Sitafloxacin anhydrous
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MedKoo CAT#: 326821

CAS#: 127254-12-0 (anhydrous)

Description: Sitafloxacin is 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. Sitafloxacin is active against methicillin-resistant staphylococci, Streptococcus pneumoniae and other streptococci with reduced susceptibility to levofloxacin and other quinolones and enterococci.


Price and Availability

Size
Price

10mg
USD 90
100mg
USD 450
1g
USD 1250
10g
USD 5950
Size
Price

25mg
USD 150
200mg
USD 650
2g
USD 2150
20g
Not available
Size
Price

50mg
USD 250
500mg
USD 950
5g
USD 3950
50g
Ask price

Sitafloxacin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326821
Name: Sitafloxacin anhydrous
CAS#: 127254-12-0 (anhydrous)
Chemical Formula: C19H18ClF2N3O3
Exact Mass: 409.1005
Molecular Weight: 409.8178
Elemental Analysis: C, 55.69; H, 4.43; Cl, 8.65; F, 9.27; N, 10.25; O, 11.71


Synonym: DU 6859; DU-6859; DU6859; DU 6859A; DU-6859A; DU6859A; Sitafloxacin; Sitafloxacin hydrate, Sitafloxacin anhydrous, Trade name: Gracevit.

IUPAC/Chemical Name: 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

SMILES Code: O=C(C1=CN([C@H]2[C@@H](F)C2)C3=C(C=C(F)C(N(C[C@H]4N)CC54CC5)=C3Cl)C1=O)O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Related CAS#
CAS#127254-12-0 (Sitafloxacin anhydrous)
CAS#(163253-35-8 (Sitafloxacin sesquihydrate)
CAS#163253-37-0 (Sitafloxacin monohydrate)

Sitafloxacin has also demonstrated activity against clinical isolates of Klebsiella pneumoniae (including about 67% of strains producing extended-spectrum, beta-lactamases and resistant to ciprofloxacin), Enterobacter cloacae, Pseudomonas aeruginosa with some activity against quinolone-resistant strains and Acinetobacter baumannii. The in vitro activity against anaerobes is comparable to imipenem or metronidazole. In a published phase II randomized, open-label, multicenter study of patients hospitalized with pneumonia, sitafloxacin (400 mg once daily) was comparable to imipenem/cilastatin (500 mg three times a day). Results of the phase III trials of sitafloxacin are not available in English. The clinical safety profile of sitafloxacin has been characterized from 1,059 patients who participated in 10 clinical trials. The most common events with 50 or 100 mg twice daily were gastrointestinal disorders (17.2%), mostly diarrhea, and abnormal laboratory test results (16.2%), mostly liver enzyme elevations. For Japanese patients, sitafloxacin provides the broad-spectrum coverage promised by clinafloxacin and trovafloxacin and comparable to carbapenems. While it is currently limited by its potential for phototoxicity in Caucasians, phototoxicity is essentially irrelevant if sitafloxacin is used in hospitals and especially in intensive care units.


References

1: Sugimoto M, Sahara S, Ichikawa H, Kagami T, Ban H, Otsuka T, Andoh A, Furuta T. Four-times-daily Dosing of Rabeprazole with Sitafloxacin, High-Dose Amoxicillin, or Both for Metronidazole-Resistant Infection with Helicobacter pylori in Japan. Helicobacter. 2016 May 23. doi: 10.1111/hel.12319. [Epub ahead of print] PubMed PMID: 27213463.

2: Manosuthi W, Wiboonchutikul S. Treatment outcomes of oral sitafloxacin in acute complicated urinary tract infection and pyelonephritis. Springerplus. 2016 Apr 5;5:410. doi: 10.1186/s40064-016-2044-5. eCollection 2016. PubMed PMID: 27069830; PubMed Central PMCID: PMC4821846.

3: Nakajima T, Okui T, Ito H, Nakajima M, Honda T, Shimada Y, Tabeta K, Akazawa K, Yamazaki K. Microbiological and Clinical Effects of Sitafloxacin and Azithromycin in Periodontitis Patients Receiving Supportive Periodontal Therapy. Antimicrob Agents Chemother. 2016 Jan 4;60(3):1779-87. doi: 10.1128/AAC.02575-15. PubMed PMID: 26729495; PubMed Central PMCID: PMC4775917.

4: Mori H, Suzuki H, Matsuzaki J, Tsugawa H, Fukuhara S, Miyoshi S, Hirata K, Seino T, Matsushita M, Masaoka T, Kanai T. Efficacy of 10-day Sitafloxacin-Containing Third-Line Rescue Therapies for Helicobacter pylori Strains Containing the gyrA Mutation. Helicobacter. 2016 Aug;21(4):286-94. doi: 10.1111/hel.12286. Epub 2015 Nov 27. PubMed PMID: 26612407.

5: Sugimoto M. Letter: sitafloxacin for H. pylori infection in Japan: considerations on resistance rates, generalisability and its place in the therapeutic algorithm - author's reply. Aliment Pharmacol Ther. 2015 Oct;42(7):943-4. doi: 10.1111/apt.13359. PubMed PMID: 26331564.

6: Molina-Infante J, Gisbert JP. Letter: sitafloxacin for H. pylori infection in Japan: considerations on resistance rates, generalisability and its place in the therapeutic algorithm. Aliment Pharmacol Ther. 2015 Oct;42(7):942-3. doi: 10.1111/apt.13350. PubMed PMID: 26331563.

