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2D Structure
Also known as: 3424-98-4, 2'-deoxy-l-thymidine, Epavudine, L-thymidine, Beta-l-thymidine, Tyzeka
Molecular Formula
C10H14N2O5
Molecular Weight
242.23  g/mol
InChI Key
IQFYYKKMVGJFEH-CSMHCCOUSA-N
FDA UNII
2OC4HKD3SF

A thymidine derivative and antiviral agent that inhibits DNA synthesis by HEPATITIS B VIRUS and is used for the treatment of CHRONIC HEPATITIS B.
Telbivudine is a Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of telbivudine is as a Nucleoside Reverse Transcriptase Inhibitor.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
2.1.2 InChI
InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m1/s1
2.1.3 InChI Key
IQFYYKKMVGJFEH-CSMHCCOUSA-N
2.1.4 Canonical SMILES
CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
2.1.5 Isomeric SMILES
CC1=CN(C(=O)NC1=O)[C@@H]2C[C@H]([C@@H](O2)CO)O
2.2 Other Identifiers
2.2.1 UNII
2OC4HKD3SF
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(2-deoxy-beta-l-erythropentafuranosyl)-5-methyl-2,4(1h,3h)-pyrimidinedione

2. Beta L 2' Deoxythymidine

3. Beta-l-2'-deoxythymidine

4. Telbivudin

5. Tyzeka

2.3.2 Depositor-Supplied Synonyms

1. 3424-98-4

2. 2'-deoxy-l-thymidine

3. Epavudine

4. L-thymidine

5. Beta-l-thymidine

6. Tyzeka

7. L-dt

8. Telbivudin

9. Sebivo

10. L-deoxythymidine

11. Nv-02b

12. Ldt600

13. Beta-l-2'-deoxythymidine

14. 26879-47-0

15. Ldt

16. Nv 02b

17. Ldt-600

18. Chebi:63624

19. 1-(2-deoxy-beta-l-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1h,3h)-dione

20. 2oc4hkd3sf

21. 1-((2s,4r,5s)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione

22. 1-(2-deoxy-beta-l-ribofuranosyl)-5-methyluracil

23. Telbivudine [usan]

24. 1-[(2s,4r,5s)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

25. Mfcd02683612

26. Llt

27. Tyzeka (tn)

28. Unii-2oc4hkd3sf

29. Telbivudine (usan/inn)

30. Telbivudine [usan:inn:ban]

31. 1-[(2s,4r,5s)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

32. Telbivudine [mi]

33. B-l-2'-deoxy-thymidine

34. Telbivudine [inn]

35. Telbivudine [vandf]

36. Telbivudine [mart.]

37. Telbivudine [who-dd]

38. Schembl124279

39. Telbivudine (sebivo, Tyzeka)

40. Telbivudine [ema Epar]

41. Chembl374731

42. Epavudine;l-thymidine;nv 02b

43. Thymine, 1-(2-deoxy-beta-l-erythro-pentofuranosyl)-

44. Zinc2159

45. Telbivudine, >=98% (hplc)

46. Dtxsid30187813

47. Telbivudine [orange Book]

48. Amy23971

49. Hy-b0017

50. Bdbm50088372

51. S1651

52. Akos025117349

53. Ac-5632

54. Ccg-266887

55. Cs-1934

56. Db01265

57. 2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-b-l-erythro-pentofuranosyl)-5-methyl-

58. 2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-beta-l-erythro-pentofuranosyl)-5-methyl-

59. Ncgc00346560-01

60. Ncgc00346560-06

61. Ncgc00346560-12

62. 1-[(2s,4r,5s)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione

63. As-35209

64. Sw220236-1

65. D06675

66. Ab01274717-01

67. Ab01274717_02

68. Q413621

69. Brd-k15976406-001-01-7

70. Thymine, 1-(2-deoxy-.beta.-l-erythro-pentofuranosyl)-

71. Z2574360267

72. 1-[(2r,4r,5s)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

73. 1-[(2s,4r,5s)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione

74. 2,4(1h,3h)-pyrimidinedione,1-(2-deoxy-.beta.-l-erythro-pentofuranosyl)-5-methyl-

