Gatifloxacin A fluoroquinolone antibiotic and inhibitor of type II bacterial topoisomerases

Gatifloxacin (CAS 112811-59-3)

Gatifloxacin | CAS 112811-59-3 is rated 5.0 out of 5 by 1.
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Synonym: Tequin; AM-1155; 1-cyclopropyl-6-fluoranyl-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxidanylidene-quinoline-3-carboxylic acid
Application: A fluoroquinolone antibiotic and inhibitor of type II bacterial topoisomerases
CAS Number: 112811-59-3
Purity: ≥98%
Molecular Weight: 375.4
Molecular Formula: C19H22FN3O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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Gatifloxacin is a fluoroquinolone antibiotic, with potent activity against Gram-negative and Gram-positive bacteria. Gatifloxacin also inhibits bacterial topoismerase II (Topo II).


References

1. Bauernfeind, A., et al., 1997. Comparison of the antibacterial activities of the quinolones Bay 12-8039, gatifloxacin (AM 1155), trovafloxacin, clinafloxacin, levofloxacin and ciprofloxacin. The Journal of antimicrobial chemotherapy. 40(5): 639-51. PMID: 9421311
2. Bauernfeind, A., et al., 1997. Comparison of the antibacterial activities of the quinolones Bay 12-8039, gatifloxacin (AM 1155), trovafloxacin, clinafloxacin, levofloxacin and ciprofloxacin. The Journal of antimicrobial chemotherapy. 40(5): 639-51. PMID: 9421311
3. Ednie, L M., et al., 1998. Activities of gatifloxacin compared to those of seven other agents against anaerobic organisms. Antimicrobial agents and chemotherapy. 42(9): 2459-62. PMID: 9736586
4. Ednie, L M., et al., 1998. Activities of gatifloxacin compared to those of seven other agents against anaerobic organisms. Antimicrobial agents and chemotherapy. 42(9): 2459-62. PMID: 9736586
5. Takei, M., et al., 1998. Inhibitory activities of gatifloxacin (AM-1155), a newly developed fluoroquinolone, against bacterial and mammalian type II topoisomerases. Antimicrobial agents and chemotherapy. 42(10): 2678-81. PMID: 9756776
6. Fukuda, H., et al., 1999. Primary targets of fluoroquinolones in Streptococcus pneumoniae. Antimicrobial agents and chemotherapy. 43(2): 410-2. PMID: 9925547
3. Perry, C M., et al., 1999. Gatifloxacin. Drugs. 58(4): 683-96; discussion 697-8. PMID: 10551438
7. Fukuda, H., et al., 2001. Contributions of the 8-methoxy group of gatifloxacin to resistance selectivity, target preference, and antibacterial activity against Streptococcus pneumoniae. Antimicrobial agents and chemotherapy. 45(6): 1649-53. PMID: 11353607
8. Ge, Tian-Fang., et al., 2007. Gatifloxacin affects GLUT1 gene expression and disturbs glucose homeostasis in vitro. European journal of pharmacology. 573(1-3): 70-4. PMID: 17727838
9. Ali, Tauseef., et al., 2007. Gatifloxacin-associated hypoglycemia. The Journal of the Oklahoma State Medical Association. 100(11): 425-8. PMID: 18183859
10. Haerian, Haleh., et al., 2008. Gatifloxacin produces both hypoglycemia and hyperglycemia: a retrospective study. The American journal of the medical sciences. 335(2): 95-8. PMID: 18277115

Appearance :
Crystalline powder
Physical State :
Solid
Solubility :
Soluble in water at pH 2-5 (40-60 mg/ml), chloroform, methanol (Sparingly), DMSO (10 mM), and ethanol (<1 mg/mL).
Storage :
Store at -20° C
Melting Point :
162° C (dec.)
Boiling Point :
607.79° C at 760 mmHg (Predicted)
Density :
1.39 g/cm3 (Predicted)
Refractive Index :
n20D 1.62 (Predicted)
IC50 :
E.coli DNA gyrase: IC50 = 0.11 µg/ml (bacterial type II topoisomerases); S.aureus topoisomerase IV: IC50 = 13.8 µg/ml (bacterial type II topoisomerases); DNA gyrase subunit A: IC50 = 0.5 µM (Escherichia coli K-12); Topoisomerase IV subunit A : IC50 = 1.2 µM (Staphylococcus aureus); DNA gyrase subunit B: IC50 = 0.5 µM (Escherichia coli K-12); V79 : IC50 = 85 ug.mL-1 (Cricetulus griseus)
pK Values :
pKa: 6.43 (Predicted), pKb: 8.72 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
VB1983600
PubChem CID :
5379
Merck Index :
14: 4376
MDL Number :
MFCD00895399
Beilstein Registry :
7445861
SMILES :
CC1CN(CCN1)C2=C(C=C3C(=C2OC)N(C=C(C3=O)C(=O)O)C4CC4)F

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Gatifloxacin  Product Citations

See how others have used Gatifloxacin. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 13 total

PMID: # 28272433  Orfi, Z. et al. 2017. Sci Rep. 7: 44073.

PMID: # 19294528  Cheng, J. et al. 2010. Mol. Biol. Rep. 37: 1261-1267.

PMID: # 19846046  Stella, EJ. et al. 2009. J. Microbiol. Methods. 79: 371-373.

PMID: # 19723585  Elliott, B. et al. 2009. Anaerobe. 15: 249-251.

PMID: # 19781061  Stabler, RA. et al. 2009. Genome Biol. 10: -.

PMID: # 18471639  Ong-Tone, L. et al. 2008. J Cataract Refract Surg. 34: 819-822.

PMID: # 18070980  Peloquin, CA. et al. 2008. Antimicrob. Agents Chemother. 52: 852-857.

PMID: # 18285484  Daw-Garza, A. et al. 2008. Antimicrob. Agents Chemother. 52: 1549-1550.

PMID: # 17645343  Zhao, C. et al. 2007. J. Agric. Food Chem. 55: 6879-6884.

PMID: # 17208455  Majumdar, T. et al. 2007. Fish Shellfish Immunol. 23: 222-230.

Citations 1 to 10 of 13 total
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Rated 5 out of 5 by from Stabler Stabler, RA. et al. (PubMed 19781061) used gatifloxacin, a broad-spectrum antibiotic, against several strains of Clostridium difficile in an effort to explain the emergence of hypervirulent strains of the bacterium. -SCBT Publication Review
Date published: 2015-02-11
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