Garenoxacin | CAS#194804-75-6 | antimicrobial

MedKoo Cat#: 319504 | Name: Garenoxacin

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Description:

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

Garenoxacin is a novel oral des-fluoro(6) quinolone with potent antimicrobial activity against common respiratory pathogens, including resistant strains. It has favourable pharmacokinetic profiles for maximum plasma concentration (Cmax) and area under the plasma concentration-time curve (AUC), with good penetration into sputum and otorhinolaryngological tissues. In clinical studies, the efficacy of Garenoxacin ranged from 92% to 96% in patients with bacterial pneumonia, mycoplasma pneumonia, chlamydial pneumonia and acute bronchitis. Garenoxacin is very effective in treating patients with upper and lower respiratory tract infections.

Chemical Structure

Garenoxacin

CAS#194804-75-6 (free base)

Theoretical Analysis

MedKoo Cat#: 319504

Name: Garenoxacin

CAS#: 194804-75-6 (free base)

Chemical Formula: C23H20F2N2O4

Exact Mass: 426.1391

Molecular Weight: 426.42

Elemental Analysis: C, 64.78; H, 4.73; F, 8.91; N, 6.57; O, 15.01

Price and Availability

Size	Price	Availability
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,250.00	2 Weeks

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Related CAS #

223652-82-2 (mesylate) 194804-75-6 (free base) 223652-90-2 (mesylate hydrate)

Synonym

BMS284756; BMS 284756; BMS-284756; T-3811; T 3811; T3811; Garenoxacin; Garenoxacine; Garenoxacino; Ganefloxacin; Garenfloxacin

IUPAC/Chemical Name

1-Cyclopropyl-8-(difluoromethoxy)-7-[(1R)-1-methyl-2,3-dihydro-1H-isoindol-5-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

InChi Key

NJDRXTDGYFKORP-LLVKDONJSA-N

InChi Code

InChI=1S/C23H20F2N2O4/c1-11-15-5-2-12(8-13(15)9-26-11)16-6-7-17-19(21(16)31-23(24)25)27(14-3-4-14)10-18(20(17)28)22(29)30/h2,5-8,10-11,14,23,26H,3-4,9H2,1H3,(H,29,30)/t11-/m1/s1

SMILES Code

O=C(C1=CN(C2CC2)C3=C(C=CC(C4=CC5=C([C@@H](C)NC5)C=C4)=C3OC(F)F)C1=O)O

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

View handling instruction

Biological target:

Garenoxacin (BMS284756) is a quinolone antibiotic for the treatment of Gram-positive and Gram-negative bacterial infections.

In vitro activity:

Table 1 indicates that garenoxacin was 4 to 16 times more active than levofloxacin against the S. aureus and VGS isolates used in this study. Reference: Antimicrob Agents Chemother. 2004 Jan;48(1):86-92. https://pubmed.ncbi.nlm.nih.gov/14693523/

In vivo activity:

Garenoxacin at 25 and 50 mg/kg was highly effective (survival rates, 85 to 100%) against the wild-type strain and mutants harboring a single mutation. TVA was as effective as garenoxacin against these strains. TVA at 200 mg/kg and garenoxacin at 50 mg/kg were ineffective against the mutant with the parC and gyrA double mutations and the mutant with the gyrA, parC, and parE triple mutations. Reference: Antimicrob Agents Chemother. 2004 Mar;48(3):765-73. https://pubmed.ncbi.nlm.nih.gov/14982762/

	Solvent	mg/mL	mM
Solubility
	DMSO	1.5	3.52

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 426.42 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.

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. Yamamoto K, Yanagihara K, Sugahara K, Imamura Y, Seki M, Izumikawa K, Kakeya H, Yamamoto Y, Hirakata Y, Kamihira S, Kohno S. In vitro activity of garenoxacin against Streptococcus pneumoniae mutants with characterized resistance mechanisms. Antimicrob Agents Chemother. 2009 Aug;53(8):3572-5. doi: 10.1128/AAC.00176-09. Epub 2009 May 18. PMID: 19451290; PMCID: PMC2715604. 2. Entenza JM, Vouillamoz J, Glauser MP, Moreillon P. Efficacy of garenoxacin in treatment of experimental endocarditis due to Staphylococcus aureus or viridans group streptococci. Antimicrob Agents Chemother. 2004 Jan;48(1):86-92. doi: 10.1128/AAC.48.1.86-92.2004. PMID: 14693523; PMCID: PMC310157. 3. Azoulay-Dupuis E, Bédos JP, Mohler J, Peytavin G, Isturiz R, Moine P, Rieux V, Cherbuliez C, Péchère JC, Fantin B, Köhler T. Activities of garenoxacin against quinolone-resistant Streptococcus pneumoniae strains in vitro and in a mouse pneumonia model. Antimicrob Agents Chemother. 2004 Mar;48(3):765-73. doi: 10.1128/AAC.48.3.765-773.2004. PMID: 14982762; PMCID: PMC353052.

