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
Structure for Telbivudine (DB01265)
- 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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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAdenovirus 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. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 Canada 
Sebivo Tablet, film coated 600 mg Oral Novartis Europharm Limited 2016-09-08 2021-01-14 EU 
Sebivo Tablet, film coated 600 mg Oral Novartis Europharm Limited 2016-09-08 2021-01-14 EU Sebivo Solution 20 mg/ml Oral Novartis Europharm Limited 2016-09-08 2021-01-14 EU Tyzeka Tablet, film coated 600 mg/1 Oral Novartis Pharmaceuticals Corporation 2006-11-06 2006-11-06 US 
Tyzeka Tablet, film coated 600 mg/1 Oral Novartis Pharmaceuticals Corporation 2006-10-25 2018-02-28 US Tyzeka Solution 20 mg/1mL Oral Novartis Pharmaceuticals Corporation 2009-04-28 2010-03-01 US
Categories
- ATC Codes
- J05AF11 — Telbivudine
- 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 show 5 more
- Substituents
- Alcohol / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound / Organic oxide / Organic oxygen compound 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
- 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]
- Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. [Article]
- Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. [Article]
- Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. [Article]
- 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]
- Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. [Article]
- 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]
- 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
- 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
- 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 Virus Infection / Viral sepsis 1 4 Completed Prevention Complications / Hepatitis B Chronic Infection / Pregnancy Late / 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 Elevations in serum alanine aminotransferase (ALT) / Hepatitis B Chronic Infection / High Viral Load / Pregnancy, Complications 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 Tablet, film coated Oral 600.0 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 Canada US6395716 No 2002-05-28 2019-08-10 US US6444652 No 2002-09-03 2019-08-10 US US6566344 No 2003-05-20 2019-08-10 US US6569837 No 2003-05-27 2020-10-25 US US7589079 No 2009-09-15 2023-09-11 US US7795238 No 2010-09-14 2019-08-10 US US7858594 No 2010-12-28 2023-09-11 US
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
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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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- 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]
- 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]
- Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. [Article]
- Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. [Article]
- 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]
- 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]
- Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. [Article]
Yes
References
- 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]
- 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]
- 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]
Drug created at May 16, 2007 17:51 / Updated at December 01, 2021 01:05