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MedKoo Cat#: 581141 | Name: Tedizolid phosphate disodium salt

Description:

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

Tedizolid phosphate is a novel antibacterial prodrug with potent activity against Gram-positive pathogens. In vitro and in vivo studies demonstrated that the prodrug is rapidly converted by nonspecific phosphatases to the biologically active moiety tedizolid. Tedizolid phosphate is a next-generation oxazolidinone with activity against both methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus spp. Tedizolid has consistently shown potency advantages over linezolid against Gram-positive microorganisms including those with reduced susceptibility to linezolid. Of particular significance, minimum inhibitory concentrations of tedizolid appear to be largely unaffected by the chloramphenicol-florfenicol resistance (cfr) gene, which has been implicated in a number of published linezolid-resistant organism outbreaks.

Chemical Structure

Tedizolid phosphate disodium salt
Tedizolid phosphate disodium salt
CAS#856867-39-5

Theoretical Analysis

MedKoo Cat#: 581141

Name: Tedizolid phosphate disodium salt

CAS#: 856867-39-5

Chemical Formula: C17H14FN6Na2O6P

Exact Mass: 494.0492

Molecular Weight: 494.29

Elemental Analysis: C, 41.31; H, 2.86; F, 3.84; N, 17.00; Na, 9.30; O, 19.42; P, 6.27

