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Showing drug card for Entecavir (DB00442)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:43
Primary Accession Number DB00442
Secondary Accession Number
  • APRD00948
Name Entecavir
Drug Type
  • Approved
  • Investigational
  • Small Molecule
Description Entecavir is an oral antiviral drug used in the treatment of hepatitis B infection. It is marketed under the trade name Baraclude (BMS). Entecavir is a guanine analogue that inhibits all three steps in the viral replication process, and the manufacturer claims that it is more efficacious than previous agents used to treat hepatitis B (lamivudine and adefovir). It was approved by the U.S. Food and Drug Administration (FDA) in March 2005.
Synonyms
  1. entecavir
Brand Names
  1. Baraclude
Brand Mixtures Not Available
Chemical IUPAC Name 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one
Chemical Formula C12H15N5O3
Chemical Structure Structure
CAS Registry Number 142217-69-4
InChI Identifier InChI=1/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m0/s1/f/h15H,13H2
InChI Key QDGZDCVAUDNJFG-FUKFXOMTDO
KEGG Drug D04008 Link Image
KEGG Compound Not Available
PubChem Compound 153941 Link Image
PubChem Substance 641041 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02282224 Link Image
RxList Link http://www.rxlist.com/cgi/generic4/baraclude.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Entecavir Link Image
FDA Label
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 277.2792
Monoisotopic Molecular Weight 277.1175
State Solid
Melting Point Not Available
Experimental Water Solubility Slightly soluble (2.4 mg/mL at pH 7.9, 25oC) Source: PhysProp
Predicted Water Solubility 6.59e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -0.8 Source: PhysProp
Predicted LogP -0.80 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -1.62 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 NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](CO)C1=C
Canonical SMILES NC1=NC(=O)C2=C(N1)N(C=N2)C1CC(O)C(CO)C1=C
Drug Category
  • Antiviral Agents
ATC Codes
AHFS Codes
  • 08:18.32
Indication For the treatment of chronic hepatitis B virus infection in adults with evidence of active viral replication and either evidence of persistent elevations in serum aminotransferases (ALT or AST) or histologically active disease.
Pharmacology Entecavir is a guanosine nucleoside analogue with selective activity against hepatitis B virus (HBV). It is designed to selectively inhibit the Hepatitis B virus, blocking all three steps in the replication process. Entecavir is more efficient than an older Hepatitis B drug, lamivudine.
Mechanism of Action By competing with the natural substrate deoxyguanosine triphosphate, entecavir functionally inhibits all three activities of the HBV polymerase (reverse transcriptase, rt): (1) base priming, (2) reverse transcription of the negative strand from the pregenomic messenger RNA, and (3) synthesis of the positive strand of HBV DNA.
Absorption Absorption Following oral administration in healthy subjects, entecavir peak plasma concentrations occurred between 0.5 and 1.5 hours. In healthy subjects, the bioavailability of the tablet is 100% relative to the oral solution.
Toxicity Healthy subjects who received single entecavir doses up to 40 mg or multiple doses up to 20 mg/day for up to 14 days had no increase in or unexpected adverse events. If overdose occurs, the patient must be monitored for evidence of toxicity, and standard supportive treatment applied as necessary.
Protein Binding Binding of entecavir to human serum proteins in vitro is approximately 13%.
Biotransformation Entecavir is not a substrate, inhibitor, or inducer of the cytochrome P450 (CYP450) enzyme system. Entecavir is efficiently phosphorylated to the active triphosphate form.
Half Life After reaching peak concentration, entecavir plasma concentrations decreased in a bi-exponential manner with a terminal elimination half-life of approximately 128-149 hours. The phosphorylated metabolite has a half-life of 15 hours.
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions
  • Take on an empty stomach.
  • Taking the product with a high-fat meal or a light snack reduces the maximal concentration by 44 to 46% and total exposure by 18 to 20%.
