Zabofloxacin HCl

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

MedKoo CAT#: 326917

CAS#: 623574-00-5 (HCl)

Description: Zabofloxacin, also known as DW-224; DW-224a; PB-101, is DNA topoisomerase IV inhibitor potentially for the treatment of chronic obstructive pulmonary disease. Zabofloxacin shows activity for multidrug-resistant infections due to Gram-positive bacteria. Zabofloxacin has a broad spectrum of antimicrobial activity, which is especially potent against Gram-positive bacteria.


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Zabofloxacin HCl is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326917
Name: Zabofloxacin HCl
CAS#: 623574-00-5 (HCl)
Chemical Formula: C19H21ClFN5O4
Exact Mass:
Molecular Weight: 437.8564
Elemental Analysis: C, 52.12; H, 4.83; Cl, 8.10; F, 4.34; N, 15.99; O, 14.62


Related CAS #: 219680-11-2(free base)   623574-00-5(HCl)    

Synonym: DW-224; DW 224; DW224; DW-224a; PB-101; Zabofloxacin

IUPAC/Chemical Name: (E)-1-cyclopropyl-6-fluoro-7-(8-(methoxyimino)-2,6-diazaspiro[3.4]octan-6-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid hydrochloride

InChi Key: IFPBSRFVNPCZMK-BJMORVNCSA-N

InChi Code: InChI=1S/C19H20FN5O4.ClH/c1-29-23-14-6-24(9-19(14)7-21-8-19)17-13(20)4-11-15(26)12(18(27)28)5-25(10-2-3-10)16(11)22-17;/h4-5,10,21H,2-3,6-9H2,1H3,(H,27,28);1H/b23-14-;

SMILES Code: O=C(C1=CN(C2CC2)C3=NC(N(C/C4=N/OC)CC54CNC5)=C(F)C=C3C1=O)O.[H]Cl


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#
219680-11-2(Zabofloxacin )
623574-00-5(Zabofloxacin Hydrochloride)


References

1: Kim T, Park SJ, Chong YP, Park KH, Lee YM, Hong HL, Kim HS, Kim ES, Lee S, Choi DR, Kim SH, Jeong JY, Lee SO, Choi SH, Woo JH, Kim YS. Fluoroquinolone resistance of Streptococcus pneumoniae isolates causing invasive disease: special focus on zabofloxacin. Diagn Microbiol Infect Dis. 2016 Jul 22. pii: S0732-8893(16)30227-9. doi: 10.1016/j.diagmicrobio.2016.07.019. [Epub ahead of print] PubMed PMID: 27498611.

2: Kocsis B, Domokos J, Szabo D. Chemical structure and pharmacokinetics of novel quinolone agents represented by avarofloxacin, delafloxacin, finafloxacin, zabofloxacin and nemonoxacin. Ann Clin Microbiol Antimicrob. 2016 May 23;15(1):34. doi: 10.1186/s12941-016-0150-4. Review. PubMed PMID: 27215369; PubMed Central PMCID: PMC4878067.

3: Rhee CK, Chang JH, Choi EG, Kim HK, Kwon YS, Kyung SY, Lee JH, Park MJ, Yoo KH, Oh YM. Zabofloxacin versus moxifloxacin in patients with COPD exacerbation: a multicenter, double-blind, double-dummy, randomized, controlled, Phase III, non-inferiority trial. Int J Chron Obstruct Pulmon Dis. 2015 Oct 22;10:2265-75. doi: 10.2147/COPD.S90948. eCollection 2015. PubMed PMID: 26543359; PubMed Central PMCID: PMC4622522.

4: Van Bambeke F. Renaissance of antibiotics against difficult infections: Focus on oritavancin and new ketolides and quinolones. Ann Med. 2014 Nov;46(7):512-29. doi: 10.3109/07853890.2014.935470. Epub 2014 Jul 24. Review. PubMed PMID: 25058176.

5: Karpiuk I, Tyski S. Looking for the new preparations for antibacterial therapy III. New antimicrobial agents from the quinolones group in clinical trials. Przegl Epidemiol. 2013;67(3):455-60, 557-61. English, Polish. PubMed PMID: 24340560.

