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MedKoo Cat#: 314248 | Name: Tedizolid phosphate
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Description:

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

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.

Chemical Structure

Tedizolid phosphate
Tedizolid phosphate
CAS#856867-55-5 (phosphate)

Theoretical Analysis

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

Price and Availability

Size Price Availability Quantity
100mg USD 150.00 Ready to ship
1g USD 450.00 Ready to ship
2g USD 750.00 Ready to ship
5g USD 1,650.00 Ready to ship
10g USD 2,950.00 2 Weeks
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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
More Info
Biological target:
Tedizolid phosphate (TR-701FA) is a novel oxazolidinone with activity against Gram-positive pathogens.
In vitro activity:
Susceptibilities to TZD (Tedizolid) and LZD were correlated with a Spearman correlation coefficient of 0.78 (P < .001), implying that strains with a high LZD MIC were likely to also display a high TZD MIC. According to CLSI interpretive criteria, 23% and 34% of isolates were susceptible (MIC ≤8 μg/mL) and intermediate (MIC = 16 μg/mL) to LZD, respectively. No interpretive criteria are currently available for TZD. Comparison of strains with a rough or a smooth colony morphotype revealed a significant 2-fold difference in the TZD MICs (median MICs of 2 and 4 μg/ml for the rough and smooth morphotype, respectively; P = 6 × 10−4, Mann–Whitney U test). Reference: Diagn Microbiol Infect Dis. 2018 Mar;90(3):186-189. https://pubmed.ncbi.nlm.nih.gov/29217419/
In vivo activity:
As shown in Figure 2, groups of untreated WIS 423- or WIS 441-infected worms displayed very low survival rates (≤30%). WIS 423-infected worms injected with tedizolid showed 90% survival at Day 2 and 80% at Day 6, similar to the percentages seen for those injected with linezolid and vancomycin (Figure 2a). Interestingly, tedizolid was more effective than linezolid against strain WIS 441, which exhibited a tedizolid MIC of 2 mg/L. Vancomycin was included as a control reference, displaying 80% survival of WIS 423-infected worms and 70%–80% of WIS 441-infected worms at Day 6 (Figure 2b). These data strongly suggest that tedizolid may represent an efficacious option for the treatment of CF-MRSA infections including those with MRSA strains such as WIS 441 with borderline tedizolid MIC of 2 mg/L. Reference: J Antimicrob Chemother. 2020 Jan; 75(1): 126–134. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7850011/
Solvent mg/mL mM
Solubility
DMSO 29.0 64.40
PBS (pH 7.2) 1.0 2.22
Water 0.1 0.22
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 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.

