Gatifloxacin
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MedKoo CAT#: 317966

CAS#: 112811-59-3 (free base)

Description: Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family that inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. Gatifloxacin is a fluoroquinolone antibiotic, with potent activity against Gram-negative and Gram-positive bacteria. Bristol-Myers Squibb introduced Gatifloxacin in 1999 under the proprietary name Tequin for the treatment of respiratory tract infections. Allergan produces it in eye-drop formulation under the names Zymar and Zymaxid. In many countries, gatifloxacin is also available as tablets and in various aqueous solutions for intravenous therapy.

Chemical Structure

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Gatifloxacin
CAS# 112811-59-3 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317966
Name: Gatifloxacin
CAS#: 112811-59-3 (free base)
Chemical Formula: C19H22FN3O4
Exact Mass: 375.16
Molecular Weight: 375.400
Elemental Analysis: Chemical Formula: C19H22FN3O4 Exact Mass: 375.15943 Molecular Weight: 375.39408 Elemental Analysis: C, 60.79; H, 5.91; F, 5.06; N, 11.19; O, 17.05

Price and Availability

Size Price Availability Quantity
5g USD 350 2 Weeks
10g USD 550 2 Weeks
25g USD 1150 2 Weeks
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Related CAS #: 112811-59-3 (free base)   180200-66-2 (sesquihydrate)   316819-28-0 (mesyalate)   404858-36-2 (hemihydrate)    

Synonym: Gatifloxacin; Tequin; Zymar; Gatiflo; Zymaxid; AM 1155; AM-1155; BMS-206584; CG 5501; gatifloxacin; gatifloxacine; Tequin; Zymar;

IUPAC/Chemical Name: 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid

InChi Key: XUBOMFCQGDBHNK-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)

SMILES Code: CC1CN(CCN1)C2=C(C=C3C(=C2OC)N(C=C(C3=O)C(=O)O)C4CC4)F

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, not in 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:

Product Data:
Product Data
Instruction:
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Biological target: Gatifloxacin (AM-1155; BMS-206584; PD135432) is a potent fluoroquinolone antibiotic with broad-spectrum antibacterial activity. Gatifloxacin 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).
In vitro activity: In this study, gatifloxacin showed a higher inhibitory activity against S. aureus topoisomerase IV (IC50 = 13.8 μg/ml) and E. coli DNA gyrase (IC50 = 0.109 μg/ml) than did the other quinolones tested, except for clinafloxacin and ciprofloxacin (Table 1). Reference: Antimicrob Agents Chemother. 1998 Oct;42(10):2678-81. https://pubmed.ncbi.nlm.nih.gov/9756776/
In vivo activity: Gatifloxacin at 100 mg/kg maintained plasma levels over the MIC of N. brasiliensis HUJEG-1 (0.25 μg/ml) for more than 4 h, reaching a maximum concentration in serum of 18 μg/ml (Fig. 1). Linezolid at 25 mg/kg also kept concentrations above the MIC (0.12 μg/ml) for more than 4 h, with a maximum concentration in serum of 50 μg/ml. Given these results, this study decided to use gatifloxacin at 100 mg/kg three times daily, injected subcutaneously, and linezolid also three times per day at 25 mg/kg. In Fig. 2, the effect of gatifloxacin on the development of the lesions is shown. The animals showed a decrease in the number of lesions, comparable to the effect of linezolid. Reference: Antimicrob Agents Chemother. 2008 Apr;52(4):1549-50. https://pubmed.ncbi.nlm.nih.gov/18285484/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 26.64
DMF:PBS (pH 7.2) (1:1) 0.5 1.33
DMSO 3.3 8.88
Water 1.0 2.66

Preparing Stock Solutions

The following data is based on the product molecular weight 375.40 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.