In vitro protocol:

In vivo protocol:

1. Azoulay-Dupuis E, Bédos JP, Mohler J, Peytavin G, Isturiz R, Moine P, Rieux V, Cherbuliez C, Péchère JC, Fantin B, Köhler T. Activities of garenoxacin against quinolone-resistant Streptococcus pneumoniae strains in vitro and in a mouse pneumonia model. Antimicrob Agents Chemother. 2004 Mar;48(3):765-73. doi: 10.1128/AAC.48.3.765-773.2004. PMID: 14982762; PMCID: PMC353052.

1: Yamagishi Y, Hagihara M, Hamada Y, Kimura Y, Imai H, Mikamo H. Pharmacokinetic study of garenoxacin in severe renal failure patients. Jpn J Antibiot. 2015 Jun;68(3):141-50. PubMed PMID: 26349115. 2: Hajare A, Gupta A, Patil S, Krishnaprasad K, Bhargava A. A prescription event monitoring study on the utility of garenoxacin, a newer fluoroquinolone in India. Int J Appl Basic Med Res. 2015 May-Aug;5(2):87-91. doi: 10.4103/2229-516X.157151. PubMed PMID: 26097813; PubMed Central PMCID: PMC4456900. 3: Tagawa M, Ochiai S, Nakamura Y, Sato A, Chinushi M. Secondly ECG recordings in the emergency room revealed Garenoxacin-induced abnormal QT interval prolongation in a patient with multiple syncopal attacks. Heart Vessels. 2015 May 29. [Epub ahead of print] PubMed PMID: 26022375. 4: Uni M, Yoshimi A, Yamazaki S, Taoka K, Shinohara A, Nannya Y, Nakamura F, Kurokawa M. Comparison of garenoxacin with levofloxacin as antimicrobial prophylaxis in acute myeloid leukemia. Jpn J Clin Oncol. 2015 Aug;45(8):745-8. doi: 10.1093/jjco/hyv071. Epub 2015 May 19. PubMed PMID: 25989991. 5: Vora A. Garenoxacin. J Assoc Physicians India. 2014 Jan;62(1):34-5. PubMed PMID: 25327090. 6: Hata A, Katakami N, Masuda Y, Takashima K, Takeshita J, Tanaka K, Kaji R, Fujita S, Ose T, Kitajima N. [Comparison of garenoxacin and levofloxacin for the prophylaxis of febrile neutropenia]. Gan To Kagaku Ryoho. 2014 Sep;41(9):1119-23. Japanese. PubMed PMID: 25248895. 7: Pukar MM, Hajare AL, Krishnaprasad K, Bhargava AI. Garenoxacin in Skin and Skin Structure Infections Sustained due to Road Traffic Accident. J Clin Diagn Res. 2014 Jun;8(6):HD01-3. doi: 10.7860/JCDR/2014/9066.4458. Epub 2014 Jun 20. PubMed PMID: 25121004; PubMed Central PMCID: PMC4129297. 8: Izumikawa K, Watanabe A, Miyashita N, Ishida T, Hosono H, Kushimoto S, Kohno S. Efficacy and safety of garenoxacin tablets on bacterial pneumonia: postmarketing surveillance in Japan. J Infect Chemother. 2014 Sep;20(9):549-57. doi: 10.1016/j.jiac.2014.05.003. Epub 2014 Jun 13. PubMed PMID: 24934887. 9: Izumikawa K, Watanabe A, Miyashita N, Ishida T, Hosono H, Kushimoto S, Kohno S. Efficacy and safety of garenoxacin tablets on clinically diagnosed atypical pneumonia: postmarketing surveillance in Japan. J Infect Chemother. 2014 Sep;20(9):541-8. doi: 10.1016/j.jiac.2014.05.002. Epub 2014 Jun 13. PubMed PMID: 24934886. 10: Fukuda Y, Furuya Y, Nozaki Y, Takahata M, Nomura N, Mitsuyama J. Therapeutic effects of garenoxacin in murine experimental secondary pneumonia by Streptococcus pneumoniae after influenza virus infection. Diagn Microbiol Infect Dis. 2014 Feb;78(2):168-71. doi: 10.1016/j.diagmicrobio.2013.11.003. Epub 2013 Nov 14. PubMed PMID: 24321356. 