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Version 2.5
Creation Date 2007-05-16 17:51:54
Update Date 2009-02-19 16:04:49
Primary Accession Number DB01265
Secondary Accession Number Not Available
Name Telbivudine
Drug Type
  • Approved
  • Investigational
  • Small Molecule
Description Telbivudine is a drug with specific activity against the hepatitis B virus. Telbivudine is orally administered, with good tolerance, lack of toxicity and no dose-limiting side effects.
Synonyms
  1. 2'-Deoxy-L-thymidine
  2. Beta-l-thymidine
  3. Epavudine
  4. L-DT
  5. L-deoxythymidine
  6. L-thymidine
  7. LDT
  8. Telbivudin
  9. telbivudine
Brand Names
  1. Sebivo
  2. Tyzeka
Brand Mixtures Not Available
Chemical IUPAC Name 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
Chemical Formula C10H14N2O5
Chemical Structure Structure
CAS Registry Number 3424-98-4
InChI Identifier InChI=1/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/f/h11H
InChI Key IQFYYKKMVGJFEH-DWPOBJFODW
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 159269 Link Image
PubChem Substance 15220961 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02288389 Link Image
RxList Link http://www.rxlist.com/cgi/generic/tyzeka.htm Link Image
PDRhealth Link Not Available
Wikipedia Link Not Available
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 242.2286
Monoisotopic Molecular Weight 242.0903
State Solid
Melting Point Not Available
Experimental Water Solubility Sparingly soluble in water (>20 mg/mL) Source: PhysProp
Predicted Water Solubility 6.68e+01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -1.4 Source: PhysProp
Predicted LogP -1.31 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -0.56 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)NC1=O
Canonical SMILES CC1=CN(C2CC(O)C(CO)O2)C(=O)NC1=O
Drug Category
  • Antiviral Agents
  • Reverse Transcriptase Inhibitors
ATC Codes
AHFS Codes
  • 08:18.08.20
Indication For the treatment of chronic hepatitis B in adult patients 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.
Mechanism of Action Telbivudine 5'–triphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate, thymidine 5'–triphosphate. Incorporation of telbivudine 5'–triphosphate into viral DNA causes DNA chain termination, resulting in inhibition of HBV replication.
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.
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.
Protein Binding In vitro binding of telbivudine to human plasma proteins is low (3.3%).
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.
Half Life Approximately 15 hours.
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Peginterferon alfa-2a Co-administration of Peginterferon alpha-2a and Telbivudine may increase the risk of serious peripheral neuropathy.
Food Interactions
  • Take without regard to meals.
Pathways Not Available
General References
