Entecavir is a nucleoside analogue used in the treatment of chronic hepatitis B for patients with active viral replication, histological evidence of active disease, or persistent elevations in liver transaminases.
- Brand Names
- Generic Name
- DrugBank Accession Number
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.
- Small Molecule
- Approved, Investigational
- Average: 277.2792
- Chemical Formula
- Anhydrous entecavir
- Entecavir (anhydrous)
- Entecavir anhydrous
- External IDs
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.Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.
- Associated Conditions
- 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.
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. Upon activation by kinases, the drug can be incorporated into the DNA which has the ultimate effect of inhibiting the HBV polymerase activity.
Target Actions Organism ADNAother Humans
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.
- Volume of distribution
- Protein binding
Binding of entecavir to human serum proteins in vitro is approximately 13%.
Entecavir is not a substrate, inhibitor, or inducer of the cytochrome P450 (CYP450) enzyme system. Entecavir is efficiently phosphorylated to the active triphosphate form.
- Route of elimination
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.
- renal cl=383.2 +/- 101.8 mL/min [Unimpaired renal function]
- renal cl=197.9 +/- 78.1 mL/min [Mild impaired renal function]
- renal cl=135.6 +/- 31.6 mL/min [Moderate impaired renal function]
- renal cl=40.3 +/- 10.1 mL/min [severe impaired renal function]
- apparent oral cl=588.1 +/- 153.7 mL/min [Unimpaired renal function]
- apparent oral cl=309.2 +/- 62.6 mL/min [Mild impaired renal function]
- apparent oral cl=226.3 +/- 60.1 mL/min [Moderate impaired renal function]
- apparent oral cl=100.6 +/- 29.1 mL/min [severe impaired renal function]
- apparent oral cl=50.6 +/- 16.5 mL/min [severe impaired renal function amnaged with Hemodialysis]
- apparent oral cl=35.7 +/- 19.6 mL/min [severe impaired renal function amnaged with CAPD]
- 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.
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.
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
- 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 Abametapir The serum concentration of Entecavir can be increased when it is combined with Abametapir. Abatacept The metabolism of Entecavir can be increased when combined with Abatacept. Abiraterone The serum concentration of Entecavir can be increased when it is combined with Abiraterone. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Entecavir. Acetaminophen The metabolism of Entecavir can be decreased when combined with Acetaminophen. Acyclovir The metabolism of Acyclovir can be decreased when combined with Entecavir. Adalimumab The metabolism of Entecavir can be increased when combined with Adalimumab. Adenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Entecavir. Agomelatine The metabolism of Agomelatine can be decreased when combined with Entecavir. Albendazole The metabolism of Entecavir can be increased when combined with Albendazole.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 on an empty stomach. Take 2 hours before or 2 hours after a meal.
- 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.
- Product Ingredients
Ingredient UNII CAS InChI Key Entecavir monohydrate 5968Y6H45M 209216-23-9 YXPVEXCTPGULBZ-WQYNNSOESA-N Entecavir triphosphate Not Available Not Available ZTWBIZVVFNIRSF-HAFWLYHUSA-N
- Product Images
- International/Other Brands
- Barcavir (Incepta) / Caavirel (PMP) / Entaliv (Dr. Reddy's Laboratories) / Teviral (ACI)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Baraclude Solution 0.05 mg/1mL Oral E.R. Squibb & Sons, L.L.C. 2005-03-29 Not applicable Baraclude Solution 0.05 mg/ml Oral Bristol Myers Squibb Pharma Eeig 2016-09-08 Not applicable Baraclude Tablet, film coated 1 mg Oral Bristol Myers Squibb Pharma Eeig 2016-09-08 Not applicable Baraclude Tablet, film coated 1 mg Oral Bristol Myers Squibb Pharma Eeig 2016-09-08 Not applicable Baraclude Tablet, film coated 1.0 mg/1 Oral E.R. Squibb & Sons, L.L.C. 2005-03-29 Not applicable Baraclude Tablet, film coated 1 mg Oral Bristol Myers Squibb Pharma Eeig 2016-09-08 Not applicable Baraclude Tablet 0.5 mg Oral Bristol Myers Squibb 2006-09-12 Not applicable Baraclude Tablet, film coated 0.5 mg Oral Bristol Myers Squibb Pharma Eeig 2016-09-08 Not applicable Baraclude Tablet, film coated 0.5 mg Oral Bristol Myers Squibb Pharma Eeig 2016-09-08 Not applicable Baraclude Tablet, film coated 0.5 mg Oral Bristol Myers Squibb Pharma Eeig 2016-09-08 Not applicable
