Telbivudine

Identification

Summary

Telbivudine is a thymidine nucleoside analog used for the treatment of chronic hepatitis B with clinical evidence of viral replication or persistent elevations in serum aminotransferases (ALT or AST).

Generic Name

Telbivudine

DrugBank Accession Number

DB01265

Background

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.

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Telbivudine (DB01265)

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Weight

Average: 242.2286
Monoisotopic: 242.090271568

Chemical Formula

C₁₀H₁₄N₂O₅

Synonyms

• 1-(2-deoxy-β-L-ribofuranosyl)-5-methyluracil
• 2'-Deoxy-L-thymidine
• Beta-l-thymidine
• Epavudine
• L-deoxythymidine
• L-DT
• L-thymidine
• LDT
• Telbivudin
• Telbivudina
• Telbivudine
• β-L-2'-deoxythymidine

External IDs

• LDT-600
• LDT600
• NV-02B

Pharmacology

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.

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Associated Conditions

• Hepatitis B Chronic Infection

Contraindications & Blackbox Warnings

Contraindications & Blackbox Warnings

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Pharmacodynamics

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.

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.

Target	Actions	Organism
AProtein P	Not Available	HBV-F
ADNA	Not Available	Humans

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.

Volume of distribution

Not Available

Protein binding

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

Metabolism

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.

Route of elimination

Telbivudine is eliminated primarily by urinary excretion of unchanged drug.

Half-life

Approximately 15 hours.

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)]

Adverse Effects

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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.

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Adenovirus type 7 vaccine live	The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Telbivudine.
Anthrax vaccine	The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Telbivudine.
Bacillus calmette-guerin substrain connaught live antigen	The therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Telbivudine.
Bacillus calmette-guerin substrain russian BCG-I live antigen	The therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Telbivudine.
Bacillus calmette-guerin substrain tice live antigen	The therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Telbivudine.
BCG vaccine	The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Telbivudine.
Ganciclovir	The risk or severity of cytopenia can be increased when Ganciclovir is combined with Telbivudine.
Human adenovirus e serotype 4 strain cl-68578 antigen	The therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Telbivudine.
Interferon alfa-2a	The risk or severity of adverse effects can be increased when Interferon alfa-2a is combined with Telbivudine.
Interferon alfa-2b	The risk or severity of adverse effects can be increased when Interferon alfa-2b is combined with Telbivudine.

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Food Interactions

• Take with or without food. The absorption is unaffected by food.

Products

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Sebivo	Tablet	600 mg	Oral	Novartis	2006-12-14	2020-04-21
Sebivo	Solution	20 mg/ml	Oral	Novartis Europharm Limited	2016-09-08	2021-01-14
Sebivo	Tablet, film coated	600 mg	Oral	Novartis Europharm Limited	2016-09-08	2021-01-14
Sebivo	Tablet, film coated	600 mg	Oral	Novartis Europharm Limited	2016-09-08	2021-01-14
Tyzeka	Solution	20 mg/1mL	Oral	Novartis Pharmaceuticals Corporation	2009-04-28	2010-03-01
Tyzeka	Tablet, film coated	600 mg/1	Oral	Novartis Pharmaceuticals Corporation	2006-11-06	2006-11-06
Tyzeka	Tablet, film coated	600 mg/1	Oral	Novartis Pharmaceuticals Corporation	2006-10-25	2018-02-28

Categories

ATC Codes

J05AF11 — Telbivudine

• J05AF — Nucleoside and nucleotide reverse transcriptase inhibitors
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Anti-Infective Agents
• Antiinfectives for Systemic Use
• Antiviral Agents
• Antivirals for Systemic Use
• Carbohydrates
• Deoxyribonucleosides
• Direct Acting Antivirals
• Enzyme Inhibitors
• Glycosides
• Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor
• Nucleic Acid Synthesis Inhibitors
• Nucleic Acids, Nucleotides, and Nucleosides
• Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
• Nucleoside Reverse Transcriptase Inhibitors
• Nucleosides
• Nucleosides and Nucleotides
• Pyrimidine Nucleosides
• Pyrimidines

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Pyrimidones / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Secondary alcohols / Lactams / Oxacyclic compounds / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives

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Substituents

Alcohol / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Primary alcohol / Pyrimidine / Pyrimidine 2'-deoxyribonucleoside / Pyrimidone / Secondary alcohol / Tetrahydrofuran / Urea / Vinylogous amide

show 13 more

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidine 2'-deoxyribonucleoside (CHEBI:63624)

Affected organisms

• Hepatitis B virus

Chemical Identifiers

UNII

2OC4HKD3SF

CAS number

3424-98-4

InChI Key

IQFYYKKMVGJFEH-CSMHCCOUSA-N

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

IUPAC Name

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

SMILES

CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)NC1=O

References

General References

1. Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. doi: 10.1016/j.clinthera.2007.12.032. [Article]
2. Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. [Article]
3. Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. [Article]
4. Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. [Article]
5. 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. [Article]
6. Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. [Article]
7. Han SH: Telbivudine: a new nucleoside analogue for the treatment of chronic hepatitis B. Expert Opin Investig Drugs. 2005 Apr;14(4):511-9. [Article]
8. Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. [Article]

