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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:56 UTC
HMDB IDHMDB0014585
Secondary Accession Numbers
  • HMDB14585
Metabolite Identification
Common NameEntecavir
DescriptionEntecavir, also known as baraclude, belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others. Entecavir is a drug which is used 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. Entecavir is not a substrate, inhibitor, or inducer of the cytochrome P450 (CYP450) enzyme system. 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. Entecavir is a guanosine nucleoside analogue with selective activity against hepatitis B virus (HBV). 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. Entecavir is a moderately basic compound (based on its pKa). Entecavir is an oral antiviral drug used in the treatment of hepatitis B infection. 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 is marketed under the trade name Entecavir (BMS).
Structure
Data?1582753196
Synonyms
ValueSource
BaracludeHMDB
EntecavirChEBI
Chemical FormulaC12H15N5O3
Average Molecular Weight277.2792
Monoisotopic Molecular Weight277.117489371
IUPAC Name2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one
Traditional Nameentecavir
CAS Registry Number142217-69-4
SMILES
NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](CO)C1=C
InChI Identifier
InChI=1S/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
InChI KeyQDGZDCVAUDNJFG-FXQIFTODSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassNucleoside and nucleotide analogues
Sub ClassNot Available
Direct ParentNucleoside and nucleotide analogues
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Purinone
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Pyrimidone
  • Cyclopentanol
  • Pyrimidine
  • N-substituted imidazole
  • Azole
  • Cyclic alcohol
  • Heteroaromatic compound
  • Imidazole
  • Vinylogous amide
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Primary amine
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.59 g/LNot Available
LogP-0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.59 g/LALOGPS
logP-0.81ALOGPS
logP-1.4ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8ChemAxon
pKa (Strongest Basic)2.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71 m³·mol⁻¹ChemAxon
Polarizability27.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-3190000000-4c1e30013236fcf851e8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4l-4009600000-59f2f642d2b55baa6f98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0090000000-fece17372f19f5c56b9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-4190000000-2224afe131c0d7ffddebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2940000000-a8c2e92ba3db7d5cb611Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f7f436db2922d84e90deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kdi-0290000000-c1ee67566ff6950ae6f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfu-5930000000-de30bdfb529397180104Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00442 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00442 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00442
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID135679
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEntecavir
METLIN IDNot Available
PubChem Compound153941
PDB IDNot Available
ChEBI ID473990
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available