6: Han H, Kim SE, Shin KH, Lim C, Lim KS, Yu KS, Cho JY. Comparison of pharmacokinetics between new quinolone antibiotics: the zabofloxacin hydrochloride capsule and the zabofloxacin aspartate tablet. Curr Med Res Opin. 2013 Oct;29(10):1349-55. doi: 10.1185/03007995.2013.825591. Epub 2013 Aug 19. PubMed PMID: 23865727.

7: Jin HE, Kang IH, Shim CK. Fluorescence detection of Zabofloxacin, a novel fluoroquinolone antibiotic, in plasma, bile, and urine by HPLC: the first oral and intravenous applications in a pharmacokinetic study in rats. J Pharm Pharm Sci. 2011;14(3):291-305. PubMed PMID: 21824450.

8: Jin HE, Lee KR, Kang IH, Chung SJ, Shim CK. Determination of zabofloxacin in rat plasma by liquid chromatography with mass spectrometry and its application to pharmacokinetic study. J Pharm Biomed Anal. 2011 Mar 25;54(4):873-7. doi: 10.1016/j.jpba.2010.11.001. Epub 2010 Nov 9. PubMed PMID: 21112170.

9: Park HS, Jung SJ, Kwak JH, Choi DR, Choi EC. DNA gyrase and topoisomerase IV are dual targets of zabofloxacin in Streptococcus pneumoniae. Int J Antimicrob Agents. 2010 Jul;36(1):97-8. doi: 10.1016/j.ijantimicag.2010.02.022. Epub 2010 Apr 18. PubMed PMID: 20403681.

10: Jones RN, Biedenbach DJ, Ambrose PG, Wikler MA. Zabofloxacin (DW-224a) activity against Neisseria gonorrhoeae including quinolone-resistant strains. Diagn Microbiol Infect Dis. 2008 Sep;62(1):110-2. doi: 10.1016/j.diagmicrobio.2008.05.010. Epub 2008 Jul 11. PubMed PMID: 18620833.

11: Kwon AR, Min YH, Ryu JM, Choi DR, Shim MJ, Choi EC. In vitro and in vivo activities of DW-224a, a novel fluoroquinolone antibiotic agent. J Antimicrob Chemother. 2006 Sep;58(3):684-8. Epub 2006 Jul 27. PubMed PMID: 16873394.

12: Park HS, Kim HJ, Seol MJ, Choi DR, Choi EC, Kwak JH. In vitro and in vivo antibacterial activities of DW-224a, a new fluoronaphthyridone. Antimicrob Agents Chemother. 2006 Jun;50(6):2261-4. PubMed PMID: 16723601; PubMed Central PMCID: PMC1479124.

13: Kosowska-Shick K, Credito K, Pankuch GA, Lin G, Bozdogan B, McGhee P, Dewasse B, Choi DR, Ryu JM, Appelbaum PC. Antipneumococcal activity of DW-224a, a new quinolone, compared to those of eight other agents. Antimicrob Agents Chemother. 2006 Jun;50(6):2064-71. PubMed PMID: 16723567; PubMed Central PMCID: PMC1479131.

14: Kim HJ, Seol MJ, Park HS, Choi DR, Seong SK, Shin HK, Kwak JH. Antimicrobial activity of DW-224a, a new fluoroquinolone, against Streptococcus pneumoniae. J Antimicrob Chemother. 2006 Jun;57(6):1256-8. Epub 2006 Apr 7. PubMed PMID: 16603643.

15: Kim EJ, Shin WH, Kim KS, Han SS. Safety pharmacology of DW-224a, a novel fluoroquinolone antibiotic agent. Drug Chem Toxicol. 2004 Nov;27(4):295-307. PubMed PMID: 15573468.

16: Han J, Kim JC, Chung MK, Kim B, Choi DR. Subacute toxicity and toxicokinetics of a new antibiotic, DW-224a, after single and 4-week repeated oral administration in dogs. Biol Pharm Bull. 2003 Jun;26(6):832-9. PubMed PMID: 12808295.