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Sitafloxacin

Fluoroquinolone antibiotic CAS# 127254-12-0

Sitafloxacin

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Chemical structure

Sitafloxacin

3D structure

Chemical Properties of Sitafloxacin

Cas No. 127254-12-0 SDF Download SDF
PubChem ID 73011 Appearance Powder
Formula C19H18ClF2N3O3 M.Wt 409.81
Type of Compound N/A Storage Desiccate at -20°C
Synonyms DU6859a
Solubility Soluble in DMSO
Chemical Name 7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(2S)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid
SMILES C1CC12CN(CC2N)C3=C(C=C4C(=C3Cl)N(C=C(C4=O)C(=O)O)C5CC5F)F
Standard InChIKey PNUZDKCDAWUEGK-RDWQBYKPSA-N
Standard InChI InChI=1S/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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Sitafloxacin

DescriptionSitafloxacin is a new-generation, broad-spectrum oral fluoroquinolone antibiotic. Target: Antibacterial Sitafloxacin, 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 infections [1]. In terms of clinical efficacy, oral sitafloxacin was noninferior to oral levofloxacin in the treatment of community-acquired pneumonia or an infectious exacerbation of chronic respiratory tract disease, noninferior to oral tosufloxacin in the treatment of community-acquired pneumonia, and noninferior to oral levofloxacin in the treatment of complicated urinary tract infections, according to the results of randomized, double-blind, multicentre, noninferiority trials. Noncomparative studies demonstrated the efficacy of oral sitafloxacin in otorhinolaryngological infections, urethritis in men, C. trachomatis-associated cervicitis in women and odontogenic infections [2].

References:
[1]. Anderson, D.L., Sitafloxacin hydrate for bacterial infections. Drugs Today (Barc), 2008. 44(7): p. 489-501. [2]. Keating, G.M., Sitafloxacin: in bacterial infections. Drugs, 2011. 71(6): p. 731-44.

Sitafloxacin Dilution Calculator

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Sitafloxacin Molarity Calculator

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Preparing Stock Solutions of Sitafloxacin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4402 mL 12.2008 mL 24.4016 mL 48.8031 mL 61.0039 mL
5 mM 0.488 mL 2.4402 mL 4.8803 mL 9.7606 mL 12.2008 mL
10 mM 0.244 mL 1.2201 mL 2.4402 mL 4.8803 mL 6.1004 mL
50 mM 0.0488 mL 0.244 mL 0.488 mL 0.9761 mL 1.2201 mL
100 mM 0.0244 mL 0.122 mL 0.244 mL 0.488 mL 0.61 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Sitafloxacin

Sitafloxacin is anantibiotic against gram-positive, gram-negativeand anaerobebacteria[1].

Sitafloxacin is a novel fluoroquinolone antibiotic with a broad antibacterial spectrum. It has activity against Enterobacterial species (gram-positive bacteria) with MIC50 values ranging from 0.008 to 1mg/ml and MIC90 values ranging from 0.015 to 2mg/ml. For the gram-negative bacteria, sitafloxacinis are found to be above eight-fold effective than ciprofloxacin against Acinetobacter spp. with MIC values ranging from 0.008 to 8mg/ml. Besides, sitafloxacinis are reported to inhibit anaerobic bacteria including Bacteroides species, Clostridium perfringens and Peptostreptococcus spp. with the MIC50 values ranging from 0.03 to 0.12mg/ml and MIC90 values ranging from 0.06 to 0.25 mg/ml [1].

References:
[1] Milatovic D1, Schmitz FJ, Brisse S, Verhoef J, Fluit AC. In vitro activities of sitafloxacin (DU-6859a) and six other fluoroquinolones against 8,796 clinical bacterial isolates.Antimicrob Agents Chemother. 2000 Apr;44(4):1102-7.

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References on Sitafloxacin

Four-times-daily Dosing of Rabeprazole with Sitafloxacin, High-Dose Amoxicillin, or Both for Metronidazole-Resistant Infection with Helicobacter pylori in Japan.[Pubmed:27213463]

Helicobacter. 2017 Feb;22(1).

BACKGROUND: The bacterial resistance of Helicobacter pylori to antimicrobial agents such as clarithromycin and metronidazole has been increasing worldwide, leading to the failure of eradication treatment. Here, we present an eradication regimen consisting of four-times-daily dosing (q.i.d.) of rabeprazole with potent acid inhibition. AIM: To investigate the efficacy of eradication therapy with rabeprazole q.i.d. and amoxicillin or Sitafloxacin in Japanese infected with a metronidazole-resistant strain. METHODS: We retrospectively investigated the efficacy of eradication regimens with rabeprazole q.i.d. for 7 days in 111 Japanese pooled patients infected with a metronidazole-resistant strain of H. pylori at Hamamatsu University School of Medicine Hospital or the Shiga University of Medical Science Hospital: 1, with Sitafloxacin 100 mg twice daily (b.i.d.) (n = 82); 2, with amoxicillin 500 mg q.i.d. (n = 15); and 3, with amoxicillin q.i.d. and Sitafloxacin b.i.d.-combined regimen (n = 14). Eradication status was assessed at 8 weeks via a (13) C-urea breath test. RESULTS: Eradication rate on intention-to-treat analysis was 93.7% (95% confidence interval: 87.4-97.4%, 104/111), irrespective of the high prevalence of strains resistant to clarithromycin (81.1%, 90/111) and levofloxacin (42.3%, 47/111). No significant differences in eradication rates were observed among the different treatment regimens (p = .408), eradication history (p = .096) and different CYP2C19 genotypes (p = .789). On multivariate analysis, no significant risk factor for eradication failure by therapy with potent acid inhibition was seen. CONCLUSION: In Japanese patients infected with metronidazole-resistant strains of H. pylori, eradication rates exceeding 90% can be achieved using appropriate dosing of antibiotic agents with strain susceptibility (amoxicillin q.i.d. and/or Sitafloxacin b.i.d.) together with acid inhibition for a full 24 h and rabeprazole 10 mg q.i.d. These findings may be further evidence for dual therapy with rabeprazole q.i.d. and an antibiotic agent (amoxicillin q.i.d. or Sitafloxacin b.i.d.) in Japanese patients with metronidazole-resistant strains.

