WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 314248
CAS#: 856867-55-5 (phosphate)
Description: Tedizolid phosphate, also know as TR-701FA tedizolid, torezolid (trade name Sivextro), is an oxazolidinone drug being developed by Cubist Pharmaceuticals following acquisition of Trius Therapeutics (originator: Dong-A Pharmaceuticals) for complicated skin and skin-structure infections (cSSSIs), including those caused by methicillin-resistant Staphylococcus aureus (MRSA). Tedizolid has been approved by the FDA on June 20, 2014, for the treatment of MRSA skin infections.
MedKoo Cat#: 314248
Name: Tedizolid phosphate
CAS#: 856867-55-5 (phosphate)
Chemical Formula: C17H16FN6O6P
Exact Mass: 450.0853
Molecular Weight: 450.32
Elemental Analysis: C, 45.34; H, 3.58; F, 4.22; N, 18.66; O, 21.32; P, 6.88
Related CAS #: 856867-39-5 (disodium) 856867-55-5 (phosphate) 856866-72-3
Synonym: TR701-FA; TR-701-FA; TR 701-FA; torezolid; tedizolid phosphate; trade name Sivextro.
IUPAC/Chemical Name: (R)-(3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl dihydrogen phosphate
InChi Key: QCGUSIANLFXSGE-GFCCVEGCSA-N
InChi Code: InChI=1S/C17H16FN6O6P/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)/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
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
The following data is based on the product molecular weight 450.32 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 |
1: 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. PubMed PMID: 25525633.
2: Sahm DF, Deane J, Bien PA, Locke JB, Zuill DE, Shaw KJ, Bartizal KF. Results of the Surveillance of Tedizolid Activity and Resistance Program: in vitro susceptibility of Gram-positive pathogens collected in 2011 and 2012 from the United States and Europe. Diagn Microbiol Infect Dis. 2015 Feb;81(2):112-8. doi: 10.1016/j.diagmicrobio.2014.08.011. Epub 2014 Aug 30. PubMed PMID: 25488274.
3: 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.
4: Shorr AF, Lodise TP, Corey GR, De Anda C, Fang E, Das AF, Prokocimer P. Analysis of the Phase 3 ESTABLISH Trials of Tedizolid versus Linezolid in Acute Bacterial Skin and Skin Structure Infections. Antimicrob Agents Chemother. 2015 Feb;59(2):864-71. doi: 10.1128/AAC.03688-14. Epub 2014 Nov 24. PubMed PMID: 25421472.
5: Jones RN, Holliday NM, Rhomberg PR. Validation of a commercial dry-form broth microdilution device (sensititre) for testing tedizolid, a new oxazolidinone. J Clin Microbiol. 2015 Feb;53(2):657-9. doi: 10.1128/JCM.02769-14. Epub 2014 Nov 19. PubMed PMID: 25411167.
6: Schlosser MJ, Hosako H, Radovsky A, Butt MT, Draganov D, Vija J, Oleson F. Lack of neuropathological changes in rats administered tedizolid phosphate for nine months. Antimicrob Agents Chemother. 2015 Jan;59(1):475-81. doi: 10.1128/AAC.03950-14. Epub 2014 Nov 10. PubMed PMID: 25385101; PubMed Central PMCID: PMC4291389.
7: 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.
8: Flanagan S, McKee EE, Das D, Tulkens PM, Hosako H, Fiedler-Kelly J, Passarell J, Radovsky A, Prokocimer P. Nonclinical and pharmacokinetic assessments to evaluate the potential of tedizolid and linezolid to affect mitochondrial function. Antimicrob Agents Chemother. 2015 Jan;59(1):178-85. doi: 10.1128/AAC.03684-14. Epub 2014 Oct 20. PubMed PMID: 25331703; PubMed Central PMCID: PMC4291347.
9: Rybak JM, Marx K, Martin CA. Early experience with tedizolid: clinical efficacy, pharmacodynamics, and resistance. Pharmacotherapy. 2014 Nov;34(11):1198-208. doi: 10.1002/phar.1491. Epub 2014 Sep 30. PubMed PMID: 25266820.
10: Lodise TP, Fang E, Minassian SL, Prokocimer PG. Platelet profile in patients with acute bacterial skin and skin structure infections receiving tedizolid or linezolid: findings from the Phase 3 ESTABLISH clinical trials. Antimicrob Agents Chemother. 2014 Dec;58(12):7198-204. doi: 10.1128/AAC.03509-14. Epub 2014 Sep 22. PubMed PMID: 25246392; PubMed Central PMCID: PMC4249542.
11: Zurenko G, Bien P, Bensaci M, Patel HN, Thorne G. Use of linezolid susceptibility test results as a surrogate for the susceptibility of Gram-positive pathogens to tedizolid, a novel oxazolidinone. Ann Clin Microbiol Antimicrob. 2014 Sep 20;13:46. doi: 10.1186/s12941-014-0046-0. PubMed PMID: 25238753; PubMed Central PMCID: PMC4291835.
12: 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.
13: Flanagan S, Passarell J, Lu Q, Fiedler-Kelly J, Ludwig E, Prokocimer P. Tedizolid population pharmacokinetics, exposure response, and target attainment. Antimicrob Agents Chemother. 2014 Nov;58(11):6462-70. doi: 10.1128/AAC.03423-14. Epub 2014 Aug 18. PubMed PMID: 25136028; PubMed Central PMCID: PMC4249359.
14: 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.
15: Chen H, Yang Q, Zhang R, He W, Ma X, Zhang J, Xia F, Zhao F, Cao J, Liu Y, Wu W, Hu D, Wang Q, Zhao C, Zhang F, Wang X, Wang Z, Li H, Wang H. In vitro antimicrobial activity of the novel oxazolidinone tedizolid and comparator agents against Staphylococcus aureus and linezolid-resistant Gram-positive pathogens: a multicentre study in China. Int J Antimicrob Agents. 2014 Sep;44(3):276-7. doi: 10.1016/j.ijantimicag.2014.05.007. Epub 2014 Jun 23. PubMed PMID: 25108879.
16: 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.
17: Moran GJ, Fang E, Corey GR, Das AF, De Anda C, Prokocimer P. Tedizolid for 6 days versus linezolid for 10 days for acute bacterial skin and skin-structure infections (ESTABLISH-2): a randomised, double-blind, phase 3, non-inferiority trial. Lancet Infect Dis. 2014 Aug;14(8):696-705. doi: 10.1016/S1473-3099(14)70737-6. Epub 2014 Jun 5. PubMed PMID: 24909499.
18: 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.
19: 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.
20: Kisgen JJ, Mansour H, Unger NR, Childs LM. Tedizolid: a new oxazolidinone antimicrobial. Am J Health Syst Pharm. 2014 Apr 15;71(8):621-33. doi: 10.2146/ajhp130482. Review. PubMed PMID: 24688035.
