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

Similar Structures

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

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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

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Chronic hepatitis b		••••••••••••

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
ADNA	Not Available	Humans
AProtein P	Not Available	HBV-F

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.

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.

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
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
Sebivo	Solution	20 mg/ml	Oral	Novartis Europharm Limited	2016-09-08	2021-01-14
Sebivo	Tablet	600 mg	Oral	Novartis	2006-12-14	2020-04-21
Tyzeka	Tablet, film coated	600 mg/1	Oral	Novartis Pharmaceuticals Corporation	2006-10-25	2018-02-28

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
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

PDB Entries

3qeo

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Prevention	Chronic Hepatitis B Infection	1
4	Completed	Prevention	Chronic Hepatitis B Infection / Complications / Pregnancy Late / Transmission	1
4	Completed	Prevention	Chronic Infection / Hepatitis B Virus Infection / Viral sepsis	1
4	Completed	Prevention	HBV	1
4	Completed	Treatment	Chronic Hepatitis B Infection	8

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)
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	23.2 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	splash10-0006-9420000000-ebaddd47fbf973a127a1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0032-9400000000-50b49c62fd5b3e635e9e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0ukc-0970000000-64f2ff121c49344e6c01
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-053s-9100000000-ea604ff67cec7cb3e665
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-9600000000-963395937553c2145ab6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-5900000000-e6f0bdfe8c34585c5fde
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-7900000000-67dec2d0a453354ed865
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	159.1906703	predicted	DarkChem Lite v0.1.0
[M-H]-	161.4513703	predicted	DarkChem Lite v0.1.0
[M-H]-	159.4537703	predicted	DarkChem Lite v0.1.0
[M-H]-	158.50969	predicted	DeepCCS 1.0 (2019)
[M+H]+	160.4882703	predicted	DarkChem Lite v0.1.0
[M+H]+	164.8653703	predicted	DarkChem Lite v0.1.0
[M+H]+	159.6535703	predicted	DarkChem Lite v0.1.0
[M+H]+	160.90578	predicted	DeepCCS 1.0 (2019)
[M+Na]+	159.1829703	predicted	DarkChem Lite v0.1.0
[M+Na]+	160.8793703	predicted	DarkChem Lite v0.1.0
[M+Na]+	159.4876703	predicted	DarkChem Lite v0.1.0
[M+Na]+	166.86752	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Details1. 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

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]

Details2. 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

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]

Drug created at May 16, 2007 17:51 / Updated at April 19, 2024 20:55

Telbivudine

Identification

Structure for Telbivudine (DB01265)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References