Garenoxacin mesylate [USAN]
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MedKoo CAT#: 525152

CAS#: 223652-90-2

Description: Garenoxacin mesylate [USAN] is a novel oral des-fluoro quinolone with potent antimicrobial activity against common respiratory pathogens, including resistant strains and Gram-positive and Gram-negative bacterial infections.


Chemical Structure

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Garenoxacin mesylate [USAN]
CAS# 223652-90-2

Theoretical Analysis

MedKoo Cat#: 525152
Name: Garenoxacin mesylate [USAN]
CAS#: 223652-90-2
Chemical Formula: C24H26F2N2O8S
Exact Mass: 540.1378
Molecular Weight: 540.5348
Elemental Analysis: C, 53.33; H, 4.85; F, 7.03; N, 5.18; O, 23.68; S, 5.93

Price and Availability

Size Price Availability Quantity
10.0mg USD 230.0 2 Weeks
50.0mg USD 570.0 2 Weeks
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Synonym: Garenoxacin mesylate [USAN]; BMS-284756-01; Garenoxacin mesylate; Garenoxacin mesylate hydrate; T-3811ME.

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 monomethanesulfonate monohydrate

InChi Key: IGTHEWGRXUAFKF-NVJADKKVSA-N

InChi Code: InChI=1S/C23H20F2N2O4.CH4O3S.H2O/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;1-5(2,3)4;/h2,5-8,10-11,14,23,26H,3-4,9H2,1H3,(H,29,30);1H3,(H,2,3,4);1H2/t11-;;/m1../s1

SMILES Code: C[C@@H]1c2ccc(cc2CN1)c3ccc4c(c3OC(F)F)n(cc(c4=O)C(=O)O)C5CC5.CS(=O)(=O)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

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

Product Data:

Biological target: Garenoxacin Mesylate hydrate (BMS284756 Mesylate hydrate) is a novel oral des-fluoro(6) quinolone with potent antimicrobial activity, against common respiratory pathogens, including resistant strains.
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 185.0
Water 12.5 23.13

Preparing Stock Solutions

The following data is based on the product molecular weight 540.5348 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. 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: 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.
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.

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1: Takagi H, Tanaka K, Tsuda H, Kobayashi H. Clinical studies of garenoxacin. Int J Antimicrob Agents. 2008 Dec;32(6):468-74. doi: 10.1016/j.ijantimicag.2008.06.032. Epub 2008 Sep 13. Review. PubMed PMID: 18790608.