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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

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 Formula	C₁₇H₁₆FN₆O₆P
Molecular Weight	450.3 g/mol
XLogP3	0.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	6
Exact Mass	450.08529741 g/mol
Monoisotopic Mass	450.08529741 g/mol
Topological Polar Surface Area	153 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	702
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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 C_max 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 T_max 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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LGM Pharma

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About the Company : LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, ...

LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, analytical method development and testing, and commercial manufacturing. LGM Pharma offers custom API synthesis, analytical development, and regulatory services. With a network of over 300 accredited CGMP manufacturing partners, LGM provides unparalleled supply chain security. And, with over 100,000 square feet of FDA-inspected cGMP manufacturing and warehouse capacity, LGM Pharma provides a one-stop solution for solid dose, powder, semi-solid and liquid drugs.

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Metrochem API Private Limited

India

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Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product ...

Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product groups and has been approved by ISO 9001-2015, USFDA, WHO GMP, Cofepris & Japanese authorities. Metrochem’s in-depth industry knowledge, & hi-tech & advanced infrastructure, helps it provide quality products to its customers. Note: None of the products will be supplied to the countries where this could conflict with existing patents. Further, any products under patent will be offered for R&D purposes only. However, the final responsibility lies with the buyer