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ChemicalBook >> CAS DataBase List >>Torezolid

Torezolid

CAS No.
856866-72-3
Chemical Name:
Torezolid
Synonyms
Tedizolid;(R)-3-(3-fluoro-4-(6-(2-Methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxyMethyl)oxazolidin-2-one;Tedizolidted;CS-1826;Tedizolid Impurity 47;DA-7157;DA 7157;Torezolid;Torezolid-21;Torezolid (TR-701
CBNumber:
CB02484972
Molecular Formula:
C17H15FN6O3
Molecular Weight:
370.34
MDL Number:
MFCD19442562
MOL File:
856866-72-3.mol
Last updated:2024-11-21 17:11:28

Torezolid Properties

Melting point 201 °C
Boiling point 614.5±65.0 °C(Predicted)
Density 1.57
storage temp. Refrigerator
solubility DMSO (Slightly, Heated), Water (Slightly, Heated)
form Solid
pka 14.05±0.10(Predicted)
color White to Off-White
InChI InChI=1S/C17H15FN6O3/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(9-25)27-17(24)26/h2-7,12,25H,8-9H2,1H3/t12-/m1/s1
InChIKey XFALPSLJIHVRKE-GFCCVEGCSA-N
SMILES O1[C@@H](CO)CN(C2=CC=C(C3=CC=C(C4=NN(C)N=N4)N=C3)C(F)=C2)C1=O
CAS DataBase Reference 856866-72-3
FDA UNII 97HLQ82NGL
ATC code J01XX11

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Warning
Hazard statements  H361-H373
Precautionary statements  P201-P202-P281-P308+P313-P405-P501-P260-P314-P501
HS Code  29339900

Torezolid price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TRC T013750 Tedizolid 856866-72-3 50mg $1190 2021-12-16 Buy
Matrix Scientific 153201 (R)-3-(3-Fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one 95% 856866-72-3 1g $1323 2021-12-16 Buy
Matrix Scientific 143684 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone 95% 856866-72-3 250mg $1832 2021-12-16 Buy
Matrix Scientific 143684 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone 95% 856866-72-3 100mg $916 2021-12-16 Buy
ChemScene CS-0687 Tedizolid 99.46% 856866-72-3 10mg $216 2021-12-16 Buy
Product number Packaging Price Buy
T013750 50mg $1190 Buy
153201 1g $1323 Buy
143684 250mg $1832 Buy
143684 100mg $916 Buy
CS-0687 10mg $216 Buy

Torezolid Chemical Properties,Uses,Production

Novel antibacterial drugs

Tedizolid belongs to the second generation oxazolidinone antibiotics, being an analog of linezolid as well as a kind of protein synthesis inhibitors, acting on the bacterial ribosomal 50S subunit and causing inhibition of bacterial protein synthesis. Compared with linezolid, the efficacy of the two is basically the same, but linezolid required to be taken for 2 times a day and for 10 continuous days while Tedizolid only takes 1 time daily and continuous taking for 6 days.
On June 20, 2014, the US FDA had approved a new antimicrobial drug Tedizolid (trade name: Sivextro) for the treatment of skin infections in adult patients. Sivextro is approved for the treatment of acute bacterial skin and skin infections caused by certain sensitive bacteria such as Staphylococcus aureus (including methicillin-resistant strains and methicillin-sensitive strains), various streptococci and Enterococcus faecalis (ABSSSI). Sivextro is administered intravenously and orally.
Tedizolid phosphate is a second-generation oxazolidinone antibiotic developed by Dong-A Pharmaceutical, licensed to Cubist Pharmaceuticals and Bayer for commercial development.
Sivextro is designed for the treatment of serious or life-threatening infections, and its listing applications are eligible for Qualified Infectious Disease Products (QIDP) and have obtained the approve of FDA for accelerated review. Sivextro's QIDP eligibility gives the drug exclusive five-year market exclusivity, in addition to its market exclusivity under the Food, Drug, and Cosmetic Act.
The safety and efficacy of Sivextro were evaluated in two clinical trials involving 1315 ABSSSI adult patients. Subjects were randomized to Sivextro or another antibiotic linezolid approved for the treatment of acute bacterial skin and skin structure infections (ABSSSI). The results showed that its clinical efficacy is equivalent to linezolid. However, it will cause less gastrointestinal adverse reactions and thrombocytopenia adverse reactions than linezolid. The incidence of drug resistance is also lower. Tedizolid has been shown to be more tolerant than vancomycin.
The most common side effects identified in clinical trials include nausea, headache, diarrhea, vomiting and dizziness. The safety and efficacy of Sivextro have not been evaluated in patients with reduced white blood cell levels (neutropenia), so alternative therapies should be considered for these patients. Sivextro is marketed by Cubist Pharmaceuticals, Inc., based in Lexington, Massachusetts.
Status of intellectual property: Compound patent ZL200480037612.2, protection period 2024.12.17 expires.
This information was edited by Xiao Nan from Chemicalbook (2015-08-14).