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Tedizolid phosphate disodium salt; DA 7218; TR 701; Torezolid phosphate sodium salt; TR-701;
IUPAC/Chemical Name
2-Oxazolidinone, 3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl)phenyl)-5-((phosphonooxy)methyl)-, disodium salt, (5R)-
InChi Key
UAIJRGWLKLRQAH-CURYUGHLSA-L
InChi Code
InChI=1S/C17H16FN6O6P.2Na/c1-23-21-16(20-22-23)15-5-2-10(7-19-15)13-4-3-11(6-14(13)18)24-8-12(30-17(24)25)9-29-31(26,27)28;;/h2-7,12H,8-9H2,1H3,(H2,26,27,28);;/q;2*+1/p-2/t12-;;/m1../s1
SMILES Code
O=C1O[C@@H](COP([O-])([O-])=O)CN1C2=CC=C(C3=CC=C(C4=NN(C)N=N4)N=C3)C(F)=C2.[Na+].[Na+]
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 494.29 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
1: Prokocimer P, De Anda C, Fang E, Mehra P, Das A. Tedizolid phosphate vs linezolid for treatment of acute bacterial skin and skin structure infections: the ESTABLISH-1 randomized trial. JAMA. 2013 Feb 13;309(6):559-69. doi: 10.1001/jama.2013.241. PubMed PMID: 23403680. 2: Chan LC, Basuino L, Dip EC, Chambers HF. Comparative efficacies of tedizolid phosphate, vancomycin, and daptomycin in a rabbit model of methicillin-resistant Staphylococcus aureus endocarditis. Antimicrob Agents Chemother. 2015;59(6):3252-6. doi: 10.1128/AAC.04376-14. Epub 2015 Mar 23. PubMed PMID: 25801564; PubMed Central PMCID: PMC4432129. 3: O'Riordan W, Green S, Mehra P, De Anda C, Fang E, Prokocimer P. Tedizolid phosphate for the management of acute bacterial skin and skin structure infections: efficacy summary. Clin Infect Dis. 2014 Jan;58 Suppl 1:S43-50. doi: 10.1093/cid/cit617. Review. PubMed PMID: 24343832. 4: Gras J. Tedizolid phosphate for the treatment of acute bacterial skin and skin structure infections. Drugs Today (Barc). 2014 Nov;50(11):729-37. doi: 10.1358/dot.2014.50.11.2233783. Review. PubMed PMID: 25525633. 5: Kennedy G, Osborn J, Flanagan S, Alsayed N, Bertolami S. Stability of Crushed Tedizolid Phosphate Tablets for Nasogastric Tube Administration. Drugs R D. 2015 Dec;15(4):329-33. doi: 10.1007/s40268-015-0108-6. PubMed PMID: 26416654; PubMed Central PMCID: PMC4662946. 6: Ong V, Flanagan S, Fang E, Dreskin HJ, Locke JB, Bartizal K, Prokocimer P. Absorption, distribution, metabolism, and excretion of the novel antibacterial prodrug tedizolid phosphate. Drug Metab Dispos. 2014 Aug;42(8):1275-84. doi: 10.1124/dmd.113.056697. Epub 2014 May 29. PubMed PMID: 24875463. 7: Das D, Tulkens PM, Mehra P, Fang E, Prokocimer P. Tedizolid phosphate for the management of acute bacterial skin and skin structure infections: safety summary. Clin Infect Dis. 2014 Jan;58 Suppl 1:S51-7. doi: 10.1093/cid/cit618. Review. PubMed PMID: 24343833. 8: Rybak JM, Roberts K. Tedizolid Phosphate: a Next-Generation Oxazolidinone. Infect Dis Ther. 2015 Feb 24. [Epub ahead of print] PubMed PMID: 25708156; PubMed Central PMCID: PMC4363212. 9: Hall RG 2nd, Michaels HN. Profile of tedizolid phosphate and its potential in the treatment of acute bacterial skin and skin structure infections. Infect Drug Resist. 2015 Apr 22;8:75-82. doi: 10.2147/IDR.S56691. eCollection 2015. Review. PubMed PMID: 25960671; PubMed Central PMCID: PMC4411017. 10: Urbina O, Ferrández O, Espona M, Salas E, Ferrández I, Grau S. Potential role of tedizolid phosphate in the treatment of acute bacterial skin infections. Drug Des Devel Ther. 2013 Apr 3;7:243-65. doi: 10.2147/DDDT.S30728. Print 2013. Review. PubMed PMID: 23589680; PubMed Central PMCID: PMC3622392. 11: Choi S, Im W, Bartizal K. Activity of tedizolid phosphate (TR-701) in murine models of infection with penicillin-resistant and penicillin-sensitive Streptococcus pneumoniae. Antimicrob Agents Chemother. 2012 Sep;56(9):4713-7. doi: 10.1128/AAC.00346-12. Epub 2012 Jun 19. PubMed PMID: 22713339; PubMed Central PMCID: PMC3421900. 12: Hussar DA, Nguyen A. Dalbavancin, tedizolid phosphate, oritavancin diphosphate, and vedolizumab. J Am Pharm Assoc (2003). 2014 Nov-Dec;54(6):658-62. doi: 10.1331/JAPhA.2014.14543. PubMed PMID: 25379985. 13: Flanagan S, Minassian SL, Morris D, Ponnuraj R, Marbury TC, Alcorn HW, Fang E, Prokocimer P. Pharmacokinetics of tedizolid in subjects with renal or hepatic impairment. Antimicrob Agents Chemother. 2014 Nov;58(11):6471-6. doi: 10.1128/AAC.03431-14. Epub 2014 Aug 18. PubMed PMID: 25136024; PubMed Central PMCID: PMC4249404. 14: Lodise TP, Drusano GL. Use of pharmacokinetic/pharmacodynamic systems analyses to inform dose selection of tedizolid phosphate. Clin Infect Dis. 2014 Jan;58 Suppl 1:S28-34. doi: 10.1093/cid/cit615. Review. PubMed PMID: 24343829. 15: Burdette SD, Trotman R. Tedizolid: The First Once-Daily Oxazolidinone Class Antibiotic. Clin Infect Dis. 2015 Oct 15;61(8):1315-21. doi: 10.1093/cid/civ501. Epub 2015 Jun 23. Review. PubMed PMID: 26105167. 16: Ghazi I, Hamada Y, Nicolau DP. Physical compatibility of tedizolid phosphate with selected i.v. drugs during simulated Y-site administration. Am J Health Syst Pharm. 2016 Nov 1;73(21):1769-1776. PubMed PMID: 27769972. 17: Cada DJ, Ingram K, Baker DE. Tedizolid phosphate. Hosp Pharm. 2014 Nov;49(10):961-71. doi: 10.1310/hpj4910-961. PubMed PMID: 25477569; PubMed Central PMCID: PMC4252220. 18: Wong E, Rab S. Tedizolid phosphate (sivextro): a second-generation oxazolidinone to treat acute bacterial skin and skin structure infections. P T. 2014 Aug;39(8):555-79. PubMed PMID: 25136252; PubMed Central PMCID: PMC4123804. 19: Flanagan S, Fang E, Muñoz KA, Minassian SL, Prokocimer PG. Single- and multiple-dose pharmacokinetics and absolute bioavailability of tedizolid. Pharmacotherapy. 2014 Sep;34(9):891-900. doi: 10.1002/phar.1458. Epub 2014 Jul 3. PubMed PMID: 24989138; PubMed Central PMCID: PMC4260119. 20: Molina-Torres CA, Barba-Marines A, Valles-Guerra O, Ocampo-Candiani J, Cavazos-Rocha N, Pucci MJ, Castro-Garza J, Vera-Cabrera L. Intracellular activity of tedizolid phosphate and ACH-702 versus Mycobacterium tuberculosis infected macrophages. Ann Clin Microbiol Antimicrob. 2014 Apr 4;13:13. doi: 10.1186/1476-0711-13-13. PubMed PMID: 24708819; PubMed Central PMCID: PMC3986449.

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