Pathways Not Available
General References
  1. Wikipedia Link Image
  2. RxList Link Image
Organisms Affected
  • Hepatitis B virus
Targets
  1. P protein [Includes: DNA-directed DNA polymerase
Drug Target 1 [top]
Target 1 ID 342
Target 1 Name P protein [Includes: DNA-directed DNA polymerase
Target 1 Synonyms Not Available
Target 1 Gene Name P
Target 1 Protein Sequence >P protein [Includes: DNA-directed DNA polymerase 
MPLSYQHFRRLLLLDDEAGPLEEELPRLADEGLNRHVAEELNLGNLNVSIPWTHKVGNFT
GLYSSTVPVFNPHWKTPSFPNIHLHQDIIKKCEQFVGPLTVNEKRRLQLIMPARFYPKVT
KYLPLDKGIKPYYPEHLVNHYFQTRHYLHTLWKAGVLYKRETTHSASFCGSPYSWEQELQ
HGAESFHQQSSGILSRPPVGSSLQSKHCKSRLGLQSQQGLLARRQQGRSWSIRAGIHPTA
RRPFGVEPSGSGHTTNLASKSASCLHQSPVRKATYPSVSTFEKHSSSGHAVELHNLPPNS
ARSQSERPVSPCWWLQFRNSKPCSDYCLSHIVNLLEDWGPCAEHGEHHIRIPRTPARVTG
GVFLVDKNPHNTEESRLVVDFSQFSRGNHRVSWPKFAVPNLQSLTNLLSSNLSWLSLDVS
AAFYHLPLHPAAMPHLLVGSSGLSRYVARLSSDSRIFNHQHGTMQNLHDSCSRNLYVSLL
LLYQTFGRKLHLYSHPIILGFRKIPMGVGLSPFLLAQFTSAICSVVRRAFPHCLAFSYMD
DVVLGAKTVHHLESLFTAVTNFLLSLGIHLNPNKTKRWGYSLHFMGYVIGCYGSLPQDHI
IQKIKECFRKLPVNRPIDWKVCQRIVGLLGFAAPFTQCGYPALMPLYACIQSKQAFTFSP
TYKAFLCKQYLNLYPVARQRPGLCQVFADATPTGWGLVMGHQRMRGTFQAPLPIHTAELL
AACFARSRSGANILGTDNSVVLSRKYTSFPWLLGCAANWILRGTSFVYVPSALNPADDPS
RGRLGLSRPLLRLPFRPTTGRTSLYADSPSVPSHLPDRVHFASPLHVAWRPP
Target 1 Number of Residues 845
Target 1 Molecular Weight 93591
Target 1 Theoretical pI 10.05
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 329670 Link Image
Target 1 UniProtKB/Swiss-Prot ID P24024 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name DPOL_HBVIA Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Cytoplasmic
Target 1 Gene Sequence >2499 bp 
ATGCCCCTATCTTATCAACACTTCCGGAGACTACTGTTGTTAGACGACGAGGCAGGTCCC
CTAGAAGAAGAACTCCCTCGCCTCGCAGACGAAGGTCTCAATCGCCACGTCGCAGAAGAA
CTCAATCTCGGGAATCTCAATGTTAGTATTCCCTGGACTCATAAGGTGGGAAACTTTACG
GGGCTTTATTCTTCTACTGTTCCTGTCTTTAACCCTCATTGGAAAACACCCTCTTTTCCT
AATATACATTTACACCAAGACATTATCAAAAAATGTGAACAATTTGTAGGCCCACTCACA
GTCAATGAGAAAAGAAGACTGCAATTGATTATGCCTGCTAGGTTTTATCCAAAGGTTACC
AAATATTTGCCATTGGATAAGGGTATTAAACCTTATTATCCAGAACATCTAGTTAATCAT
TACTTCCAAACCAGACATTATTTACACACTCTATGGAAGGCGGGTGTATTATATAAGAGA
GAAACTACACATAGCGCCTCATTTTGTGGGTCACCATATTCCTGGGAACAAGAGCTACAG
CATGGGGCAGAATCTTTCCACCAGCAATCCTCTGGGATTCTTTCCCGACCACCAGTTGGA