11: Kohno S, Yanagihara K, Yamamoto Y, Tokimatsu I, Hiramatsu K, Higa F, Tateyama M, Fujita J, Kadota J. Early switch therapy from intravenous sulbactam/ampicillin to oral garenoxacin in patients with community-acquired pneumonia: a multicenter, randomized study in Japan. J Infect Chemother. 2013 Dec;19(6):1035-41. doi: 10.1007/s10156-013-0618-5. Epub 2013 May 22. PubMed PMID: 23695232. 12: Miyake M, Oiso N, Yoshinaga E, Kawada A. Fixed drug eruption due to garenoxacin mesilate hydrate. Eur J Dermatol. 2013 Jan-Feb;23(1):111-2. doi: 10.1684/ejd.2012.1892. PubMed PMID: 23400227. 13: Schaumann R, Janssen E, Funke M, Stîngu CS, Genzel GH, Janssen M, Rodloff AC. In vitro activities of levofloxacin, gatifloxacin, moxifloxacin and garenoxacin against Bacteroides fragilis strains evaluated by kill kinetics. J Med Microbiol. 2013 Apr;62(Pt 4):576-81. doi: 10.1099/jmm.0.053280-0. Epub 2013 Jan 14. PubMed PMID: 23319309. 14: Takahata M, Sugiura Y, Shinmura Y, Fukuda Y, Nomura N. Bactericidal activity of garenoxacin against in vitro biofilm formed by nontypeable Haemophilus influenzae. J Infect Chemother. 2013 Jun;19(3):441-6. doi: 10.1007/s10156-012-0502-8. Epub 2012 Oct 23. PubMed PMID: 23089895. 15: Fukushima K, Nakatsubo M, Noda M, Uenami T, Hayama Y, Tsuruta N, Oniki S, Saito Y, Niju T, Ikeda T. Anaphylaxis due to intravenous levofloxacin with tolerance to garenoxacin. Intern Med. 2012;51(13):1769-72. Epub 2012 Jul 1. PubMed PMID: 22790143. 16: Nakatani M, Mizunaga S, Takahata M, Nomura N. Inhibitory activity of garenoxacin against DNA gyrase of Mycoplasma pneumoniae. J Antimicrob Chemother. 2012 Aug;67(8):1850-2. doi: 10.1093/jac/dks140. Epub 2012 Apr 24. PubMed PMID: 22532464. 17: Futakuchi N, Nakatani M, Takahata M, Mitsuyama J. In vitro antichlamydial activity of garenoxacin against Chlamydia trachomatis. J Infect Chemother. 2012 Aug;18(4):428-35. doi: 10.1007/s10156-011-0345-8. Epub 2011 Nov 25. PubMed PMID: 22113367. 18: Fukuda Y, Takahata M, Sugiura Y, Shinmura Y, Nomura N. In vitro pharmacodynamic evaluation of garenoxacin against quinolone-resistant Streptococcus pneumoniae. Int J Antimicrob Agents. 2012 Feb;39(2):163-7. doi: 10.1016/j.ijantimicag.2011.09.021. Epub 2011 Nov 15. PubMed PMID: 22088660. 19: Ito M, Maruyama Y, Murono S, Wakisaka N, Kondo S, Hatano M, Nakanishi S, Miwa T, Yoshizaki T. Efficacy and safety of garenoxacin in the treatment of upper respiratory tract infections. Auris Nasus Larynx. 2012 Oct;39(5):512-8. doi: 10.1016/j.anl.2011.09.004. Epub 2011 Nov 9. PubMed PMID: 22078851. 20: Tanigawara Y, Nozawa K, Tsuda H. Optimal dose finding of garenoxacin based on population pharmacokinetics/pharmacodynamics and Monte Carlo simulation. Eur J Clin Pharmacol. 2012 Jan;68(1):39-53. doi: 10.1007/s00228-011-1095-3. Epub 2011 Jul 28. PubMed PMID: 21796376; PubMed Central PMCID: PMC3249185.