(5R)-3-[3-fluoro-4-[6-(2-methyltetrazol-5-yl)pyridin-3-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one manufacturers and suppliers on PharmaCompass

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Also known as: Torezolid, 856866-72-3, Tr-700, Da-7157, Da 7157, Tr 700
Molecular Formula
C17H15FN6O3
Molecular Weight
370.3  g/mol
InChI Key
XFALPSLJIHVRKE-GFCCVEGCSA-N
FDA UNII
97HLQ82NGL

(5R)-3-[3-fluoro-4-[6-(2-methyltetrazol-5-yl)pyridin-3-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one
Drug-resistant bacteria, such as methicillin-resistant Staphylococcus aureus, vancomycin-resistant Enterococcus faecium, and penicillin-resistant Streptococcus penumoniae, represent a massive public health threat. Tedizolid is a member of the oxazolidinone class of antibiotics, which includes the previously approved [linezolid] and is generally effective against multidrug-resistant Gram-positive bacteria. Tedizolid is indicated for the treatment of acute bacterial skin and skin structure infections (ABSSSI) and is generally more effective and more tolerable than [linezolid]. Tedizolid was approved by the FDA on June 20, 2014, for sale by Cubist Pharmaceuticals as tedizolid phosphate (SIVEXTRO). This product is currently available as both an oral tablet and as a powder for intravenous injection.
Tedizolid is an Oxazolidinone Antibacterial. The mechanism of action of tedizolid is as a Breast Cancer Resistance Protein Inhibitor.
1 2D Structure

(5R)-3-[3-fluoro-4-[6-(2-methyltetrazol-5-yl)pyridin-3-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(5R)-3-[3-fluoro-4-[6-(2-methyltetrazol-5-yl)pyridin-3-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one
2.1.2 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
2.1.3 InChI Key
XFALPSLJIHVRKE-GFCCVEGCSA-N
2.1.4 Canonical SMILES
CN1N=C(N=N1)C2=NC=C(C=C2)C3=C(C=C(C=C3)N4CC(OC4=O)CO)F
2.1.5 Isomeric SMILES
CN1N=C(N=N1)C2=NC=C(C=C2)C3=C(C=C(C=C3)N4C[C@@H](OC4=O)CO)F
2.2 Other Identifiers
2.2.1 UNII
97HLQ82NGL
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one

2. 3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-hydroxymethyloxazolidin-2-one

3. Torezolid

4. Tr 700

5. Tr-700

2.3.2 Depositor-Supplied Synonyms

1. Torezolid

2. 856866-72-3

3. Tr-700

4. Da-7157

5. Da 7157

6. Tr 700

7. Chebi:82717

8. 97hlq82ngl

9. (5r)-3-[3-fluoro-4-[6-(2-methyltetrazol-5-yl)pyridin-3-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one

10. (r)-3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one

11. (5r)-3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one

12. (5r)-3-{3-fluoro-4-[6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazolidin-2-one

13. 2-oxazolidinone, 3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)-3-pyridinyl)phenyl)-5-(hydroxymethyl)-, (5r)-

14. Tedizolid [usan:inn]

15. Unii-97hlq82ngl

16. Previously Torezolid

17. Torezolid; Sivextro

18. Tedizolid [inn]

19. Tedizolid [mi]

20. Tedizolid (usan/inn)

21. Tedizolid [usan]

22. Tedizolid [vandf]

23. Tedizolid [who-dd]

24. Schembl440398

25. Chembl1257051

26. Gtpl10865

27. Dtxsid10234975

28. Tr700

29. 1431699-67-0

30. Bcp02830

31. Ex-a5826

32. Bdbm50491954

33. Mfcd19442562

34. S5278

35. Zinc43100956

36. Akos025401974

37. Ccg-268294

38. Cs-0687

39. Db14569

40. Ncgc00379072-02

41. (5r)-3-[3-fluoro-4-[6-(2-methyltetrazol-5-yl)-3-pyridyl]phenyl]-5-(hydroxymethyl)oxazolidin-2-one

42. Ac-27738

43. As-56108

44. Hy-14855

45. A14965

46. D09685

47. Q7825683

48. (5r)-3-{3-fluoro-4-[6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl]phenyl}-5-(hydroxymethyl)-2-oxazolidinone

49. (r)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxymethyl Oxazolidin-2-on

50. (r)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxymethyl Oxazolidin-2-one

51. 3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one

52. 3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-hydroxymethyloxazolidin-2-one

