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    Chemistry

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    Also known as: 856867-55-5, Torezolid phosphate, Tr-701fa, Tr-701 fa, Tedizolid (phosphate), Tedizolid phosphate [usan]
    Molecular Formula
    C17H16FN6O6P
    Molecular Weight
    450.3  g/mol
    InChI Key
    QCGUSIANLFXSGE-GFCCVEGCSA-N
    FDA UNII
    O7DRJ6R4DW
    Tedizolid
    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.
    1 2D Structure

    Tedizolid

    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]-2-oxo-1,3-oxazolidin-5-yl]methyl dihydrogen phosphate
    2.1.2 InChI
    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
    2.1.3 InChI Key
    QCGUSIANLFXSGE-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)COP(=O)(O)O)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)COP(=O)(O)O)F
    2.2 Other Identifiers
    2.2.1 UNII
    O7DRJ6R4DW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Da 7218

    2. Da-7218

    3. Da7218

    4. Sivextro

    5. Torezolid Phosphate

    6. Tr 701

    7. Tr-701

    2.3.2 Depositor-Supplied Synonyms

    1. 856867-55-5

    2. Torezolid Phosphate

    3. Tr-701fa

    4. Tr-701 Fa

    5. Tedizolid (phosphate)

    6. Tedizolid Phosphate [usan]

    7. (r)-(3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl Dihydrogen Phosphate

    8. Chebi:83326

    9. Tr-701-fa

    10. O7drj6r4dw

    11. Tr-701

    12. 856867-55-5 (phosphate)

    13. [(5r)-3-[3-fluoro-4-[6-(2-methyltetrazol-5-yl)pyridin-3-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl Dihydrogen Phosphate

    14. Tedizolidphosphate

    15. [(5r)-3-{3-fluoro-4-[6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl Dihydrogen Phosphate

    16. Unii-o7drj6r4dw

    17. Tedizolid-phosphate

    18. Sivextro (tn)

    19. Da-7218 Free Acid

    20. Schembl1557561

    21. Chembl2105669

    22. Tedizolid Phosphate [mi]

    23. Tedizolid Phosphate (jan/usan)

    24. Amy9256

    25. Dtxsid30234977

    26. Tedizolid Phosphate [jan]

    27. Tedizolid Phosphate [vandf]

    28. Bcp10960

    29. Ex-a5792

    30. Tr-701 Free Acid Phosphate

    31. Bdbm50017198

    32. Da7218

    33. Hy-14855b

    34. Mfcd28098176

    35. S4641

    36. Tedizolid Phosphate [who-dd]

    37. Zinc43100953

    38. Akos027250820

    39. Ccg-269233

    40. Cs-5004

    41. Db09042

    42. Ncgc00482851-02

    43. Tedizolid Phosphate [orange Book]

    44. As-57141

    45. D09686

    46. Tr701-fa; Tr-701-fa; Tr 701-fa

    47. A863474

    48. Q21011227

    49. ((5r)-3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5- Yl)methyl Hydrogen Phosphate

    50. ((5r)-3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl Hydrogen Phosphate

    51. 2-oxazolidinone, 3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)-3-pyridinyl)phenyl)-5- ((phosphonooxy)methyl)-, (5r)-

    52. 2-oxazolidinone, 3-(3-fluoro-4-(6-(2-methyl-2h-tetrazol-5-yl)-3-pyridinyl)phenyl)-5-((phosphonooxy)methyl)-, (5r)-

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 450.3 g/mol
    Molecular Formula C17H16FN6O6P
    XLogP30.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count6
    Exact Mass450.08529741 g/mol
    Monoisotopic Mass450.08529741 g/mol
    Topological Polar Surface Area153 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity702
    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.

    FDA Label

    Sivextro is indicated for the treatment of acute bacterial skin and skin structure infections (ABSSSI) in adults and adolescents 12 years of age and older.

    Treatment of acute bacterial skin and skin structure infections

    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 Pharmacological Classes
    Oxazolidinone Antibacterial [EPC]; Oxazolidinones [CS]; Breast Cancer Resistance Protein Inhibitors [MoA]
    5.4 ATC Code

    J01XX11

    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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