Clinical pharmacokinetics of oral levofloxacin and sitafloxacin in epididymal tissue.[Pubmed:28089362]

J Infect Chemother. 2017 Apr;23(4):214-217.

OBJECTIVES: This study aimed to investigate the penetration of fluoroquinolones into human epididymal tissue. METHODS: The penetration of levofloxacin (LVFX) 500 mg or Sitafloxacin (STFX) 100 mg into epididymal tissue was examined. Patients with prostate cancer who were referred for orchiectomy were included. LVFX 500 mg (n = 9) or STFX 100 mg (n = 9) was administered orally 1 h before orchiectomy, and 0.5 g of epididymal tissue and blood samples were collected simultaneously during surgery. Drug concentrations were measured by high-performance liquid chromatography, and patient characteristics and adverse events were analyzed. RESULTS: The mean ratio of the epididymal concentration to the serum concentration was 1.48 +/- 0.45 for LVFX and 1.54 +/- 0.81 for STFX. For LVFX, the simulated curves estimated the following: maximum concentrations (Cmax) of 8.84 mug/ml in serum and 14.1 mug/g in epididymal tissue and area under the concentration-time curve for 24 h (AUC24) of 68.5 mug h/ml in serum and 108.9 mug h/g in epididymal tissue. For STFX, the Cmax was 1.22 mug/ml in serum and 1.66 mug/g in epididymal tissue, and the AUC24 was 9.58 mug h/ml in serum and 13.1 mug h/g in epididymal tissue. Neither treatment-related adverse events nor postoperative urogenital infections were observed. CONCLUSIONS: The results of this study suggest that oral administration of LVFX 500 mg or STFX 100 mg achieves effective epididymal concentrations for treatment of epididymitis.

Efficacy of triple therapy with esomeprazole, amoxicillin, and sitafloxacin as a third-line Helicobacter pylori eradication regimen.[Pubmed:27590563]

Int J Infect Dis. 2016 Oct;51:66-69.

OBJECTIVE: To examine the efficacy of third-line Helicobacter pylori eradication therapy with esomeprazole, amoxicillin, and Sitafloxacin for patients with clarithromycin- and metronidazole-based first- and second-line therapy failure. METHODS: Thirty patients with first- and second-line H. pylori eradication failure were treated prospectively with esomeprazole 20mg twice daily, amoxicillin 750mg twice daily, and Sitafloxacin 100mg twice daily for 7 days. After 8-12 weeks, the outcome of eradication therapy was assessed by (13)C-urea breath test or stool antigen test. RESULTS: All 30 patients completed the study. Eradication was successful in 25 patients and the eradication rate was 83% in the intention-to-treat and per-protocol analyses. No specific or significant adverse events were recorded in the 30 patients. Patient characteristics such as sex, body mass index, and pepsinogen I/II ratio did not differ between patients who were treated successfully and those who were not treated successfully. CONCLUSIONS: Third-line H. pylori eradication therapy with esomeprazole, amoxicillin, and Sitafloxacin is as safe and effective as previously reported Sitafloxacin-based triple therapy.

Preliminary Evaluation of a Sitafloxacin-Containing Regimen for Relapsed or Refractory Pulmonary Mycobacterium avium Complex Disease.[Pubmed:27704005]

Open Forum Infect Dis. 2016 Jul 13;3(3):ofw147.

Although Sitafloxacin (STFX) is known to have a favorable minimum inhibitory concentration for Mycobacterium avium, few studies have evaluated the clinical efficacy of an STFX-containing regimen for pulmonary M avium complex (MAC) disease. To evaluate the clinical efficacy of STFX-containing regimens for relapsed or refractory pulmonary MAC disease, we retrospectively reviewed 18 patients with pulmonary MAC disease who received STFX for at least 4 weeks for pulmonary MAC disease between January 2008 and February 2016. Of 18 patients, 10 (55.6%) showed improved radiological characteristics and 8 (44.4%) showed negative sputum cultures at 6 months. Regarding the clinical symptoms, improvements were observed in decreasing order in sputum production (77.8%), cough (72.2%), and malaise (55.6%). Common adverse events included nausea or vomiting (38.9%), followed by loose stool or diarrhea (27.8%) and sleepiness (11.1%). Although this study contained a small number of subjects, we describe a STFX-containing regimen that was effective in achieving sputum culture negative conversions and had an acceptable adverse events profile.

Description

Sitafloxacin is a new-generation, broad-spectrum oral fluoroquinolone antibiotic.

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