7: Dong X, Chen F, Zhang Y, Liu H, Liu Y, Ma L. In vitro activities of sitafloxacin tested alone and in combination with rifampin, colistin, sulbactam, and tigecycline against extensively drug-resistant Acinetobacter baumannii. Int J Clin Exp Med. 2015 May 15;8(5):8135-40. eCollection 2015. PubMed PMID: 26221381; PubMed Central PMCID: PMC4509326.

8: Sugimoto M, Sahara S, Ichikawa H, Kagami T, Uotani T, Furuta T. High Helicobacter pylori cure rate with sitafloxacin-based triple therapy. Aliment Pharmacol Ther. 2015 Aug;42(4):477-83. doi: 10.1111/apt.13280. Epub 2015 Jun 15. PubMed PMID: 26075959.

9: Fujita M, Matsumoto T, Hirano R, Harada E, Ikegame S, Nakanishi Y, Watanabe K. [Measurement of sitafloxacin MIC for Mycobacterium avium complex and application for treatment of pulmonary nontuberculous mycobacteriosis]. Jpn J Antibiot. 2014 Dec;67(6):395-400. Japanese. PubMed PMID: 25796743.

10: Tomita S, Kasai S, Imamura K, Ihara Y, Kita D, Ota K, Sekino J, Nakagawa T, Saito A. Changes in antimicrobial susceptibility profile and prevalence of quinolone low-sensitive strains in subgingival plaque from acute periodontal lesions after systemic administration of sitafloxacin. Microb Pathog. 2015 Feb;79:41-6. doi: 10.1016/j.micpath.2015.01.005. Epub 2015 Jan 17. PubMed PMID: 25602787.

11: Ikeda T, Kuraguchi J, Kogashiwa Y, Yokoi H, Satomi T, Kohno N. Successful treatment of bisphosphonate-related osteonecrosis of the jaw (BRONJ) patients with sitafloxacin: new strategies for the treatment of BRONJ. Bone. 2015 Apr;73:217-22. doi: 10.1016/j.bone.2014.12.021. Epub 2014 Dec 27. PubMed PMID: 25549869.

12: Wu G, Wu L, Hu X, Zhou H, Liu J, Zhu M, Zheng Y, Zhai Y, Shentu J. Pharmacokinetics and safety of sitafloxacin after single oral doses in healthy volunteers. Int J Clin Pharmacol Ther. 2014 Dec;52(12):1037-44. doi: 10.5414/CP202147. PubMed PMID: 25250613.

13: Deguchi T, Kikuchi M, Yasuda M, Ito S. Sitafloxacin: antimicrobial activity against ciprofloxacin-selected laboratory mutants of Mycoplasma genitalium and inhibitory activity against its DNA gyrase and topoisomerase IV. J Infect Chemother. 2015 Jan;21(1):74-5. doi: 10.1016/j.jiac.2014.08.021. Epub 2014 Sep 22. PubMed PMID: 25245990.

14: Hori S, Uchino K, Matsumoto T, Yamaguchi H, Takahashi M, Hamajima S, Nukui K, Eda H, Shiina A, Takita A, Yamanouchi N, Mizuno M, Okutani Y. [Study on the safety and efficacy of sitafloxacin at a dose of 100 mg once a day--results of the use-results survey]. Jpn J Antibiot. 2014 Jun;67(3):175-91. Japanese. PubMed PMID: 25163251.

15: Wang Y, Liu Y, Zhang H, Wang Y, Liu Y, Wang L, Ou N. A simple LC-MS/MS method for determination of sitafloxacin in human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Sep 15;967:219-24. doi: 10.1016/j.jchromb.2014.07.015. Epub 2014 Aug 1. PubMed PMID: 25128880.

16: Thamlikitkul V, Tiengrim S. In vitro susceptibility test of sitafloxacin against resistant gram-negative bacilli isolated from Thai patients by disk diffusion method. J Med Assoc Thai. 2014 Mar;97 Suppl 3:S7-12. PubMed PMID: 24772575.

17: Tomita S, Kasai S, Ihara Y, Imamura K, Kita D, Ota K, Kinumatsu T, Nakagawa T, Saito A. Effects of systemic administration of sitafloxacin on subgingival microflora and antimicrobial susceptibility profile in acute periodontal lesions. Microb Pathog. 2014 Jun-Jul;71-72:1-7. doi: 10.1016/j.micpath.2014.04.003. Epub 2014 Apr 18. PubMed PMID: 24747615.

18: Huang YS, Wang JT, Sheng WH, Chuang YC, Chang SC. Comparative in vitro activity of sitafloxacin against bacteremic isolates of carbapenem resistant Acinetobacter baumannii complex. J Microbiol Immunol Infect. 2015 Oct;48(5):545-51. doi: 10.1016/j.jmii.2014.02.002. Epub 2014 Mar 21. PubMed PMID: 24662017.

19: Huang K, Yang J, Zhang J, Ding Y, Chen L, Xu WY, Xu XJ, Duan R, He Q. Determination of sitafloxacin in human plasma by liquid chromatography-tandem mass spectrometry method: application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Apr 15;957:36-40. doi: 10.1016/j.jchromb.2014.03.004. Epub 2014 Mar 12. PubMed PMID: 24657409.

20: Amano A, Matsuzaki K, Kishi N, Koyama H, Hasegawa M, Ikeda F, Matsumoto T, Yamaguchi H, Okutani Y. [In vitro activity of sitafloxacin against clinical isolates in 2012]. Jpn J Antibiot. 2013 Dec;66(6):311-30. Japanese. PubMed PMID: 24649797.