53. U7v

2.4 Create Date
2006-10-26
3 Chemical and Physical Properties
Molecular Weight 370.3 g/mol
Molecular Formula C17H15FN6O3
XLogP31.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass370.11896652 g/mol
Monoisotopic Mass370.11896652 g/mol
Topological Polar Surface Area106 Ų
Heavy Atom Count27
Formal Charge0
Complexity543
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Tedizolid is indicated for the treatment of acute bacterial infections of the skin and skin structure (ABSSSI). To prevent drug resistance, tedizolid should only be used for infections that are caused by susceptible bacteria.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Tedizolid is an oxazolidinone antibiotic that works by inhibiting protein synthesis by bacterial ribosomes. However, oxazolidinone antibiotics can also bind to human mitochondrial, but not cytoplasmic, ribosomes. Mitochondrial protein synthesis inhibition is associated with adverse patient effects such as neurological, hematological, and gastrointestinal toxicity, although tedizolid is tolerated better than the related [linezolid]. Alternative therapies should be considered when treating neutropenic patients with ABSSSI. _Clostridium difficile_-associated diarrhea has been reported in patients treated with tedizolid.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TEDIZOLID
5.3.2 FDA UNII
97HLQ82NGL
5.3.3 Pharmacological Classes
Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors
5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01X - Other antibacterials

J01XX - Other antibacterials

J01XX11 - Tedizolid


5.5 Absorption, Distribution and Excretion

Absorption

Tedizolid reaches peak plasma concentrations within three hours for oral administration and within one hour following intravenous administration; the absolute oral bioavailability is approximately 91%. Food has no effect on absorption. When given once daily, either orally or intravenously, tedizolid reaches steady-state concentrations in approximately three days. The Cmax for tedizolid after a single dose/at steady-state is 2.0 0.7/2.2 0.6 mcg/mL for oral administration, and 2.3 0.6/3.0 0.7 mcg/mL for intravenous administration, respectively. Similarly, the Tmax has a median (range) of 2.5 (1.0 - 8.0)/3.5 (1.0 - 6.0) hrs for the oral route and 1.1 (0.9 - 1.5)/1.2 (0.9 - 1.5) hrs when given intravenous. The AUC is 23.8 6.8/25.6 8.4 mcg\*hr/mL for oral and 26.6 5.2/29.2 6.2 mcg\*hr/mL for intravenous.


Route of Elimination

When given as a single oral dose, approximately 82% of tedizolid is excreted via the feces and 18% in urine. The majority is found as the inactive sulphate conjugate, with only 3% recovered unchanged. Over 85% of the elimination occurs within 96 hours.


Volume of Distribution

The volume of distribution for tedizolid following a single intravenous dose of 200 mg is between 67 and 80 L. In a study involving oral administration of 200 mg tedizolid to steady-state, the volume of distribution was 108 21 L, while a single 600 mg oral dose resulted in an apparent volume of distribution of 113.3 19.3 L. Tedizolid has been observed to penetrate the interstitial space of both adipose and skeletal muscle tissue and is also found in the epithelial lining fluid as well as in alveolar macrophages.


Clearance

Tedizolid has an apparent oral clearance of 6.9 1.7 L/hr for a single dose and 8.4 2.1 L/hr at steady-state. The systemic clearance is 6.4 1.2 L/hr for a single dose and 5.9 1.4 L/hr at steady-state.


5.6 Metabolism/Metabolites

Tedizolid is administered as a phosphate prodrug that is converted to tedizolid (the circulating active moiety). Prior to excretion, the majority of tedizolid is converted to an inactive sulphate conjugate in the liver, though this is unlikely to involve the action of cytochrome P450-family enzymes.


5.7 Biological Half-Life

Tedizolid has a half-life of approximately 12 hours.


5.8 Mechanism of Action

Despite renewed efforts to combat the spread of antimicrobial resistance, multidrug-resistant organisms, including gram-positive bacteria such as methicillin-resistant _Staphylococcus aureus_, remain a threat. Oxazolidinones represent a relatively new class of antibacterials inhibiting protein synthesis that is generally capable of overcoming resistance to other bacterial protein synthesis inhibitors. Protein synthesis involves the action of ribosomes, multi-subunit complexes composed of both protein and ribosomal RNA (rRNA) substituents. Translocation along the length of a messenger RNA and concomitant protein synthesis involves the action of the A, P, and E sites of the peptidyltransferase centre (PTC), which accepts charged aminoacyl-tRNAs and catalyzes the formation of peptide bonds between them. The bacterial 70S ribosome comprises a small (30S) and a large (50S) subunit. Early studies into the mechanism of action of oxazolidinone antibiotics suggested that they inhibit a step in the initiation of protein synthesis. However, this mechanism was inconsistent with mapped resistance mutations, and later studies involving cross-linking and direct structural determination of the binding site revealed that oxazolidinones, including both [linezolid] and tedizolid, bind in the A site of the PTC by interacting with the 23S rRNA component. The structural studies also revealed that oxazolidinone binding alters the conformation of a conserved nucleotide in the 23S rRNA (U2585 in _Escherichia coli_), which renders the PTC non-productive for peptide bond formation. Hence, tedizolid exerts its effect through inhibiting bacterial protein synthesis.


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