  1. RxList Link Image
Organisms Affected
  • Hepatitis B virus
Targets
  1. P protein [Includes: DNA-directed DNA polymerase
Drug Target 1 [top]
Target 1 ID 612
Target 1 Name P protein [Includes: DNA-directed DNA polymerase
Target 1 Synonyms
  1. EC 3.1.26.4]
  2. RNA- directed DNA polymerase
  3. Ribonuclease H
Target 1 Gene Name P
Target 1 Protein Sequence >P protein [Includes: DNA-directed DNA polymerase 
MPLSYPHFRKLLLLDDEAGPLEEELPRLADEDLNRRVAADLNLQLPNVSIPWTHKVGNFT
GLYSSTVPAFNPNWSTPSFPDIHLHQDLISKCEQFVGPLTKNELRRLKLVMPARFYPKVT
KYFPMDKGIKPYYPEHAVNHYFKTRHYLHTLWKAGILYKRESTRSASFCGSPYSWEQELQ
HGSTSLNDTKRHGTESLCAQSSGILSRPSAGSAIQSKFQQSRLGLQHKQGQLANGKQGRS
GRLRSRVHTPTRWPAGVEPSSTRCVNNLASRSASCFHQSAVREKANPSLSTSKRHTSTGN
AVELNPVPPSSVGSQGKGSVLPCWWLQFRDTEPCSDYCLSHIINLLEDWGPCYEHGQHYI
RTPRTPARVTGGVFLVDKNPHNTTESRLVVDFSQFSRGTTRVSWPKFAVPNLQSLTNLLS
SNLSWLSLDVSAAFYHLPLHPAAMPHLLVGSSGLSRYVARLSSTSRIHDHQHGTLQNLHN
SCTRNLYVSLLLLFQTLGRKLHLYSHPIILGFRKIPMGVGLSPFLLAQFTSAICSVVRRA
FPHCLAFSYMDDLVLGAKSVQHLESLYTAVTNFLLSVGIHLNTSKTKRWGYSLHFMGYVI
GSWGSLPQDHIVHKIKECFRKLPVNRPIDWKVCQRIVGLLGFAAPFTQCGYPALMPLYAC
ITAKQAFVFSPTYKAFLCKQYMNLYPVARQRPGLCQVFADATPTGWGLAIGHQRMRGTFV
APLPIHTAELLAACFARSRSGATLIGTDNSVVLSRKYTSFPWLLGCAANWILRGTSFVYV
PSALNPADDPSRGRLGLYRPLLRLPFQPTTGRTSLYADSPSVPSHLPDRVHFASPLHVAW
RPP
Target 1 Number of Residues 857
Target 1 Molecular Weight 94259
Target 1 Theoretical pI 10.12
Target 1 GO Classification
Function
RNA-directed DNA polymerase activity
RNA binding
transferase activity
transferase activity, transferring phosphorus-containing groups
nucleotidyltransferase activity
DNA-directed DNA polymerase activity
binding
nucleic acid binding
DNA binding
catalytic activity
hydrolase activity
hydrolase activity, acting on ester bonds
nuclease activity
endonuclease activity
endoribonuclease activity
endoribonuclease activity, producing 5'-phosphomonoesters
ribonuclease H activity
Process
RNA-dependent DNA replication
physiological process
metabolism
cellular metabolism
nucleobase, nucleoside, nucleotide and nucleic acid metabolism
DNA metabolism
DNA replication
Component
Not Available
Target 1 General Function Involved in RNA binding
Target 1 Specific Function Not Available
Target 1 Pathways
Name SMPDB Link KEGG Link
DNA polymerase map03030 Link Image
Purine metabolism SMP00050 Link Image map00230 Link Image
Pyrimidine metabolism SMP00046 Link Image map00240 Link Image
Target 1 Reactions
  • deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 59427 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q05486 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name DPOL_HBVA4 Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Cytoplasmic
Target 1 Gene Sequence >2532 bp 
ATGCCCCTATCCTATCCACACTTCCGGAAACTACTGTTGTTAGACGACGAGGCAGGTCCC
CTAGAAGAAGAACTCCCTCGCCTCGCAGACGAAGATCTCAATCGCCGCGTCGCCGCAGAT
CTCAATCTCCAGCTTCCCAATGTTAGTATTCCTTGGACTCATAAGGTGGGAAACTTTACG
