CAS 3424-98-4|CAS 50-89-5|Telbivudine|telbivudine|Sebivo|Beta-l-thymidine|L-deoxythymidine|L-DT|2'-Deoxy-L-thymidine|Tyzeka|L-thymidine|Epavudine|LDT|1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-...

General Information

Structure

Molecular Formula

C₁₀H₁₄N₂O₅

Molecular Mass

242.22856

Exact Mass

242.09027156

Charge

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

InChIKey

IQFYYKKMVGJFEH-CSMHCCOUSA-N

Canonic Smiles

OC[C@@H]1O[C@@H](C[C@H]1O)n1cc(C)c(=O)[nH]c1=O

Isomeric Smiles

O1[C@H](n2cc(c(=O)[nH]c2=O)C)C[C@@H](O)[C@@H]1CO

Calculated Properties

JChem

LogD (pH = 7.4)

-1.12

LogD (pH = 5.5)

-1.12

Log P

-1.12

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.96

Polar Surface Area

99.10

Polarizability

23.07

Molar Refractivity

55.41

LOG S

-0.88

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

SebivoTyzeka

IUPAC Traditional name

telbivudine

Synonyms

Beta-l-thymidineTelbivudineL-deoxythymidineL-DT2'-Deoxy-L-thymidineL-thymidineLDTEpavudinetelbivudineTelbivudin1-(2-Deoxy-beta-D-ribofuranosyl)-5-methyluracilThymidineSebivoTyzekaL-ThyMidine2'-Deoxy-L-thymidineBeta-l-thymidine1-(2-deoxy-beta-L-ribofuranosyl)-5-methyluracilLDTL-DTEpavudinebeta-L-2'-deoxythymidineL-thymidinetelbivudineL-deoxythymidine

IUPAC name

1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

API Name

Telbivudine

International Nonproprietary Name (INN)

telbivudine

Names and Identifiers

Registration numbers

CAS Number

3424-98-450-89-5

PubChem SID

16096459646508706135611174

PubChem CID

MDL Number

DrugBank ID

Protein Data Bank

PubMed Citation Links

22257108215862342209303421147187214574392223325521703206216709222174852222174039210404102164281422132702

Reaxys Registry

BKMS React Database

CHEMBL

SureChEMBL Database

CHEBI ID

BRENDA Database

BRENDA Ligand Database

14484

Wikipedia Title

Telbivudine

CompTox Database

DTXSID30187813

MetaboLights Database

MTBLS1693MTBLS3950MTBLS2145

BindingDB Database

50088372

ACToR Database

3424-98-4

Drug Central Database

4,220

KEGG DRUG Database

D06675

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-1.4

Solubility

Sparingly soluble in water (>20 mg/mL)

Melting Point

186-188°C

Safety Information

Storage Condition

-20°C

Product Information

Salt Data

Free Base

Purity

97%

Properties

Related Proteins

PDB Bank

3HP1

3QEO

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S1651

Research Area: Infection
Biological Activity:
Telbivudine(Tyzeka, Sebivo) is an antiviral drug used in the treatment of hepatitis B infection. Clinical trials have shown it to be significantly more effective than lamivudine or adefovir, and less likely to cause resistance. Telbivudine is a synthetic thymidine nucleoside analogue; it is the L-isomer of thymidine. It is taken once daily. [1]

DrugBank

DB01265

Drug Groups

approved; investigational

Description

Telbivudine is a synthetic thymidine nucleoside analog with specific activity against the hepatitis B virus. Telbivudine is orally administered, with good tolerance, lack of toxicity and no dose-limiting side effects.

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.

Pharmacology

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

Toxicity

There is no information on intentional overdose of telbivudine, but one subject experienced an unintentional and asymptomatic overdose. Healthy subjects who received telbivudine doses up to 1800 mg/day for 4 days had no increase in or unexpected adverse events. A maximum tolerated dose for telbivudine has not been determined.

Affected Organisms

Hepatitis B virus

Biotransformation

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.

Absorption

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

Half Life

Approximately 15 hours.

Protein Binding

In vitro binding of telbivudine to human plasma proteins is low (3.3%).

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)]

References

• Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. [Pubmed]

• Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. [Pubmed]

• Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. [Pubmed]

• Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. [Pubmed]

• Ruiz-Sancho A, Sheldon J, Soriano V: Telbivudine: a new option for the treatment of chronic hepatitis B. Expert Opin Biol Ther. 2007 May;7(5):751-61. [Pubmed]

• Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. [Pubmed]

• Han SH: Telbivudine: a new nucleoside analogue for the treatment of chronic hepatitis B. Expert Opin Investig Drugs. 2005 Apr;14(4):511-9. [Pubmed]

• Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. [Pubmed]

External Links

• [RxList]

• [Drugs.com]

ChEBI

CHEBI:63624

A pyrimidine 2'-deoxyribonucleoside that is the L-enantiomer of thymine. A synthetic thymidine nucleoside analogue with activity against HBV DNA polymerase.