TCCAGCCTTCAGAGCAAACACTGCAAATCCAGATTGGGACTTCAATCCCAACAAGGACTC
CTGGCCAGACGCCAACAAGGTAGGAGCTGGAGCATTCGGGCTGGGATTCACCCCACCGCA
CGGAGGCCTTTTGGGGTGGAGCCCTCAGGCTCAGGGCATACTACAAACCTTGCCAGCAAA
TCCGCCTCCTGCCTCCACCAATCGCCAGTCAGGAAGGCAACCTACCCCTCTGTCTCCACC
TTTGAGAAACACTCATCCTCAGGCCATGCAGTGGAACTCCACAACCTTCCACCAAACTCT
GCAAGATCCCAGAGTGAGAGGCCTGTATCTCCCTGCTGGTGGCTCCAGTTCAGGAACAGT
AAACCCTGTTCCGACTACTGTCTCTCCCATATCGTCAATCTTCTCGAGGATTGGGGACCC
TGCGCTGAACATGGAGAACATCACATCAGGATTCCTAGGACCCCTGCTCGTGTTACAGGC
GGGGTTTTTCTTGTTGACAAAAATCCTCACAATACCGAAGAGTCTAGACTCGTGGTGGAC
TTCTCTCAATTTTCTAGGGGGAACCACCGTGTGTCTTGGCCAAAATTCGCAGTCCCCAAC
CTCCAATCACTCACCAACCTCCTGTCCTCCAACTTGTCCTGGTTATCGCTGGATGTGTCT
GCGGCGTTTTATCATCTTCCTCTTCATCCTGCTGCTATGCCTCATCTTCTTGTTGGTTCT
TCTGGACTATCAAGGTATGTTGCCCGTTTGTCCTCTGATTCCAGGATCTTCAACCACCAG
CACGGGACCATGCAGAACCTGCACGACTCCTGCTCAAGGAACCTCTATGTATCCCTCCTG
TTGCTGTACCAAACCTTCGGACGGAAATTGCACCTGTATTCCCATCCCATCATCCTGGGC
TTTCGGAAAATTCCTATGGGAGTGGGCCTCAGCCCGTTTCTCCTGGCTCAGTTTACTAGT
GCCATTTGTTCAGTGGTTCGTAGGGCTTTCCCCCACTGTTTGGCTTTTAGTTATATGGAT
GATGTGGTATTGGGGGCCAAAACTGTTCACCATCTTGAGTCCCTTTTTACCGCTGTTACC
AATTTTCTTTTGTCTTTGGGTATACATCTAAACCCTAACAAAACAAAAAGATGGGGTTAC
TCTTTACATTTTATGGGCTATGTCATTGGATGTTATGGGTCTTTGCCACAAGATCACATC
ATACAGAAAATCAAAGAATGTTTTAGAAAACTTCCTGTTAACAGGCCTATTGATTGGAAA
GTCTGTCAACGTATTGTGGGTCTTTTGGGATTTGCTGCTCCTTTTACACAATGTGGTTAT
CCTGCTTTAATGCCCTTGTATGCATGTATTCAATCTAAGCAGGCTTTCACTTTCTCGCCA
ACTTACAAGGCCTTTCTGTGTAAACAATACCTGAACCTTTACCCCGTTGCCCGGCAACGC
CCAGGTCTGTGCCAAGTGTTTGCTGACGCAACCCCCACTGGCTGGGGCTTGGTCATGGGC
CATCAGCGCATGCGTGGAACCTTTCAGGCTCCTCTGCCGATCCATACTGCGGAACTCCTA
GCCGCTTGTTTTGCTCGCAGCCGGTCTGGAGCAAACATTCTCGGGACGGATAACTCTGTT
GTTCTCTCCCGCAAATATACGTCGTTTCCATGGCTGCTAGGCTGTGCTGCCAACTGGATC
CTGCGCGGGACGTCCTTTGTTTACGTCCCGTCGGCGCTGAATCCCGCGGACGACCCTTCT
CGGGGCCGCTTGGGACTCTCTCGTCCCCTTCTCCGTCTGCCGTTTCGACCGACCACGGGG
CGCACCTCTCTTTACGCGGACTCCCCGTCTGTGCCTTCTCATCTGCCGGACCGTGTGCAC
TTCGCTTCACCTCTGCACGTCGCATGGAGACCACCGTGA
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. Tong SP, Li JS, Vitvitski L, Trepo C: Active hepatitis B virus replication in the presence of anti-HBe is associated with viral variants containing an inactive pre-C region. Virology. 1990 Jun;176(2):596-603. [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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