Recalculate based on batch purity %
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. Takei M, Fukuda H, Yasue T, Hosaka M, Oomori Y. Inhibitory activities of gatifloxacin (AM-1155), a newly developed fluoroquinolone, against bacterial and mammalian type II topoisomerases. Antimicrob Agents Chemother. 1998 Oct;42(10):2678-81. doi: 10.1128/AAC.42.10.2678. PMID: 9756776; PMCID: PMC105918. 2. Fukuda H, Hori S, Hiramatsu K. Antibacterial activity of gatifloxacin (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. doi: 10.1128/AAC.42.8.1917. PMID: 9687384; PMCID: PMC105710. 3. Daw-Garza A, Welsh O, Said-Fernández S, Lozano-Garza HG, Waksman de Torres N, Rocha NC, Ocampo-Candiani J, Vera-Cabrera L. In vivo therapeutic effect of gatifloxacin on BALB/c mice infected with Nocardia brasiliensis. Antimicrob Agents Chemother. 2008 Apr;52(4):1549-50. doi: 10.1128/AAC.00148-08. Epub 2008 Feb 19. PMID: 18285484; PMCID: PMC2292517. 4. Ambrose PG, Forrest A, Craig WA, Rubino CM, Bhavnani SM, Drusano GL, Heine HS. Pharmacokinetics-pharmacodynamics of gatifloxacin in a lethal murine Bacillus anthracis inhalation infection model. Antimicrob Agents Chemother. 2007 Dec;51(12):4351-5. doi: 10.1128/AAC.00251-07. Epub 2007 Sep 17. PMID: 17875992; PMCID: PMC2167989.
In vitro protocol: 1. Takei M, Fukuda H, Yasue T, Hosaka M, Oomori Y. Inhibitory activities of gatifloxacin (AM-1155), a newly developed fluoroquinolone, against bacterial and mammalian type II topoisomerases. Antimicrob Agents Chemother. 1998 Oct;42(10):2678-81. doi: 10.1128/AAC.42.10.2678. PMID: 9756776; PMCID: PMC105918. 2. Fukuda H, Hori S, Hiramatsu K. Antibacterial activity of gatifloxacin (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. doi: 10.1128/AAC.42.8.1917. PMID: 9687384; PMCID: PMC105710.
In vivo protocol: 1. Daw-Garza A, Welsh O, Said-Fernández S, Lozano-Garza HG, Waksman de Torres N, Rocha NC, Ocampo-Candiani J, Vera-Cabrera L. In vivo therapeutic effect of gatifloxacin on BALB/c mice infected with Nocardia brasiliensis. Antimicrob Agents Chemother. 2008 Apr;52(4):1549-50. doi: 10.1128/AAC.00148-08. Epub 2008 Feb 19. PMID: 18285484; PMCID: PMC2292517. 2. Ambrose PG, Forrest A, Craig WA, Rubino CM, Bhavnani SM, Drusano GL, Heine HS. Pharmacokinetics-pharmacodynamics of gatifloxacin in a lethal murine Bacillus anthracis inhalation infection model. Antimicrob Agents Chemother. 2007 Dec;51(12):4351-5. doi: 10.1128/AAC.00251-07. Epub 2007 Sep 17. PMID: 17875992; PMCID: PMC2167989.

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1: Ruan Q, Liu Q, Sun F, Shao L, Jin J, Yu S, Ai J, Zhang B, Zhang W.
Moxifloxacin and gatifloxacin for initial therapy of tuberculosis: a
meta-analysis of randomized clinical trials. Emerg Microbes Infect. 2016 Feb
24;5:e12. doi: 10.1038/emi.2016.12. PubMed PMID: 26905025.


2: Duxfield L, Sultana R, Wang R, Englebretsen V, Deo S, Swift S, Rupenthal I,
Al-Kassas R. Development of gatifloxacin-loaded cationic polymeric nanoparticles
for ocular drug delivery. Pharm Dev Technol. 2016 Mar;21(2):172-9. doi:
10.3109/10837450.2015.1091839. Epub 2015 Oct 12. PubMed PMID: 26794936.


