Gatifloxacin sesquihydrate

Names

[ Name ]:
Gatifloxacin sesquihydrate

[Synonym ]:
1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-8-METHOXY-7-(3-METHYLPIPERAZIN-1-YL)-4-OXO-3-QUINOLINECARBOXYLIC ACID
Gatifloxacin formic acid ethyl ester
3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-, hydrate (2:3)
Gatifloxacin (300 mg)
TEQUIN
UNII:L4618BD7KJ
1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid trihydrate
Gatifloxacin Tablet
Gatifloxacin Monohydrate
1-Cyclopropyl-6-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-3-quinolinecarboxylic acid
Gatifloxacin sesquihydrate
1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid hydrate (2:3)

Biological Activity

[Description]:

Gatifloxacin sesquihydrate (AM-1155; BMS-206584; PD135432) is a potent fluoroquinolone antibiotic with broad-spectrum antibacterial activity. Gatifloxacin sesquihydrate inhibits bacterial type II topoisomerases (IC50=13.8 μg/ml for S. aureus topoisomerase IV) and E. coli DNA gyrase (IC50 = 0.109 μg/ml)[1]. Gatifloxacin sesquihydrate can be used to treat bacterial conjunctivitis in vivo.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Topoisomerase II:36.7 μM (IC50)

[In Vitro]

Gatifloxacin sesquihydrate is against S. aureus MS5935 topoisomerase IV, E. coli NIHJ JC-2 DNA gyrase and HeLa cell topoisomerase II with IC50 values of 13.8 μg/ml, 0.109 μg/ml, and 265 μg/ml, respectively[1]. Gatifloxacin sesquihydrate is against S. aureus MS5935 topoisomerase IV, E. coli NIHJ JC-2 DNA gyrase and HeLa cell topoisomerase II with MIC values of 0.05 μg/ml, 0.0063 μg/ml, and 122 μg/ml, respectively[1]. Gatifloxacin sesquihydrate exhibits antibacterial activities for wild-type strains (MS5935, MS5952, MR5867 and MR6009) the first-, second-, third-, and fourth-step mutants with MIC values of 0.05 to 0.10 μg/ml, 0.20 μg/ml, 1.56 to 3.13 μg/ml, 1.56 to 6.25 μg/ml, and 50 to 200 μg/ml, respectively. Gatifloxacin sesquihydrate displays the most potent activity against the second- and third-step mutants (MS5952, MR5867 and MR6009) except for the second-step mutant of strain MS5935[2]. Gatifloxacin sesquihydrate has potent activity against norA transformant NY12 (MIC, 0.39 μg/ml)[2]. Gatifloxacin sesquihydrate (20-100 μM; 72 hours) significantly decreases insulin content to 60% at Day 1, and continues to be reduced to 50.1% and 44.7% at Day 3 by 20 μM and 100 μM Gatifloxacin sesquihydrate, respectively[3].

[In Vivo]

Gatifloxacin sesquihydrate (subcutaneous injection; 100 mg/kg; 3 times a day; 30 days) significantly decreases the number of lesions in mouse footpad with Nocardia brasiliensis[4]. Animal Model: Female BALB/c mice with Nocardia brasiliensis in the right hind footpad[4] Dosage: 100 mg/kg Administration: Subcutaneous injection; 3 times a day; 30 days Result: Reduced the production of lesions in mice.

[References]

[1]. Takei M, et al. Inhibitory activities of Gatifloxacin mesylate (AM-1155), a newly developed fluoroquinolone, against bacterial and mammalian type II topoisomerases.Antimicrob Agents Chemother. 1998 Oct;42(10):2678-81.

[2]. Fukuda H, et al. Antibacterial activity of Gatifloxacin mesylate (AM-1155, CG5501, BMS-206584), a newly developed fluoroquinolone, against sequentially acquired quinolone-resistant mutants and the norA transformant of Staphylococcus aureus. Antimicrob Agents Chemother. 1998 Aug;42(8):1917-22.

[3]. Yamada C, et al. Gatifloxacin mesylate acutely stimulates insulin secretion and chronically suppresses insulin biosynthesis. Eur J Pharmacol. 2006 Dec 28;553(1-3):67-72. Epub 2006 Sep 28.

[4]. Daw-Garza A, et al. In vivo therapeutic effect of Gatifloxacin mesylate on BALB/c mice infected with Nocardia brasiliensis.Antimicrob Agents Chemother. 2008 Apr;52(4):1549-50.

Chemical & Physical Properties

[ Density]:
1.386 g/cm3

[ Boiling Point ]:
607.8ºC at 760 mmHg

[ Molecular Formula ]:
C₁₉H₂₂FN₃O_4.3/₂H₂O

[ Molecular Weight ]:
804.834

[ Flash Point ]:
321.4ºC

[ Exact Mass ]:
804.350586

[ PSA ]:
195.29000

[ LogP ]:
4.55550

[ Vapour Pressure ]:
6.43E-23mmHg at 25°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302 + H312 + H332

[ Precautionary Statements ]:
P261-P280-P301 + P312 + P330

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
20/21/22

[ Safety Phrases ]:
36/37

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%