Gemifloxacin

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

MedKoo CAT#: 598496

CAS#: 175463-14-6

Description: Gemifloxacin is a fluoronaphthyridone.


Price and Availability

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Gemifloxacin 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#: 598496
Name: Gemifloxacin
CAS#: 175463-14-6
Chemical Formula: C18H20FN5O4
Exact Mass: 389.1499
Molecular Weight: 389.38
Elemental Analysis: C, 55.52; H, 5.18; F, 4.88; N, 17.99; O, 16.44


Synonym: Gemifloxacin; SB 265805; SB-265805; SB265805;

IUPAC/Chemical Name: (E)-7-(3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

InChi Key: ZRCVYEYHRGVLOC-HMAPJEAMSA-N

InChi Code: InChI=1S/C18H20FN5O4/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27)/b22-14-

SMILES Code: O=C(C1=CN(C2CC2)C3=NC(N4CC(CN)/C(C4)=N\OC)=C(F)C=C3C1=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:
>3 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:
2934.99.03.00


References

1: Kirkcaldy RD, Weinstock HS, Moore PC, Philip SS, Wiesenfeld HC, Papp JR, Kerndt PR, Johnson S, Ghanem KG, Hook EW 3rd. The efficacy and safety of gentamicin plus azithromycin and gemifloxacin plus azithromycin as treatment of uncomplicated gonorrhea. Clin Infect Dis. 2014 Oct 15;59(8):1083-91. doi: 10.1093/cid/ciu521. Epub 2014 Jul 16. PubMed PMID: 25031289; PubMed Central PMCID: PMC4271098.

2: Kim MJ, Lim HS, Cho SH, Bae KS. Comparative pharmacokinetics and bioavailability of gemifloxacin administered as an intravenous 200 mg formulation or an oral 320 mg tablet. Clin Drug Investig. 2014 Mar;34(3):195-201. doi: 10.1007/s40261-013-0164-z. PubMed PMID: 24385283.

3: Umair M, Javeed A, Ghafoor A, Ashraf M. Immunomodulatory activities of gemifloxacin in mice. Iran J Basic Med Sci. 2016 Sep;19(9):985-992. PubMed PMID: 27803786; PubMed Central PMCID: PMC5080429.

4: Sagirli O, Demirci S, Önal A. A very simple high-performance liquid chromatographic method with fluorescence detection for the determination of gemifloxacin in human breast milk. Luminescence. 2015 Dec;30(8):1326-9. doi: 10.1002/bio.2901. Epub 2015 Mar 25. PubMed PMID: 25808579.

5: Marino A, Blanco AR, Ginestra G, Nostro A, Bisignano G. Ex vivo efficacy of gemifloxacin in experimental keratitis induced by methicillin-resistant Staphylococcus aureus. Int J Antimicrob Agents. 2016 Oct;48(4):395-400. doi: 10.1016/j.ijantimicag.2016.06.026. Epub 2016 Aug 11. PubMed PMID: 27554440.

6: Kim SY, Yim JJ, Park JS, Park SS, Heo EY, Lee CH, Chung HS, Kim DK. Clinical effects of gemifloxacin on the delay of tuberculosis treatment. J Korean Med Sci. 2013 Mar;28(3):378-82. doi: 10.3346/jkms.2013.28.3.378. Epub 2013 Mar 4. PubMed PMID: 23486643; PubMed Central PMCID: PMC3594600.

7: Paim CS, Verlindo de Araújo B, Volpato NM, Steppe M, Schapoval EE. Gemifloxacin mesylate (GFM): dissolution test based on in vivo data. Drug Dev Ind Pharm. 2015 Apr;41(4):567-72. doi: 10.3109/03639045.2014.884128. Epub 2014 Feb 12. PubMed PMID: 24517572.

8: Mahmoudi L, Farshad S, Seddigh M, Mahmoudi P, Ejtehadi F, Niknam R. High efficacy of gemifloxacin-containing therapy in Helicobacter Pylori eradication: A pilot empirical second-line rescue therapy. Medicine (Baltimore). 2016 Oct;95(42):e4410. PubMed PMID: 27759625; PubMed Central PMCID: PMC5079309.

9: Xu Y, Liu Y, Zhao J, Li H, Zhang P, Wang W. Photochemical properties of gemifloxacin: a laser flash photolysis study. J Photochem Photobiol B. 2015 Feb;143:30-7. doi: 10.1016/j.jphotobiol.2014.12.014. Epub 2014 Dec 19. PubMed PMID: 25589341.

