Tedizolid

Structural formula
General
Non-proprietary name	Tedizolid
other names	(5 R ) -3- {3-fluoro-4- [6- (2-methyl-2 H -tetrazol-5-yl) pyridin-3-yl] phenyl} -5- (hydroxymethyl) -1,3- oxazolidin-2-one; ( R ) -3- {3-fluoro-4- [6- (2-methyl-2 H -tetrazol-5-yl) pyridin-3-yl] phenyl} -5- (hydroxymethyl) -1,3-oxazolidin -2-on; TR-700; Torezolid;
Molecular formula	C 17 H 15 FN 6 O 3
External identifiers / databases
ECHA InfoCard	100.249.430
PubChem	11234049
DrugBank	DB14569
Wikidata	Q7825683
Drug information
ATC code	J01 XX11
Drug class	Oxazolidinones
Mechanism of action	Inhibition of bacterial protein synthesis
properties
Molar mass	370.34 g · mol -1
solubility	slightly soluble in dimethyl sulfoxide (phosphate) * soluble in tetrahydrofuran, methanol and acetone (phosphate) * poorly soluble in ethanol (phosphate) * slightly soluble in water (phosphate);
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302-410
	P: 264-270-273-301 + 312-330-391-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tedizolid (trade name Sivextro ) is adjacent to linezolid a reserve antibiotic of the group of the oxazolidinone and is used to treat infections of the skin and the tissue beneath the skin by multidrug-resistant bacteria such as MRSA used. Compared to linezolid, it is four to sixteen times more effective against staphylococci and enterococci . The dose used is usually 200 mg / day. Tedizolid was developed to market maturity by Trius Therapeutics and was subsequently taken over by Cubist Pharmaceuticals. The antibiotic was approved by the European Commission in 2015 . The bioavailability of tedizolid is 91%. The biological half-life is 12 hours.

Mode of action

Tedizolid is released from tedizolid phosphate by plasma phosphatases. By binding to bacterial 50S ribosomes near the binding site for the 30S subunit, it prevents the formation of the 70S initiation complex and thus bacterial protein biosynthesis. The unusual mechanism of action of tedizolid and other oxazolidinones makes the development of cross-resistance with other antibiotics unlikely.

Extraction and presentation

Several syntheses of tedizolid phosphate are described in the literature.

Individual evidence

↑ ^a ^b ^c Committee for Medicinal Products for Human Use: Assessment report Sivextro, International non-proprietary name: tedizolid phosphate , Procedure No. EMEA / H / C / 002846/0000, January 22, 2015.
↑ Weon Bin Im, Sun Ho Choi, Ju-Young Park, Sung Hak Choi, John Finn, Sung-Hwa Yoon: Discovery of torezolid as a novel 5-hydroxymethyl-oxazolidinone antibacterial agent. In: European Journal of Medicinal Chemistry. 46, 2011, p. 1027, doi : 10.1016 / j.ejmech.2011.01.014 .
↑ ^a ^b Selleck: Tedizolid Phosphate , accessed on December 27, 2019.
↑ Tedizolid (Sivextro). In: ARZNEI-NEWS.de. Retrieved February 5, 2017 .
^ Zeina A. Kanafani, G. Ralph Corey: Tedizolid (TR-701): a new oxazolidinone with enhanced potency . In: Expert Opinion on Investigational Drugs . tape 21 , no. 4 , April 2012, p. 515-522 , doi : 10.1517 / 13543784.2012.660250 , PMID 22324973 .
^ Entry on tedizolid. In: Römpp Online . Georg Thieme Verlag, accessed on February 8, 2017.
↑ Patent US9328087 : Methods for preparing oxazolidinones and compositions containing them. Filed November 25, 2013 , published May 3, 2016 , applicant: Merck Sharp & Dohme Corp., inventor: Carrie A. Costello, Jacqueline A. Ware, Robert J. Duguid. ‌
↑ Patent US8604209 : Methods for preparing oxazolidinones and compositions containing them. Filed October 9, 2009 , published December 10, 2013 , Applicant: Trius Therapeutics, Inc., Inventors: Jacqueline A. Ware, Carrie A. Costello, Robert J. Duguid, Douglas Phillipson. ‌

[Committee_for_Medicinal_Products_for_Human_Use-1] Committee for Medicinal Products for Human Use: Assessment report Sivextro, International non-proprietary name: tedizolid phosphate , Procedure No. EMEA / H / C / 002846/0000, January 22, 2015.

[DOI10.1016/j.ejmech.2011.01.014-2] Weon Bin Im, Sun Ho Choi, Ju-Young Park, Sung Hak Choi, John Finn, Sung-Hwa Yoon: Discovery of torezolid as a novel 5-hydroxymethyl-oxazolidinone antibacterial agent. In: European Journal of Medicinal Chemistry. 46, 2011, p. 1027, doi : 10.1016 / j.ejmech.2011.01.014 .

[Selleck-3] Selleck: Tedizolid Phosphate , accessed on December 27, 2019.

[4] Tedizolid (Sivextro). In: ARZNEI-NEWS.de. Retrieved February 5, 2017 .

[5] Zeina A. Kanafani, G. Ralph Corey: Tedizolid (TR-701): a new oxazolidinone with enhanced potency . In: Expert Opinion on Investigational Drugs . tape 21 , no. 4 , April 2012, p. 515-522 , doi : 10.1517 / 13543784.2012.660250 , PMID 22324973 .

[RömppOnline-6] Entry on tedizolid. In: Römpp Online . Georg Thieme Verlag, accessed on February 8, 2017.

[7] Patent US9328087 : Methods for preparing oxazolidinones and compositions containing them. Filed November 25, 2013 , published May 3, 2016 , applicant: Merck Sharp & Dohme Corp., inventor: Carrie A. Costello, Jacqueline A. Ware, Robert J. Duguid. ‌

[8] Patent US8604209 : Methods for preparing oxazolidinones and compositions containing them. Filed October 9, 2009 , published December 10, 2013 , Applicant: Trius Therapeutics, Inc., Inventors: Jacqueline A. Ware, Carrie A. Costello, Robert J. Duguid, Douglas Phillipson. ‌