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. Compain F, Soroka D, Heym B, Gaillard JL, Herrmann JL, Dorchène D, Arthur M, Dubée V. In vitro activity of tedizolid against the Mycobacterium abscessus complex. Diagn Microbiol Infect Dis. 2018 Mar;90(3):186-189. doi: 10.1016/j.diagmicrobio.2017.11.001. Epub 2017 Nov 10. PMID: 29217419. 2. Ract P, Piau-Couapel C, Compain F, Auzou M, Michon J, Cattoir V. In vitro activity of tedizolid and comparator agents against Gram-positive pathogens responsible for bone and joint infections. J Med Microbiol. 2017 Oct;66(10):1374-1378. doi: 10.1099/jmm.0.000595. Epub 2017 Sep 18. PMID: 28920854. 3. Roch M, Varela MC, Taglialegna A, Rosato AE. Tedizolid is a promising antimicrobial option for the treatment of Staphylococcus aureus infections in cystic fibrosis patients. J Antimicrob Chemother. 2020 Jan 1;75(1):126-134. doi: 10.1093/jac/dkz418. PMID: 31617901; PMCID: PMC7850011. 4. Yamagishi Y, Mikamo H, Kato H, Nishiyama N, Asai N, Koizumi Y, Sakanashi D, Suematsu H, Matsuura K, Hagihara M. Efficacy of tedizolid against methicillin-resistant Staphylococcus aureus and Peptostreptococcus anaerobius in thigh mixed-infection mouse model. J Infect Chemother. 2017 Jun;23(6):368-373. doi: 10.1016/j.jiac.2017.02.013. Epub 2017 Mar 23. PMID: 28343752.
In vitro protocol:
1. Compain F, Soroka D, Heym B, Gaillard JL, Herrmann JL, Dorchène D, Arthur M, Dubée V. In vitro activity of tedizolid against the Mycobacterium abscessus complex. Diagn Microbiol Infect Dis. 2018 Mar;90(3):186-189. doi: 10.1016/j.diagmicrobio.2017.11.001. Epub 2017 Nov 10. PMID: 29217419. 2. Ract P, Piau-Couapel C, Compain F, Auzou M, Michon J, Cattoir V. In vitro activity of tedizolid and comparator agents against Gram-positive pathogens responsible for bone and joint infections. J Med Microbiol. 2017 Oct;66(10):1374-1378. doi: 10.1099/jmm.0.000595. Epub 2017 Sep 18. PMID: 28920854.
In vivo protocol:
1. Roch M, Varela MC, Taglialegna A, Rosato AE. Tedizolid is a promising antimicrobial option for the treatment of Staphylococcus aureus infections in cystic fibrosis patients. J Antimicrob Chemother. 2020 Jan 1;75(1):126-134. doi: 10.1093/jac/dkz418. PMID: 31617901; PMCID: PMC7850011. 2. Yamagishi Y, Mikamo H, Kato H, Nishiyama N, Asai N, Koizumi Y, Sakanashi D, Suematsu H, Matsuura K, Hagihara M. Efficacy of tedizolid against methicillin-resistant Staphylococcus aureus and Peptostreptococcus anaerobius in thigh mixed-infection mouse model. J Infect Chemother. 2017 Jun;23(6):368-373. doi: 10.1016/j.jiac.2017.02.013. Epub 2017 Mar 23. PMID: 28343752.
1: Liu X, Enoki Y, Taguchi K, Matsumoto K. Development of a pharmacokinetic/pharmacodynamic evaluation model for osteomyelitis and usefulness of tedizolid as an alternative to vancomycin against MRSA osteomyelitis. J Pharm Pharmacol. 2024 Nov 6:rgae124. doi: 10.1093/jpp/rgae124. Epub ahead of print. PMID: 39504578. 2: Liu Q, He D, Wang L, Wu Y, Liu X, Yang Y, Chen Z, Dong Z, Luo Y, Song Y. Efficacy and Safety of Antibiotics in the Treatment of Methicillin-Resistant Staphylococcus aureus (MRSA) Infections: A Systematic Review and Network Meta-Analysis. Antibiotics (Basel). 2024 Sep 10;13(9):866. doi: 10.3390/antibiotics13090866. PMID: 39335039; PMCID: PMC11428633. 3: Coustilleres F, Thillard EM, Khanna RK, Olivereau S, Ouaissi M, Pansu N, Le Lez ML. Severe Optic Neuropathy Induced by Very Prolonged Tedizolid as Suppressive Therapy: Description of a Case Report and Implication for Better Assessment. Open Forum Infect Dis. 2024 Sep 24;11(9):ofae517. doi: 10.1093/ofid/ofae517. PMID: 39329109; PMCID: PMC11425497. 4: Milosevic TV, Vertenoeil G, Vainchenker W, Tulkens PM, Constantinescu SN, Van Bambeke F. Oxazolidinone antibiotics impair ex vivo megakaryocyte differentiation from hematopoietic progenitor cells and their maturation into platelets. Antimicrob Agents Chemother. 2024 Oct 8;68(10):e0053324. doi: 10.1128/aac.00533-24. Epub 2024 Sep 19. PMID: 39297641; PMCID: PMC11460550. 5: Gültekin HE, Aydın HH, Şahiner A, Soylu FE, Şenyiğit Z, Karayıldırım ÇK. In vitro and in vivo evaluation of tedizolid nanoparticle incorporated buccal films for oromucosal infections. Int J Pharm. 2024 Nov 15;665:124688. doi: 10.1016/j.ijpharm.2024.124688. Epub 2024 Sep 16. PMID: 39293576. 6: Fang Y, Clarke LG, Smith BJ, Shah S. Incidence of serotonin syndrome in patients receiving tedizolid and concomitant serotonergic agents. Antimicrob Agents Chemother. 