3: Mimouni M, Geffen N, Rosen E, Segev F. The effect of gatifloxacin 0.3% or
moxifloxacin 0.5% on corneal healing, ocular tolerability and toxicity following
pterygium surgery. Cutan Ocul Toxicol. 2016 Mar;35(1):8-12. doi:
10.3109/15569527.2014.1003266. Epub 2015 Jan 19. PubMed PMID: 25597371.


4: Kalam MA, Alshamsan A, Aljuffali IA, Mishra AK, Sultana Y. Delivery of
gatifloxacin using microemulsion as vehicle: formulation, evaluation,
transcorneal permeation and aqueous humor drug determination. Drug Deliv. 2016
Mar;23(3):896-907. doi: 10.3109/10717544.2014.920432. Epub 2014 May 28. PubMed
PMID: 24865289.


5: Arjyal A, Basnyat B, Nhan HT, Koirala S, Giri A, Joshi N, Shakya M, Pathak KR,
Mahat SP, Prajapati SP, Adhikari N, Thapa R, Merson L, Gajurel D, Lamsal K,
Lamsal D, Yadav BK, Shah G, Shrestha P, Dongol S, Karkey A, Thompson CN, Thieu
NT, Thanh DP, Baker S, Thwaites GE, Wolbers M, Dolecek C. Gatifloxacin versus
ceftriaxone for uncomplicated enteric fever in Nepal: an open-label, two-centre,
randomised controlled trial. Lancet Infect Dis. 2016 Jan 19. pii:
S1473-3099(15)00530-7. doi: 10.1016/S1473-3099(15)00530-7. [Epub ahead of print]
PubMed PMID: 26809813.


6: Sharma N, Arora T, Jain V, Agarwal T, Jain R, Jain V, Yadav CP, Titiyal J,
Satpathy G. Gatifloxacin 0.3% Versus Fortified Tobramycin-Cefazolin in Treating
Nonperforated Bacterial Corneal Ulcers: Randomized, Controlled Trial. Cornea.
2016 Jan;35(1):56-61. doi: 10.1097/ICO.0000000000000664. PubMed PMID: 26509763.


7: Kamruzzaman M, Faruqui AN, Hossain MI, Lee SH. Spectroscopic study of the
interaction between adenosine disodium triphosphate and gatifloxacin-Al3+ complex
and its analytical application. Luminescence. 2015 Nov;30(7):1077-82. doi:
10.1002/bio.2861. Epub 2015 Feb 12. PubMed PMID: 25683636.


8: Wabaidur Sm, Alam SM, Alothman ZA, Mohsin K. Silver nanoparticles enhanced
flow injection chemiluminescence determination of gatifloxacin in pharmaceutical
formulation and spiked urine sample. Spectrochim Acta A Mol Biomol Spectrosc.
2015 Jun 5;144:170-5. doi: 10.1016/j.saa.2015.02.051. Epub 2015 Feb 21. PubMed
PMID: 25754393.


9: Lima Vaz MF, de Oliveira JV, Cassella RJ, Pacheco WF. Development of a
flow-injection analysis system with fluorescence detection for gatifloxacin
determination in organized medium. Luminescence. 2015 May;30(3):337-42. doi:
10.1002/bio.2736. Epub 2014 Jul 24. PubMed PMID: 25060163.


10: A four-month gatifloxacin-containing regimen for treating tuberculosis. N
Engl J Med. 2015 Apr 23;372(17):1677. doi: 10.1056/NEJMx150015. PubMed PMID:
25901444.


11: Kumbhar GB, Khan AM, Rampal S. Evaluation of gatifloxacin for its potential
to induce antioxidant imbalance and retinopathy in rabbits. Hum Exp Toxicol. 2015
Apr;34(4):372-9. doi: 10.1177/0960327114530743. Epub 2014 Jul 15. PubMed PMID:
25028261.


12: Zhang CJ, Lei HT, Huang XL, Liu YJ, Cai K, Xu ZL, Sun YM. Preparative
resolution of gatifloxacin enantiomers with pre-column esterification strategy
and comparing their enantioselectivity to bacteria and antibody. Biomed Environ
Sci. 2015 Feb;28(2):157-60. doi: 10.3967/bes2015.021. PubMed PMID: 25716569.


