Sitafloxacin | CAS#163253-35-8 | antiboitics

MedKoo Cat#: 326821 | Name: Sitafloxacin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Sitafloxacin

CAS#163253-35-8 (1.5 hydrate)

Theoretical Analysis

MedKoo Cat#: 326821

Name: Sitafloxacin

CAS#: 163253-35-8 (1.5 hydrate)

Chemical Formula: C38H42Cl2F4N6O9

Exact Mass: 409.1005

Molecular Weight: 873.68

Elemental Analysis: C, 52.24; H, 4.85; Cl, 8.12; F, 8.70; N, 9.62; O, 16.48

Price and Availability

Size	Price	Availability
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 650.00	Ready to ship
500mg	USD 950.00	Ready to ship
1g	USD 1,650.00	Ready to ship
2g	USD 2,950.00	Ready to ship
5g	USD 4,950.00	Ready to ship
10g	USD 7,650.00	Ready to ship

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Related CAS #

163253-35-8 (1.5 hydrate) 127254-12-0 (anhydrous) 163253-37-0 (hydrate)

Synonym

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

IUPAC/Chemical Name

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)

InChi Key

MPORYQCGWFQFLA-ONPDANIMSA-N

InChi Code

InChI=1S/2C19H18ClF2N3O3.3H2O/c2*20-14-15-8(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;;;/h2*3,5,10,12-13H,1-2,4,6-7,23H2,(H,27,28);3*1H2/t2*10-,12+,13+;;;/m00.../s1

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.O=C(C6=CN([C@H]7[C@@H](F)C7)C8=C(C=C(F)C(N(C[C@H]9N)CC%109CC%10)=C8Cl)C6=O)O.[H]O[H].[H]O[H].[H]O[H]

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 and water

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).

HS Tariff Code

2934.99.9001

More Info

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.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# C20R01B02

QC Data

View QC data: current batch, Lot# C20R01B02

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Sitafloxacin shows antichlamydial activity and antibacterial activities against a broad range of gram-positive and gram-negative bacteria (including anaerobic bacteria) as well as against atypical pathogens.

In vitro activity:

Sitafloxacin can be an effective treatment for sepsis. The percentage of intracellular TNFα increased in LPS-stimulated cells with sitafloxacin compared with that in LPS-stimulated cells. One of the mechanisms underlying inhibition of TNFα production in LPS-stimulated THP-1 cells treated with sitafloxacin is the inhibition of TNFα release from cells via the suppression of TACE phosphorylation and activity. Reference: Sci Rep. 2021 Dec 17;11(1):24154. https://pubmed.ncbi.nlm.nih.gov/34921186/

In vivo activity:

Sitafloxacin displays good potency against H. influenzaepneumonia. Sitafloxacin completely eradicated viable bacteria from all mouse lungs. Histopathological studies of lung tissue from control mice showed the presence of progressive pneumonia, whereas in sitafloxacin treated mice, total cell counts and neutrophil counts in BALF decreased. Additionally, only a small number of neutrophils were seen in alveolar walls, and inflammatory changes were apparently improved. Reference: Int J Antimicrob Agents. 2009 Sep;34(3):210-4. https://pubmed.ncbi.nlm.nih.gov/19394203/

	Solvent	mg/mL	mM
Solubility
	DMSO	6.5	7.38
	Water	1.0	1.14

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 873.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Leechawengwongs M, Prammananan T, Jaitrong S, Billamas P, Makhao N, Thamnongdee N, Thanormchat A, Phurattanakornkul A, Rattanarangsee S, Ratanajaraya C, Disratthakit A, Chaiprasert A. In Vitro Activity and MIC of Sitafloxacin against Multidrug-Resistant and Extensively Drug-Resistant Mycobacterium tuberculosis Isolated in Thailand. Antimicrob Agents Chemother. 2017 Dec 21;62(1):e00825-17. doi: 10.1128/AAC.00825-17. PMID: 29061759; PMCID: PMC5740303. 2. 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. PMID: 26221381; PMCID: PMC4509326. 3. Sakamaki I, Fukushi M, Ohashi W, Tanaka Y, Itoh K, Tomihara K, Yamamoto Y, Iwasaki H. Sitafloxacin reduces tumor necrosis factor alpha (TNFα) converting enzyme (TACE) phosphorylation and activity to inhibit TNFα release from lipopolysaccharide-stimulated THP-1 cells. Sci Rep. 2021 Dec 17;11(1):24154. doi: 10.1038/s41598-021-03511-5. PMID: 34921186; PMCID: PMC8683466. 4. Choi YI, Lee SM, Chung JW, Kim KO, Kwon KA, Kim YJ, Kim JH, Lee SM, Jeong JY, Park DK. Therapeutic Potential of Sitafloxacin as a New Drug Candidate for Helicobacter Eradication in Korea: An In Vitro Culture-Based Study. Antibiotics (Basel). 2021 Oct 13;10(10):1242. doi: 10.3390/antibiotics10101242. PMID: 34680822; PMCID: PMC8532961.

In vitro protocol:

In vivo protocol:

1. Sakamaki I, Fukushi M, Ohashi W, Tanaka Y, Itoh K, Tomihara K, Yamamoto Y, Iwasaki H. Sitafloxacin reduces tumor necrosis factor alpha (TNFα) converting enzyme (TACE) phosphorylation and activity to inhibit TNFα release from lipopolysaccharide-stimulated THP-1 cells. Sci Rep. 2021 Dec 17;11(1):24154. doi: 10.1038/s41598-021-03511-5. PMID: 34921186; PMCID: PMC8683466. 2. Choi YI, Lee SM, Chung JW, Kim KO, Kwon KA, Kim YJ, Kim JH, Lee SM, Jeong JY, Park DK. Therapeutic Potential of Sitafloxacin as a New Drug Candidate for Helicobacter Eradication in Korea: An In Vitro Culture-Based Study. Antibiotics (Basel). 2021 Oct 13;10(10):1242. doi: 10.3390/antibiotics10101242. PMID: 34680822; PMCID: PMC8532961.

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.