10: Dsugi NF, Elbashir AA, Suliman FE. Supramolecular interaction of gemifloxacin and hydroxyl propyl β-cyclodextrin spectroscopic characterization, molecular modeling and analytical application. Spectrochim Acta A Mol Biomol Spectrosc. 2015;151:360-7. doi: 10.1016/j.saa.2015.06.031. Epub 2015 Jun 25. PubMed PMID: 26143328.

11: Blondeau JM, Shebelski SD, Hesje CK. Killing of Streptococcus pneumoniae by azithromycin, clarithromycin, erythromycin, telithromycin and gemifloxacin using drug minimum inhibitory concentrations and mutant prevention concentrations. Int J Antimicrob Agents. 2015 Jun;45(6):594-9. doi: 10.1016/j.ijantimicag.2014.12.034. Epub 2015 Feb 16. PubMed PMID: 25752567.

12: Masoodi M, Talebi-Taher M, Tabatabaie K, Khaleghi S, Faghihi AH, Agah S, Asadi R. Clarithromycin vs. Gemifloxacin in Quadruple Therapy Regimens for Empiric Primary Treatment of Helicobacter pylori Infection: A Randomized Clinical Trial. Middle East J Dig Dis. 2015 Apr;7(2):88-93. PubMed PMID: 26106468; PubMed Central PMCID: PMC4430797.

13: Hassan SS, Hayat U, Tariq I, Ahmad I, Hayat MM, Uzair M, Ansari MT. Spectrophotometric method for the determination of Gemifloxacin mesylate in pure and tablet dosage form. Pak J Pharm Sci. 2014 Sep;27(5):1171-4. PubMed PMID: 25176374.

14: de Araújo BV, Laureano JV, Grünspan LD, Dalla Costa T, Tasso L. Validation of an efficient LC-microdialysis method for gemifloxacin quantitation in lung, kidney and liver of rats. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Mar 1;919-920:62-6. doi: 10.1016/j.jchromb.2013.01.006. Epub 2013 Jan 14. PubMed PMID: 23411020.

15: Al-Tamimi SA, Alarfaj NA, Aly FA, Al-Mohaimeed AM. Spectrofluorimetric analysis of gemifloxacin mesylate in pharmaceutical formulations. Luminescence. 2014 Mar;29(2):127-31. doi: 10.1002/bio.2515. Epub 2013 May 17. PubMed PMID: 23681953.

16: Moussa BA, Mahrouse MA, Hassan MA, Fawzy MG. Spectrofluorimetric determination of gemifloxacin mesylate and linezolid in pharmaceutical formulations: Application of quinone-based fluorophores and enhanced native fluorescence. Acta Pharm. 2014 Mar;64(1):15-28. doi: 10.2478/acph-2014-0005. PubMed PMID: 24670349.

17: Paim CS, Führ F, Miron DS, Steppe M, Schapoval EE. Highly selective colorimetric method to determine gemifloxacin mesylate in the presence of a synthetic impurity. J AOAC Int. 2014 Jan-Feb;97(1):94-8. PubMed PMID: 24672864.

18: Chang WL, Kao CY, Wu CT, Huang AH, Wu JJ, Yang HB, Cheng HC, Sheu BS. Gemifloxacin can partially overcome quinolone resistance of H. pylori with gyrA mutation in Taiwan. Helicobacter. 2012 Jun;17(3):210-5. doi: 10.1111/j.1523-5378.2012.00935.x. Epub 2012 Mar 20. PubMed PMID: 22515359.

19: El-Koussi WM, Atia NN, Mahmoud AM, El-Shabouri SR. HPTLC method for direct determination of gemifloxacin mesylate in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Sep 15;967:98-101. doi: 10.1016/j.jchromb.2014.07.004. Epub 2014 Jul 11. PubMed PMID: 25086419.

20: Paim CS, Führ F, Martins MT, Gnoatto S, Bajerski L, Garcia CV, Steppe M, Schapoval EE. Structural elucidation of gemifloxacin mesylate degradation product. Biomed Chromatogr. 2016 Mar;30(3):459-65. doi: 10.1002/bmc.3569. Epub 2015 Sep 2. PubMed PMID: 26205148.