Indications

Tedizolid phosphate is an oxazolidinone compound used in the treatment of acute bacterial skin and skin structure infections caused by the following gram-positive bacteria-sensitive strains: Staphylococcus aureus (including Methicillin-resistant and methicillin-susceptible strains), pyogenic streptococci, Streptococcus lactis, Streptococcus angustifolia (including Angina, Streptococcus intermedius and Streptococcus constellation), and Enterococcus faecalis.

State of Intellectual Property

(A) Administrative protection, new drug protection and new drug monitoring period
On August 9, 2013, Bayer Pharmaceuticals has filed a new drug application with CFDA.
(B) Domestic patent
1. Patented compounds
East Asia Pharmaceutical has applied for the compound patent in China under the application number is ZL200480037612.2. The date of application is December 17, 2004; the protection period will expire at 2024.12.17. Three subsequent divisional applications were further filed with the application numbers being 201010508824.1 (preparation), 201110304983.4, 201210155386.4.
On October 9, 2009, the Teresius Therapeutics Company has applied for a preparation method patent with the patent number of 200980140144.4.
2. Crystal patent
On February 3, 2010, Teulius Therapeutics applied for a crystalline form patent of free acid with the application number of 201080014363.0. Form I of the disclosed free acid has the advantage that it is more stable than the disodium salt and has no moisture absorption.
3. Formulation Composition Patents
The above-mentioned patent 200480037612.2 and its divisional application patent have disclosed the Tedizolid powder, tablet, capsule and injection.
The above-mentioned patent 201080014363.0 have disclosed the prescription of Tedizolid tablets and freeze-dried preparations.

Uses

Tedizolid, known as TR-700, is an oral and i.v administered intracellular antibacterial drug.

Definition

ChEBI: A member of the class of pyridines that is pyridine which is substituted by a 2-methyl-2H-tetrazol-5-yl group at position 2 and by a 2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl group at position 5 It is used as its phosphate pro-drug used for the treatment of acute bacterial skin and skin structure infections caused by certain susceptible bacteria, including Staphylococcus aureus (including methicillin-resistant strains (MRSA) and meth cillin-susceptible strains), various Streptococcus species, and Enterococcus faecalis.

Biological Activity

tedizolid is an oxazolidinone antimicrobial agent with mic50 value of 0.5 μg/ml for mssa, mrsa, vr e. faecium and vr e. faecalis and 0.25 μg/ml for msse, mrse, pssp and prsp [1].the resistant gram-positive infection is a serious global health problem. for instant, the methicillin-resistant s. aureus (mrsa) has spread all over the world with rates ranging from 18 to 26 cases among 100,000 people. besides that, there come out a serious of resistant strains such as the linezolid-resistant s. aureus (lrsa) and the vancomycin-resistant s. aureus (vrsa). due to the unfavorable outcomes of the existed antibiotics, alternative treatments have been developed. tedizolid is a synthetic antibiotic that works based on the inhibition of protein synthesis. it binds to the 50s ribosome and inhibits the formation of the 70s complex [1].tedizolid showed potent bacteriostatic activity against many resistant gram-positive pathogens such as mssa, mrsa, s. pyogenes and s. pneumoniae. for the enterococcal and staphylococcal isolates, tedizolid displayed more than 4-fold higher potency than that of linezolid. it also showed inhibitory effects on a panel of 169 linezolid-resistant staphylococcal isolates with 79.2% inhibition at concentration of ≤ 4μg/ml. the mic values of tedizolid against linezolid-resistant staphylococci were in a range from 0.06 to 16 mg/l. besides that, tedizolid was found to be the inhibitors of human monoamine oxidase with ic50 values of 8.7 and 5.7 μm for mao-a and mao-b, respectively [1, 2 and 3].when treated in vivo, tedizolid was the active moiety converted from the pro-drug tedizolid phosphate. it was found that granulocytes could affect the antistaphylococcal effect of tedizolid. in neutropenic mice, the administration of tedizolid for 24 hours or 48 hours caused ed50 values of 25.2 and 35.7 mg/kg/day, respectively [1 and 4].

