Synonym
RX-1741; RX 1741; RX1741; Radezolid.
IUPAC/Chemical Name
(S)-N-((3-(4'-((((1H-1,2,3-triazol-5-yl)methyl)amino)methyl)-2-fluoro-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide
InChi Key
BTTNOGHPGJANSW-IBGZPJMESA-N
InChi Code
InChI=1S/C22H23FN6O3/c1-14(30)25-12-19-13-29(22(31)32-19)18-6-7-20(21(23)8-18)16-4-2-15(3-5-16)9-24-10-17-11-26-28-27-17/h2-8,11,19,24H,9-10,12-13H2,1H3,(H,25,30)(H,26,27,28)/t19-/m0/s1
SMILES Code
CC(NC[C@H]1CN(C2=CC=C(C3=CC=C(CNCC4=CN=NN4)C=C3)C(F)=C2)C(O1)=O)=O
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
Biological target:
Radezolid is a oxazolidinone antibiotic that is active against Staphylococcus, Chlamydia, and Legionella species, and remains active against Linezolid-resistant strains.
In vitro activity:
RT-PCR confirmed that the expressions of some downregulated biofilm-related proteins were decreased after exposure to radezolid. Radezolid shows robust antibacterial and anti-biofilm activity against Staphylococcus aureus clinical isolates from China when compared with contezolid and linezolid.
Reference: Front Microbiol. 2023 Apr 26;14:1131178. https://pubmed.ncbi.nlm.nih.gov/37180277/
In vivo activity:
In Phase 2 and 3 clinical trials, radezolid showed mild adverse effects against Methicillin-resistant Staphylococcus aureus.
Reference: Expert Opin Drug Saf. 2016;15(4):467-81. https://pubmed.ncbi.nlm.nih.gov/26764972/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
2.0 |
4.56 |
| DMF |
2.0 |
4.56 |
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
438.46
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. Wang C, Xiong Y, Bao C, Wei Y, Wen Z, Cao X, Yu Z, Deng X, Li G, Deng Q. Antibacterial and anti-biofilm activity of radezolid against Staphylococcus aureus clinical isolates from China. Front Microbiol. 2023 Apr 26;14:1131178. doi: 10.3389/fmicb.2023.1131178. PMID: 37180277; PMCID: PMC10169660.
2. Makarov GI, Reshetnikova RV. Investigation of radezolid interaction with non-canonical chloramphenicol binding site by molecular dynamics simulations. J Mol Graph Model. 2021 Jun;105:107902. doi: 10.1016/j.jmgm.2021.107902. Epub 2021 Mar 21. PMID: 33798835.
3. Bassetti M, Righi E. Safety profiles of old and new antimicrobials for the treatment of MRSA infections. Expert Opin Drug Saf. 2016;15(4):467-81. doi: 10.1517/14740338.2016.1142528. Epub 2016 Feb 6. PMID: 26764972.
4. Shaw KJ, Barbachyn MR. The oxazolidinones: past, present, and future. Ann N Y Acad Sci. 2011 Dec;1241:48-70. doi: 10.1111/j.1749-6632.2011.06330.x. PMID: 22191526.
In vitro protocol:
1. Wang C, Xiong Y, Bao C, Wei Y, Wen Z, Cao X, Yu Z, Deng X, Li G, Deng Q. Antibacterial and anti-biofilm activity of radezolid against Staphylococcus aureus clinical isolates from China. Front Microbiol. 2023 Apr 26;14:1131178. doi: 10.3389/fmicb.2023.1131178. PMID: 37180277; PMCID: PMC10169660.
2. Makarov GI, Reshetnikova RV. Investigation of radezolid interaction with non-canonical chloramphenicol binding site by molecular dynamics simulations. J Mol Graph Model. 2021 Jun;105:107902. doi: 10.1016/j.jmgm.2021.107902. Epub 2021 Mar 21. PMID: 33798835.
In vivo protocol:
1. Bassetti M, Righi E. Safety profiles of old and new antimicrobials for the treatment of MRSA infections. Expert Opin Drug Saf. 2016;15(4):467-81. doi: 10.1517/14740338.2016.1142528. Epub 2016 Feb 6. PMID: 26764972.