Molecule Details

References

PubChem Literature

From Data Sources

• Ruiz-Sancho A, Sheldon J, Soriano V: Telbivudine: a new option for the treatment of chronic hepatitis B. Expert Opin Biol Ther. 2007 May;7(5):751-61. Pubmed

• Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. Pubmed

• Han SH: Telbivudine: a new nucleoside analogue for the treatment of chronic hepatitis B. Expert Opin Investig Drugs. 2005 Apr;14(4):511-9. Pubmed

• Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. Pubmed

• Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. Pubmed

• Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. Pubmed

• Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. Pubmed

• Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. Pubmed

• http://en.wikipedia.org/wiki/Telbivudine

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

Data Source

• Academic Data

• Commercial Catalog

Names and Identifiers

• Brand Name

• IUPAC Traditional name

• Synonyms

• IUPAC name

• API Name

• International Nonproprietary Name (INN)

Names and Identifiers

Registration numbers

• CAS Number

• PubChem SID

• PubChem CID

• MDL Number

• DrugBank ID

• Protein Data Bank

• PubMed Citation Links

• Reaxys Registry

• BKMS React Database

• CHEMBL

• SureChEMBL Database

• CHEBI ID

• BRENDA Database

• BRENDA Ligand Database

• Wikipedia Title

• CompTox Database

• MetaboLights Database

• BindingDB Database

• ACToR Database

• Drug Central Database

• KEGG DRUG Database

Registration numbers

Properties

• Physical Property

• Safety Information

• Product Information

Related Proteins

• PDB Bank

Molecular Spectra

Molecule Details

• Selleck Chemicals

• DrugBank

• ChEBI

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Brand Name

SebivoTyzeka

IUPAC Traditional name

telbivudine

Synonyms

IUPAC name

1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

API Name

Telbivudine

International Nonproprietary Name (INN)

telbivudine

CAS Number

MDL Number

Protein Data Bank

Reaxys Registry

BKMS React Database

SureChEMBL Database

CHEBI ID

BRENDA Database

BRENDA Ligand Database

14484

Wikipedia Title

Telbivudine

CompTox Database

DTXSID30187813

MetaboLights Database

MTBLS1693MTBLS3950MTBLS2145

BindingDB Database

50088372

ACToR Database

3424-98-4

Drug Central Database

4,220

KEGG DRUG Database

D06675

Physical Property

Hydrophobicity(logP)

-1.4

Solubility

Sparingly soluble in water (>20 mg/mL)

Melting Point

186-188°C

Safety Information

Storage Condition

-20°C

Product Information

Salt Data

Free Base

Purity

97%

Selleck Chemicals

S1651

DrugBank

DB01265

Drug Groups

approved; investigational

Description

Indication

Pharmacology

Toxicity

Affected Organisms

Hepatitis B virus

Biotransformation

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.

Absorption

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

Half Life

Approximately 15 hours.

Protein Binding

In vitro binding of telbivudine to human plasma proteins is low (3.3%).

Elimination

Telbivudine is eliminated primarily by urinary excretion of unchanged drug.

Clearance

References

• Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. [Pubmed]

• Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. [Pubmed]

• Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. [Pubmed]

• Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. [Pubmed]

• Ruiz-Sancho A, Sheldon J, Soriano V: Telbivudine: a new option for the treatment of chronic hepatitis B. Expert Opin Biol Ther. 2007 May;7(5):751-61. [Pubmed]

• Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. [Pubmed]

• Han SH: Telbivudine: a new nucleoside analogue for the treatment of chronic hepatitis B. Expert Opin Investig Drugs. 2005 Apr;14(4):511-9. [Pubmed]

• Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. [Pubmed]

External Links

• [RxList]

• [Drugs.com]

ChEBI

CHEBI:63624

A pyrimidine 2'-deoxyribonucleoside that is the L-enantiomer of thymine. A synthetic thymidine nucleoside analogue with activity against HBV DNA polymerase.

From Data Sources

• Ruiz-Sancho A, Sheldon J, Soriano V: Telbivudine: a new option for the treatment of chronic hepatitis B. Expert Opin Biol Ther. 2007 May;7(5):751-61. Pubmed

• Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. Pubmed

• Han SH: Telbivudine: a new nucleoside analogue for the treatment of chronic hepatitis B. Expert Opin Investig Drugs. 2005 Apr;14(4):511-9. Pubmed

• Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. Pubmed

• Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. Pubmed

• Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. Pubmed

• Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. Pubmed

• Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. Pubmed

• http://en.wikipedia.org/wiki/Telbivudine

Molecule

ID:1133