2024 Oct 8;68(10):e0087024. doi: 10.1128/aac.00870-24. Epub 2024 Sep 5. PMID: 39235251; PMCID: PMC11459941. 7: Johnson TM, Rivera CG, Lee G, Zeuli JD. Pharmacology of emerging drugs for the treatment of multi-drug resistant tuberculosis. J Clin Tuberc Other Mycobact Dis. 2024 Jul 27;37:100470. doi: 10.1016/j.jctube.2024.100470. PMID: 39188351; PMCID: PMC11345926. 8: Chen RH, Burke A, Cho JG, Alffenaar JW, Davies Forsman L. New Oxazolidinones for Tuberculosis: Are Novel Treatments on the Horizon? Pharmaceutics. 2024 Jun 17;16(6):818. doi: 10.3390/pharmaceutics16060818. PMID: 38931939; PMCID: PMC11207443. 9: Zhou M, Liu ZL, Liu JY, Wang XB. Tedizolid phosphate alleviates DSS-induced ulcerative colitis by inhibiting senescence of cell and colon tissue through activating AMPK signaling pathway. Int Immunopharmacol. 2024 Jun 30;135:112286. doi: 10.1016/j.intimp.2024.112286. Epub 2024 May 21. PMID: 38776849. 10: Hou J, Xu Q, Zhou L, Chai J, Lin L, Ma C, Zhu Y, Zhang W. Identification of an Enterococcus faecium strain isolated from raw bovine milk co-harbouring the oxazolidinone resistance genes optrA and poxtA in China. Vet Microbiol. 2024 Jun;293:110103. doi: 10.1016/j.vetmic.2024.110103. Epub 2024 May 3. PMID: 38718528. 11: Kirkegaard C, Parramón-Teixidó CJ, Morales-Comas C, Clemente Bautista S, Rivero Deniz J, Fernández-Hidalgo N. Use of oxazolidinones (linezolid or tedizolid) for the treatment of breast infections. A case series from a tertiary referral hospital. Infection. 2024 Aug;52(4):1585-1593. doi: 10.1007/s15010-024-02269-y. Epub 2024 May 1. PMID: 38691231. 12: Yao Z, Xiao Y, Li W, Kong S, Tu H, Guo S, Liu Z, Ma L, Qiao R, Wang S, Chang M, Zhao X, Zhang Y, Xu L, Sun D, Fu X. FDA-Approved Tedizolid Phosphate Prevents Cisplatin-Induced Hearing Loss Without Decreasing Its Anti-tumor Effect. J Assoc Res Otolaryngol. 2024 Jun;25(3):259-275. doi: 10.1007/s10162-024-00945-2. Epub 2024 Apr 15. PMID: 38622383; PMCID: PMC11150367. 13: Valentin B, Tchaparian M, Daran L, Fievet C, Odou P, Loiez C, Migaud H, Décaudin B, Senneville E. Kératodermie aquagénique palmaire secondaire au traitement d’une ostéite chronique par tédizolide : à propos d’un cas [Palmar aquagenic keratoderma secondary to treatment of chronic osteitis with tedizolide: A case report]. Therapie. 2024 Sep-Oct;79(5):614-615. French. doi: 10.1016/j.therap.2024.03.003. Epub 2024 Apr 2. PMID: 38599996. 14: Toyokawa M, Ohana N, Tanno D, Imai M, Takano Y, Ohashi K, Yamashita T, Saito K, Takahashi H, Shimura H. In vitro activity of tedizolid against 43 species of Nocardia species. Sci Rep. 2024 Mar 4;14(1):5342. doi: 10.1038/s41598-024-55916-7. PMID: 38438563; PMCID: PMC10912709. 15: Tebano G, Zaghi I, Baldasso F, Calgarini C, Capozzi R, Salvadori C, Cricca M, Cristini F. Antibiotic Resistance to Molecules Commonly Prescribed for the Treatment of Antibiotic-Resistant Gram-Positive Pathogens: What Is Relevant for the Clinician? Pathogens. 2024 Jan 19;13(1):88. doi: 10.3390/pathogens13010088. PMID: 38276161; PMCID: PMC10819222. 16: Nau R, Seele J, Eiffert H. New Antibiotics for the Treatment of Nosocomial Central Nervous System Infections. Antibiotics (Basel). 2024 Jan 7;13(1):58. doi: 10.3390/antibiotics13010058. PMID: 38247617; PMCID: PMC10812395. 17: Stellern JJ, Plaisted J, Welles C. Disseminated nocardiosis with persistent neurological disease. BMJ Case Rep. 2024 Jan 9;17(1):e257935. doi: 10.1136/bcr-2023-257935. PMID: 38195189; PMCID: PMC10806866. 18: Yokota K, Kawakami K. Efficacy and side-effect profile of tedizolid in the treatment of streptococcal toxic shock syndrome due to clindamycin-resistant Streptococcus pyogenes: A case report. J Infect Chemother. 2024 Aug;30(8):785-788. doi: 10.1016/j.jiac.2024.01.002. Epub 2024 Jan 6. PMID: 38185364. 19: Staudacher M, Hotz JF, Kriz R, Schefberger K, Schneider L, Spettel K, Starzengruber P, Hagemann JB, Leutzendorff A, Burgmann H, Lagler H. Differences in oxazolidinone resistance mechanisms and small colony variants emergence of Staphylococcus aureus induced in an in vitro resistance development model. Emerg Microbes Infect. 2024 Dec;13(1):2292077. doi: 10.1080/22221751.2023.2292077. Epub 2024 Feb 6. PMID: 38055244; PMCID: PMC10849000. 20: Jung E, Gademann K. Clinically Approved Antibiotics from 2010 to 2022. Chimia (Aarau). 2023 Apr 26;77(4):230-234. doi: 10.2533/chimia.2023.230. PMID: 38047802.