2. Shaw KJ, Barbachyn MR. The oxazolidinones: past, present, and future. Ann N Y Acad Sci. 2011 Dec;1241:48-70. doi: 10.1111/j.1749-6632.2011.06330.x. PMID: 22191526.
1: Bassetti M, Righi E. Safety profiles of old and new antimicrobials for the treatment of MRSA infections. Expert Opin Drug Saf. 2016 Jan 14. [Epub ahead of print] PubMed PMID: 26764972.
2: Kern WV. [New antibacterial agents on the market and in the pipeline]. Internist (Berl). 2015 Oct 18. [Epub ahead of print] German. PubMed PMID: 26475603.
3: Fulle S, Saini JS, Homeyer N, Gohlke H. Complex long-distance effects of mutations that confer linezolid resistance in the large ribosomal subunit. Nucleic Acids Res. 2015 Sep 18;43(16):7731-43. doi: 10.1093/nar/gkv729. Epub 2015 Jul 21. PubMed PMID: 26202966; PubMed Central PMCID: PMC4652758.
4: Mendes RE, Deshpande LM, Jones RN. Linezolid update: stable in vitro activity following more than a decade of clinical use and summary of associated resistance mechanisms. Drug Resist Updat. 2014 Apr;17(1-2):1-12. doi: 10.1016/j.drup.2014.04.002. Epub 2014 Apr 6. Review. PubMed PMID: 24880801.
5: Saini JS, Homeyer N, Fulle S, Gohlke H. Determinants of the species selectivity of oxazolidinone antibiotics targeting the large ribosomal subunit. Biol Chem. 2013 Nov;394(11):1529-41. doi: 10.1515/hsz-2013-0188. PubMed PMID: 24006327.
6: Bush K. Improving known classes of antibiotics: an optimistic approach for the future. Curr Opin Pharmacol. 2012 Oct;12(5):527-34. doi: 10.1016/j.coph.2012.06.003. Epub 2012 Jun 28. Review. PubMed PMID: 22748801.
7: Sutcliffe JA. Antibiotics in development targeting protein synthesis. Ann N Y Acad Sci. 2011 Dec;1241:122-52. doi: 10.1111/j.1749-6632.2011.06323.x. Review. PubMed PMID: 22191530.
8: Shaw KJ, Barbachyn MR. The oxazolidinones: past, present, and future. Ann N Y Acad Sci. 2011 Dec;1241:48-70. doi: 10.1111/j.1749-6632.2011.06330.x. Review. PubMed PMID: 22191526.
9: Locke JB, Finn J, Hilgers M, Morales G, Rahawi S, G C K, Picazo JJ, Im W, Shaw KJ, Stein JL. Structure-activity relationships of diverse oxazolidinones for linezolid-resistant Staphylococcus aureus strains possessing the cfr methyltransferase gene or ribosomal mutations. Antimicrob Agents Chemother. 2010 Dec;54(12):5337-43. doi: 10.1128/AAC.00663-10. Epub 2010 Sep 13. PubMed PMID: 20837751; PubMed Central PMCID: PMC2981267.
10: Lemaire S, Tulkens PM, Van Bambeke F. Cellular pharmacokinetics of the novel biaryloxazolidinone radezolid in phagocytic cells: studies with macrophages and polymorphonuclear neutrophils. Antimicrob Agents Chemother. 2010 Jun;54(6):2540-8. doi: 10.1128/AAC.01723-09. Epub 2010 Apr 12. PubMed PMID: 20385873; PubMed Central PMCID: PMC2876419.
11: Lemaire S, Kosowska-Shick K, Appelbaum PC, Verween G, Tulkens PM, Van Bambeke F. Cellular pharmacodynamics of the novel biaryloxazolidinone radezolid: studies with infected phagocytic and nonphagocytic cells, using Staphylococcus aureus, Staphylococcus epidermidis, Listeria monocytogenes, and Legionella pneumophila. Antimicrob Agents Chemother. 2010 Jun;54(6):2549-59. doi: 10.1128/AAC.01724-09. Epub 2010 Apr 12. PubMed PMID: 20385852; PubMed Central PMCID: PMC2876393.