13: Ding W, Ni W, Chen H, Yuan J, Huang X, Zhang Z, Wang Y, Yu Y, Yao K.
Comparison of Drug Concentrations in Human Aqueous Humor after the Administration
of 0.3% Gatifloxacin Ophthalmic Gel, 0.3% Gatifloxacin and 0.5% Levofloxacin
Ophthalmic Solutions. Int J Med Sci. 2015 Jun 10;12(6):517-23. doi:
10.7150/ijms.11376. eCollection 2015. PubMed PMID: 26078713; PubMed Central
PMCID: PMC4466517.


14: Aljuffali IA, Kalam MA, Sultana Y, Imran A, Alshamsan A. Development and
validation of stability-indicating high performance liquid chromatography method
to analyze gatifloxacin in bulk drug and pharmaceutical preparations. Saudi Pharm
J. 2015 Jan;23(1):85-94. doi: 10.1016/j.jsps.2014.06.005. Epub 2014 Jun 28.
PubMed PMID: 25685047; PubMed Central PMCID: PMC4310989.


15: Heller W, Cruz M, Bhagat YR, De Leon JM, Felix C, Villanueva L, Hollander DA,
Jensen H. Gatifloxacin 0.5% administered twice daily for the treatment of acute
bacterial conjunctivitis in patients one year of age or older. J Ocul Pharmacol
Ther. 2014 Dec;30(10):815-22. doi: 10.1089/jop.2014.0040. PubMed PMID: 25244402.


16: Arthanari S, Mani G, Jang JH, Choi JO, Cho YH, Lee JH, Cha SE, Oh HS, Kwon
DH, Jang HT. Preparation and characterization of gatifloxacin-loaded
alginate/poly (vinyl alcohol) electrospun nanofibers. Artif Cells Nanomed
Biotechnol. 2014 Dec 15:1-6. [Epub ahead of print] PubMed PMID: 25510448.


17: Merle CS, Fielding K, Sow OB, Gninafon M, Lo MB, Mthiyane T, Odhiambo J,
Amukoye E, Bah B, Kassa F, N'Diaye A, Rustomjee R, de Jong BC, Horton J, Perronne
C, Sismanidis C, Lapujade O, Olliaro PL, Lienhardt C; OFLOTUB/Gatifloxacin for
Tuberculosis Project. A four-month gatifloxacin-containing regimen for treating
tuberculosis. N Engl J Med. 2014 Oct 23;371(17):1588-98. doi:
10.1056/NEJMoa1315817. Erratum in: N Engl J Med. 2015 Apr 23;372(17):1677. PubMed
PMID: 25337748.


18: Kłosińska-Szmurło E, Pluciński FA, Grudzień M, Betlejewska-Kielak K,
Biernacka J, Mazurek AP. Experimental and theoretical studies on the molecular
properties of ciprofloxacin, norfloxacin, pefloxacin, sparfloxacin, and
gatifloxacin in determining bioavailability. J Biol Phys. 2014 Sep;40(4):335-45.
doi: 10.1007/s10867-014-9354-z. Epub 2014 Jul 18. PubMed PMID: 25033818; PubMed
Central PMCID: PMC4119185.


19: Kanoujia J, Kushwaha PS, Saraf SA. Evaluation of gatifloxacin pluronic
micelles and development of its formulation for ocular delivery. Drug Deliv
Transl Res. 2014 Aug;4(4):334-43. doi: 10.1007/s13346-014-0194-y. PubMed PMID:
25787066.


20: Shams S, Ali B, Afzal M, Kazmi I, Al-Abbasi FA, Anwar F. Antifungal effect of
Gatifloxacin and copper ions combination. J Antibiot (Tokyo). 2014
Jul;67(7):499-504. doi: 10.1038/ja.2014.35. Epub 2014 Jun 4. PubMed PMID:
24894182.