External Links

Human Metabolome Database

HMDB0015394

KEGG Drug

D06675

PubChem Compound

159269

PubChem Substance

46508706

ChemSpider

140081

BindingDB

50088372

RxNav

474128

ChEBI

63624

ChEMBL

CHEMBL374731

ZINC

ZINC000000002159

Therapeutic Targets Database

DAP000698

PharmGKB

PA164760861

PDBe Ligand

LLT

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Telbivudine

AHFS Codes

• 08:18.32 — Nucleosides and Nucleotides

PDB Entries

3hp1 / 3qeo

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Hepatitis B Chronic Infection	1
4	Completed	Prevention	Chronic Infection / Hepatitis B Infection / Viral sepsis	1
4	Completed	Prevention	Complications / Hepatitis B Chronic Infection / Late Pregnancy / Transmission	1
4	Completed	Prevention	HBV	1
4	Completed	Prevention	Hepatitis B Chronic Infection	1
4	Completed	Treatment	Chronic Kidney Disease (CKD) / Hepatitis B Chronic Infection	1
4	Completed	Treatment	Compensated Chronic Hepatitis B	1
4	Completed	Treatment	Complications, Pregnancy / Elevations in serum alanine aminotransferase (ALT) / Hepatitis B Chronic Infection / High Viral Load	1
4	Completed	Treatment	Hepatitis B Chronic Infection	8
4	Terminated	Treatment	HBsAg-positive Renal Allograft Recipients	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• Idenix Pharmaceutical Inc.
• Novartis AG

Dosage Forms

Form	Route	Strength
Solution	Oral	20 mg/ml
Tablet	Oral	600 mg
Tablet, film coated	Oral
Tablet, film coated	Oral	600 mg
Tablet, coated	Oral	600 mg
Solution	Oral	20 mg/1mL
Tablet, film coated	Oral	600 mg/1

Prices

Unit description	Cost	Unit
Tyzeka 600 mg tablet	27.26USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
CA2340156	No	2007-10-23	2019-08-10
US6395716	No	2002-05-28	2019-08-10
US6444652	No	2002-09-03	2019-08-10
US6566344	No	2003-05-20	2019-08-10
US6569837	No	2003-05-27	2020-10-25
US7589079	No	2009-09-15	2023-09-11
US7795238	No	2010-09-14	2019-08-10
US7858594	No	2010-12-28	2023-09-11

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	Sparingly soluble in water (>20 mg/mL)	Not Available
logP	-1.4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	66.8 mg/mL	ALOGPS
logP	-1.3	ALOGPS
logP	-1.1	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.1 Å2	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.41 m3·mol-1	ChemAxon
Polarizability	23.25 Å3	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.971
Blood Brain Barrier	+	0.5902
Caco-2 permeable	-	0.8851
P-glycoprotein substrate	Non-substrate	0.6468
P-glycoprotein inhibitor I	Non-inhibitor	0.8872
P-glycoprotein inhibitor II	Non-inhibitor	0.9128
Renal organic cation transporter	Non-inhibitor	0.9072
CYP450 2C9 substrate	Non-substrate	0.6893
CYP450 2D6 substrate	Non-substrate	0.8834
CYP450 3A4 substrate	Non-substrate	0.5083
CYP450 1A2 substrate	Non-inhibitor	0.9529
CYP450 2C9 inhibitor	Non-inhibitor	0.9392
CYP450 2D6 inhibitor	Non-inhibitor	0.9491
CYP450 2C19 inhibitor	Non-inhibitor	0.9479
CYP450 3A4 inhibitor	Non-inhibitor	0.9308
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9415
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.7872
Biodegradation	Not ready biodegradable	0.5131
Rat acute toxicity	1.8754 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9358
hERG inhibition (predictor II)	Non-inhibitor	0.8734

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. Protein P

Kind

Protein

Organism

HBV-F

Pharmacological action

Yes

General Function

Rna-dna hybrid ribonuclease activity

Specific Function

Multifunctional enzyme that converts the viral RNA genome into dsDNA in viral cytoplasmic capsids. This enzyme displays a DNA polymerase activity that can copy either DNA or RNA templates, and a ri...

Gene Name

P

Uniprot ID

Q05486

Uniprot Name

Protein P

Molecular Weight

94257.43 Da

References

1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
3. Lui YY, Chan HL: Treatment of chronic hepatitis B: focus on telbivudine. Expert Rev Anti Infect Ther. 2009 Apr;7(3):259-68. doi: 10.1586/eri.09.6. [Article]
4. Nash K: Telbivudine in the treatment of chronic hepatitis B. Adv Ther. 2009 Feb;26(2):155-69. doi: 10.1007/s12325-009-0004-y. Epub 2009 Feb 18. [Article]
5. Lui YY, Chan HL: A review of telbivudine for the management of chronic hepatitis B virus infection. Expert Opin Drug Metab Toxicol. 2008 Oct;4(10):1351-61. doi: 10.1517/17425255.4.10.1351 . [Article]
6. Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. [Article]
7. Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. [Article]
8. 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. [Article]
9. Han SH: Telbivudine: a new nucleoside analogue for the treatment of chronic hepatitis B. Expert Opin Investig Drugs. 2005 Apr;14(4):511-9. [Article]
10. Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. [Article]

Details2. DNA

Kind

Nucleotide

Organism

Humans

Pharmacological action

Yes

DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

References

1. Nash K: Telbivudine in the treatment of chronic hepatitis B. Adv Ther. 2009 Feb;26(2):155-69. doi: 10.1007/s12325-009-0004-y. Epub 2009 Feb 18. [Article]
2. Gaeta GB, Stornaiuolo G: Therapy of chronic hepatitis B: focus on telbivudine. Dig Liver Dis. 2007 Nov;39 Suppl 3:S372-8. doi: 10.1016/S1590-8658(07)60017-6. [Article]
3. 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. [Article]

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Drug created on May 16, 2007 17:51 / Updated on June 18, 2021 14:15