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Accel-entecavir Tablet 0.5 mg Oral Accel Pharma Inc 2020-03-11 Not applicable Apo-entecavir Tablet 0.5 mg Oral Apotex Corporation 2013-01-18 Not applicable Auro-entecavir Tablet 0.5 mg Oral Auro Pharma Inc 2015-12-01 Not applicable Entecavir Tablet, film coated 0.5 mg/1 Oral Northstar RxLLC 2017-06-15 Not applicable Entecavir Tablet 0.5 mg/1 Oral Breckenridge Pharmaceutical, Inc. 2018-03-16 Not applicable Entecavir Tablet, film coated 1 mg/1 Oral AvKARE 2020-11-02 Not applicable Entecavir Tablet 1 mg/1 Oral Florida Pharmaceutical Products, LLC 2021-02-26 Not applicable Entecavir Tablet, film coated 1 mg/1 Oral Golden State Medical Supply, Inc. 2017-08-25 2022-04-30 Entecavir Tablet, film coated 0.5 mg/1 Oral Solco Healthcare Llc 2018-04-01 Not applicable Entecavir Tablet, film coated 0.5 mg/1 Oral Par Pharmaceutical 2014-08-18 2017-08-31
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BARACLUDE 0,5 MG FILM TABLET, 30 ADET Entecavir monohydrate (0.5 mg) Tablet, film coated Oral BRISTOL-MYERS SQUIBB İLAÇLARI INC. İSTANBUL ŞUBESİ 2020-08-14 Not applicable BARACLUDE 1 MG FILM TABLET, 30 ADET Entecavir monohydrate (1 mg) Tablet, film coated Oral BRISTOL-MYERS SQUIBB İLAÇLARI INC. İSTANBUL ŞUBESİ 2020-08-14 Not applicable HEDNAVIR 0,5 MG FILM TABLET, 30 ADET Entecavir monohydrate (0.5 mg) Tablet, film coated Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable HEDNAVIR 1 MG FILM TABLET, 30 ADET Entecavir monohydrate (1 mg) Tablet, film coated Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable
- ATC Codes
- J05AF10 — Entecavir
- Drug Categories
- Anti-Infective Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 Substrates
- Direct Acting Antivirals
- Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor
- Heterocyclic Compounds, Fused-Ring
- Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
- Nucleoside Reverse Transcriptase Inhibitors
- Nucleosides and Nucleotides
- Chemical TaxonomyProvided by Classyfire
- This compound 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.
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Nucleoside and nucleotide analogues
- Sub Class
- Not Available
- Direct Parent
- Nucleoside and nucleotide analogues
- Alternative Parents
- Hypoxanthines / 6-oxopurines / Pyrimidones / Aminopyrimidines and derivatives / N-substituted imidazoles / Cyclopentanols / Vinylogous amides / Heteroaromatic compounds / Cyclic alcohols and derivatives / Azacyclic compounds / Primary amines / Primary alcohols / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives show 5 more
- 6-oxopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Cyclic alcohol / Cyclopentanol / Heteroaromatic compound / Hydrocarbon derivative / Hypoxanthine / Imidazole / Imidazopyrimidine / N-substituted imidazole / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Primary alcohol / Primary amine / Purine / Purinone / Pyrimidine / Pyrimidone / Secondary alcohol / Vinylogous amide show 20 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- secondary alcohol, oxopurine, primary alcohol, 2-aminopurines (CHEBI:473990)
- Affected organisms
- Hepatitis B virus
- CAS number
- InChI Key
- IUPAC Name
- Synthesis Reference
- General References
- Not Available
- FDA label
- Download (628 KB)
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Exposure to Hepatitis B Virus / Reactivation of hepatitis B virus infection / Rheumatoid Arthritis 1 4 Active Not Recruiting Treatment Cirrhosis of the Liver / Viral Hepatitis B 1 4 Active Not Recruiting Treatment HBV Coinfection / HCC 1 4 Active Not Recruiting Treatment Hepatitis B Chronic Infection 1 4 Active Not Recruiting Treatment Viral Hepatitis B 1 4 Completed Prevention Non-Hodgkin's Lymphoma (NHL) / Viral Hepatitis B 1 4 Completed Treatment Chronic Viral Hepatitis B Without Delta-agent 2 4 Completed Treatment Cirrhosis of the Liver 2 4 Completed Treatment Fibrosis, Liver 1 4 Completed Treatment HBeAg Positive Chronic Hepatitis B 1
- Bristol myers squibb
- Bristol-Myers Squibb Co.