References

[1] kanafani z a, corey g r. tedizolid (tr-701): a new oxazolidinone with enhanced potency. expert opinion on investigational drugs, 2012, 21(4): 515-522.
[2] rodríguez-avial i, culebras e, betriu c, et al. in vitro activity of tedizolid (tr-700) against linezolid-resistant staphylococci. journal of antimicrobial chemotherapy, 2012, 67(1): 167-169.
[3] flanagan s, bartizal k, minassian s l, et al. in vitro, in vivo, and clinical studies of tedizolid to assess the potential for peripheral or central monoamine oxidase interactions. antimicrobial agents and chemotherapy, 2013, 57(7): 3060-3066.
[4] louie a, liu w, kulawy r, et al. in vivo pharmacodynamics of torezolid phosphate (tr-701), a new oxazolidinone antibiotic, against methicillin-susceptible and methicillin-resistant staphylococcus aureus strains in a mouse thigh infection model. antimicrobial agents and chemotherapy, 2011, 55(7): 3453-3460.

444335-16-4
380380-64-3
856866-72-3
Synthesis of Torezolid from (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE and 5-BROMO-2-(2-METHYL-2H-TETRAZOL-5-YL)-PYRIDINE
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View Lastest Price from Torezolid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone pictures 2024-12-19 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone
856866-72-3
 US $0.00-0.00 / g 100g 99 20kgs Cangzhou Kangrui Pharma Tech Co. Ltd.,
Torezolid pictures 2024-11-21 Torezolid
856866-72-3
 US $10.00 / KG 1KG 99% 10 mt Hebei Weibang Biotechnology Co., Ltd
Torezolid pictures 2024-11-01 Torezolid
856866-72-3
 US $0.00-0.00 / KG 1KG 99% 500KG Hangzhou Hyper Chemicals Limited
  • Torezolid pictures
  • Torezolid
    856866-72-3
  • US $10.00 / KG
  • 99%
  • Hebei Weibang Biotechnology Co., Ltd
  • Torezolid pictures
  • Torezolid
    856866-72-3
  • US $0.00-0.00 / KG
  • 99%
  • Hangzhou Hyper Chemicals Limited

Torezolid Spectrum

3- [3-fluoro-4- [6- (2-methyl--2H- tetrazol-5-yl) -3-pyridinyl] phenyl] -5- (hydroxymethyl) -2-oxazolidine ketone Tedizolid free base 3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one TEDIZOLID;TR-700; DA-7157 (R)-3-(3-Fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolid 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidi 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone DA 7157 DA-7157 Torezolid -3-(4-(2-(2-Methyltetrazol-5-yl)pyridine-5-yl)-3-fluorophenyl)-5-hydroxyMethyl oxazolidin-2-one Tedizolid (TR-701) Torezolid (TR-701 (5R)-3-{3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)pyridin-3-yl]phenyl}-5-(hydroxyMethyl)-1,3-oxazolidin-2-one Phosphate Specially acetazolaMide (R)-3-(4-(2-(2-Methyltetrazol-5-yl)pyridine-5-yl)-3-fluorophenyl)-5-hydroxyMethyl oxazolidin-2-one (5R)-3-[3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-Oxazolidin 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone Torezolid (TR-701 (5R)-3-[3-fluoro-4-[6-(2-methyltetrazol-5-yl)pyridin-3-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Tedizolid impurity580 Torezolid USP/EP/BP -3-(4-(2-(2-Methyltetrazol-5-yl)pyridine-5-yl)-3-fluorophenyl)-5-hydroxyMethyl oxazolidin-2-one phosphate 2-Oxazolidinone, 3-[3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-, (5R)- DA-7157，Torezolid,TR 700 Torezolid Related substance I Impurity 1.10 Tedizolid (TR 700 Torezolid856866-72-3 (R)-3-(3-fluoro-4-(6-(2-methyl-2H Torezolid-21 (R)-3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one，Torezolid Tedizolid (R)-3-(3-fluoro-4-(6-(2-Methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxyMethyl)oxazolidin-2-one Tedizolidted CS-1826 Tedizolid Impurity 47 Specially thiazole amine Benzenepropanoicacid,6-chloro-β-oxo-,ethylester (R)-3-(3-Fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one (Tedizolid Impurity) Terazolamide impurity 23 Tedizolid HCl(free base) (5R)-3-{3-Fluoro-4-[6-(2-Methyl-2H-Tetrazol-5-yl)-Pyridin-3-yl]-Phenyl}-5-Hydroxymethyl-Oxazolidin-2-One (R)-3-(3-fluoro-4-(6-(2-Methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-5- (hydroxyMethyl)oxazolidin-2-one, Free base 856866-72-3 856866-44-0 856866-72-7 C17H15FN6O3 Inhibitors Tedizolid intermediates 856866-72-3