GGGCTTTACTCTTCTACTGTGCCTGCTTTTAATCCTAACTGGTCCACTCCTTCTTTTCCT
GATATTCATTTGCATCAAGACCTGATTTCTAAATGTGAACAATTTGTAGGCCCACTTACT
AAAAATGAATTACGAAGATTAAAATTGGTTATGCCAGCTAGATTTTATCCTAAGGTTACC
AAATATTTTCCCATGGATAAAGGCATCAAACCCTATTATCCTGAGCATGCAGTTAATCAT
TACTTTAAAACCAGACATTATTTGCATACTTTATGGAAGGCGGGAATTTTATATAAGAGA
GAATCCACACGTAGCGCCTCATTTTGTGGGTCACCATATTCCTGGGAACAAGAGCTACAG
CATGGGAGCACCTCTCTCAACGACACGAAGAGGCATGGGACAGAATCTCTCTGTGCCCAA
TCCTCTGGGATTCTTTCCAGACCATCAGCTGGATCCGCTATTCAGAGCAAATTCCAGCAG
TCCCGACTGGGACTTCAACACAAACAAGGACAGTTGGCCAATGGCAAACAAGGTAGGAGT
GGGAGGCTACGGTCCAGGGTTCACACCCCCACACGGTGGCCTGCTGGGGTGGAGCCCTCA
AGCACAAGGTGTGTTAACAACCTTGCCAGCAGATCCGCCTCCTGCTTCCACCAATCGGCG
GTCCGGGAGAAAGCCAACCCCAGTCTCTCCACCTCTAAGAGACACACATCCACAGGCAAT
GCAGTGGAACTCAACCCAGTTCCACCAAGCTCTGTTGGATCCCAGGGTAAGGGCTCTGTA
CTTCCCTGCTGGTGGCTCCAGTTCAGGGACACAGAACCCTGCTCCGACTATTGCCTCTCT
CACATCATCAATCTTCTCGAAGACTGGGGGCCCTGCTATGAACATGGACAACATTACATC
AGGACTCCTAGGACCCCTGCTCGTGTTACAGGCGGTGTGTTTCTTGTTGACAAAAATCCT
CACAATACCACAGAGTCTAGACTCGTGGTGGACTTCTCTCAATTTTCTAGGGGGACTACC
CGGGTGTCCTGGCCAAAATTCGCAGTCCCCAACCTCCAATCACTTACCAACCTCCTGTCC
TCCAACTTGTCCTGGCTATCGTTGGATGTGTCTGCGGCGTTTTATCATCTTCCTCTTCAT
CCTGCTGCTATGCCTCATCTTCTTGTTGGTTCTTCTGGACTATCAAGGTATGTTGCCCGT
TTGTCCTCTACTTCCAGGATCCACGACCACCAGCACGGGACCCTGCAAAACCTGCACAAC
TCTTGCACAAGGAACCTCTATGTTTCCCTCCTGTTGCTGTTCCAAACCCTCGGACGGAAA
CTGCACTTGTATTCCCATCCCATCATCCTGGGCTTTAGGAAAATACCTATGGGAGTGGGC
CTCAGCCCGTTTCTCCTGGCTCAGTTTACTAGTGCAATTTGTTCAGTGGTGCGTCGGGCT
TTCCCCCACTGTTTGGCTTTTAGTTATATGGATGATCTGGTATTGGGGGCCAAATCTGTG
CAGCATCTTGAGTCCCTTTATACCGCTGTTACCAATTTTCTGTTATCTGTGGGTATCCAT
TTAAATACCTCTAAAACAAAAAGATGGGGTTACTCCCTACATTTTATGGGTTATGTCATT
GGTAGTTGGGGATCATTACCCCAAGATCACATTGTACACAAAATCAAGGAATGCTTTCGA
AAACTGCCTGTAAATCGTCCAATTGATTGGAAAGTTTGTCAACGCATAGTGGGTCTTTTG
GGCTTTGCTGCCCCTTTCACCCAATGCGGTTATCCTGCTCTCATGCCTCTGTATGCCTGT
ATTACTGCTAAACAGGCTTTTGTCTTCTCGCCAACCTACAAGGCCTTTCTGTGTAAACAA
TACATGAACCTTTACCCGGTTGCTCGGCAACGGCCAGGCCTGTGCCAAGTGTTTGCTGAC
GCAACCCCCACTGGTTGGGGCTTGGCCATTGGCCATCAGCGCATGCGTGGAACCTTTGTG
GCTCCTCTGCCGATCCATACTGCGGAACTCCTAGCAGCTTGTTTCGCTCGCAGCAGGTCT
GGAGCGACTCTCATCGGCACGGACAATTCTGTTGTCCTCTCTAGGAAGTACACCTCCTTT
CCATGGCTGCTCGGATGTGCTGCAAACTGGATCCTGCGCGGGACGTCCTTTGTTTACGTC
CCATCGGCGCTGAATCCCGCGGACGACCCCTCCCGGGGCCGCTTGGGGCTGTACCGCCCT
CTTCTCCGTCTGCCGTTCCAGCCGACGACGGGTCGCACCTCTCTTTACGCGGACTCCCCG
TCTGTTCCTTCTCATCTGCCGGACCGTGTGCACTTCGCTTCACCTCTGCACGTCGCATGG
AGACCACCGTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Naumann H, Schaefer S, Yoshida CF, Gaspar AM, Repp R, Gerlich WH: Identification of a new hepatitis B virus (HBV) genotype from Brazil that expresses HBV surface antigen subtype adw4. J Gen Virol. 1993 Aug;74 ( Pt 8):1627-32. [PubMed Link Image]
Target 1 Drug References
  1. 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. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

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