some activity against quinolone-resistant strains and Acinetobacter baumannii. Sitafloxacin in vitro activity against anaerobes is comparable to imipenem and metronidazole.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000478363
0000478363
0000094087
0000094086
0000083964

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Lina Yi et al.
Journal of medical microbiology, 66(6), 770-776 (2017-06-10)
Purpose. Sitafloxacin (SFX) is a new fluoroquinolone (FQ) that has shown a strong bactericidal effect against Mycobacterium tuberculosis (Mtb) in vitro. However, data on SFX efficacy against Mtb with gyrA/B mutations and its epidemiological cut-off (ECOFF) value remain limited. Therefore
T Akasaka et al.
Antimicrobial agents and chemotherapy, 42(5), 1284-1287 (1998-05-21)
The in vitro inhibitory effects of sitafloxacin (DU-6859a) and its three stereoisomers on bacterial DNA gyrase from Escherichia coli, topoisomerase IV from Staphylococcus aureus, and topoisomerase II from human placenta were compared. No correlation was observed between the inhibitory activities
David Leif Anderson
Drugs of today (Barcelona, Spain : 1998), 44(7), 489-501 (2008-09-23)
Sitafloxacin hydrate (DU-6859a, Gracevit), a new-generation, broad-spectrum oral fluoroquinolone that is very active against many Gram-positive, Gram-negative and anaerobic clinical isolates, including strains resistant to other fluoroquinolones, was recently approved in Japan for the treatment of respiratory and urinary tract
J F Tomayko et al.
Diagnostic microbiology and infectious disease, 20(1), 45-47 (1994-09-01)
The activity of DU-6859a, a new fluoroquinolone antimicrobial agent, was compared with that of ciprofloxacin by agar dilution susceptibility testing against enteric pathogens and multiresistant Escherichia coli. The results indicate that DU-6859a inhibits most of these organisms at concentrations similar
Xiaomeng Dong et al.
International journal of clinical and experimental medicine, 8(5), 8135-8140 (2015-07-30)
To detect the in vitro activities of sitafloxacin alone and in combination with rifampin, colistin, sulbactam, and tigecycline against extensively drug-resistant Acinetobacter baumannii (XDR-A. baumannii). 24 XDR-A. baumannii strains were isolated from patients' specimens. Broth microdilution assay was used to
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