75. 1-((2s,4s,5s)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione

76. L-thymidine; Beta-l-thymidine; L-dt; 2'-deoxy-l-thymidine; 1-(2-deoxy-beta-l-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1h,3h)-dione

2.4 Create Date
2005-07-07
3 Chemical and Physical Properties
Molecular Weight 242.23 g/mol
Molecular Formula C10H14N2O5
XLogP3-1.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass242.09027155 g/mol
Monoisotopic Mass242.09027155 g/mol
Topological Polar Surface Area99.1 Ų
Heavy Atom Count17
Formal Charge0
Complexity381
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameTyzeka
PubMed HealthTelbivudine (By mouth)
Drug ClassesAntiviral
Drug LabelTyzeka is the trade name for telbivudine, a synthetic thymidine nucleoside analogue with activity against hepatitisB virus (HBV). The chemical name for telbivudine is 1-((2S,4R,5S)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-y1)-5-methyl-1H-pyrimidi...
Active IngredientTelbivudine
Dosage FormTablet
RouteOral
Strength600mg
Market StatusPrescription
CompanyNovartis

2 of 2  
Drug NameTyzeka
PubMed HealthTelbivudine (By mouth)
Drug ClassesAntiviral
Drug LabelTyzeka is the trade name for telbivudine, a synthetic thymidine nucleoside analogue with activity against hepatitisB virus (HBV). The chemical name for telbivudine is 1-((2S,4R,5S)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-y1)-5-methyl-1H-pyrimidi...
Active IngredientTelbivudine
Dosage FormTablet
RouteOral
Strength600mg
Market StatusPrescription
CompanyNovartis

4.2 Drug Indication

For the treatment of chronic hepatitis B in adult and adolescent patients 16 years of age with evidence of viral replication and either evidence of persistent elevations in serum aminotransferases (ALT or AST) or histologically active disease.


Sebivo is indicated for the treatment of chronic hepatitis B in adult patients with compensated liver disease and evidence of viral replication, persistently elevated serum alanine aminotransferase (ALT) levels and histological evidence of active inflammation and/or fibrosis.

Initiation of Sebivo treatment should only be considered when the use of an alternative antiviral agent with a higher genetic barrier to resistance is not available or appropriate.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Telbivudine is a synthetic thymidine nucleoside analogue with activity against hepatitis B virus (HBV). Telbivudine is the unmodified L enantiomer of the naturally occurring nucleoside, thymidine. It undergoes phosphorylation via interaction with cellular kinases to form the active metabolite, telbivudine 5'-triphosphate.


5.2 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


Nucleic Acid Synthesis Inhibitors

Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TELBIVUDINE
5.3.2 FDA UNII
2OC4HKD3SF
5.3.3 Pharmacological Classes
Mechanisms of Action [MoA] - Nucleoside Reverse Transcriptase Inhibitors
5.4 ATC Code

J05AF11


J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors

J05AF11 - Telbivudine


5.5 Absorption, Distribution and Excretion

Absorption

Absorbed following oral administration. Telbivudine absorption and exposure were unaffected when a single 600mg dose was administered with a highfat (~55 g), highcalorie (~950 kcal) meal.


Route of Elimination

Telbivudine is eliminated primarily by urinary excretion of unchanged drug.


Clearance

7.6 +/- 2.9 L/h [Normal renal function (Clcr>80 mL/min)]

5.0 +/- 1.2 L/h [Mild renal function impairement (Clcr=50-80 mL/min)]

2.6 +/- 1.2 L/h [Moderate renal function impairement (Clcr=30-49 mL/min)]

0.7 +/- 0.4 L/h [Severe renal function impairement (Clcr<30 mL/min)]


5.6 Metabolism/Metabolites

No metabolites of telbivudine were detected following administration of [14C]telbivudine in humans. Telbivudine is not a substrate, or inhibitor of the cytochrome P450 (CYP450) enzyme system.


5.7 Biological Half-Life

Approximately 15 hours.


5.8 Mechanism of Action

Telbivudine 5'triphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate, thymidine 5'triphosphate. This leads to the chain termination of DNA synthesis, thereby inhibiting viral replication. Incorporation of telbivudine 5'triphosphate into viral DNA also causes DNA chain termination, resulting in inhibition of HBV replication. Telbivudine inhibits anticompliment or second-strand DNA.