- E.R. Squibb and Sons LLC
- Dosage Forms
Form Route Strength Solution Oral 0.05 MG/ML Solution Oral 0.05 mg/1mL Tablet, film coated Oral 1.0 MG Solution Oral 5 mg Tablet, coated Oral 1 mg Tablet Oral Tablet Oral 0.5 mg/1 Tablet Oral 1 mg/1 Tablet, coated Oral 0.5 mg/1 Tablet, coated Oral 1 mg/1 Tablet, film coated Oral 0.5 mg/1 Tablet, film coated Oral 1 mg/1 Tablet, film coated Oral 1.0 mg/1 Tablet, film coated Oral 1.00 mg Tablet, film coated Oral Tablet, film coated Oral 1.064 Mg Tablet, coated Oral 0.5 mg Tablet Oral 0.5 mg Tablet, soluble Oral 0.5 Mg Tablet Oral 1 mg Tablet, film coated Oral 0.50 mg Tablet, film coated Oral 0.53 Mg Tablet, film coated Oral 0.5 mg Tablet, film coated Oral 1 mg
Unit description Cost Unit Baraclude 0.5 mg tablet 28.94USD tablet Baraclude 1 mg tablet 28.94USD tabletDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2053339 No 2001-05-29 2011-10-11 US5206244 Yes 1993-04-27 2015-08-21
- Experimental Properties
Property Value Source water solubility Slightly soluble (2.4 mg/mL at pH 7.9, 25 °C) Not Available logP -0.8 Not Available
- Predicted Properties
Property Value Source Water Solubility 6.59 mg/mL ALOGPS logP -0.81 ALOGPS logP -1.4 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 8 ChemAxon pKa (Strongest Basic) 2.77 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 125.76 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 71 m3·mol-1 ChemAxon Polarizability 27.31 Å3 ChemAxon Number of Rings 3 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 + 1.0 Blood Brain Barrier + 0.873 Caco-2 permeable - 0.7601 P-glycoprotein substrate Substrate 0.5802 P-glycoprotein inhibitor I Non-inhibitor 0.863 P-glycoprotein inhibitor II Non-inhibitor 0.9185 Renal organic cation transporter Non-inhibitor 0.8465 CYP450 2C9 substrate Non-substrate 0.8817 CYP450 2D6 substrate Non-substrate 0.8164 CYP450 3A4 substrate Non-substrate 0.5346 CYP450 1A2 substrate Non-inhibitor 0.7641 CYP450 2C9 inhibitor Non-inhibitor 0.848 CYP450 2D6 inhibitor Non-inhibitor 0.915 CYP450 2C19 inhibitor Non-inhibitor 0.87 CYP450 3A4 inhibitor Non-inhibitor 0.9647 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9552 Ames test Non AMES toxic 0.7523 Carcinogenicity Non-carcinogens 0.8026 Biodegradation Not ready biodegradable 0.9669 Rat acute toxicity 2.3879 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8865 hERG inhibition (predictor II) Non-inhibitor 0.9062
- Mass Spec (NIST)
- Not Available
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
- Sims KA, Woodland AM: Entecavir: a new nucleoside analog for the treatment of chronic hepatitis B infection. Pharmacotherapy. 2006 Dec;26(12):1745-57. [Article]
- Walsh AW, Langley DR, Colonno RJ, Tenney DJ: Mechanistic characterization and molecular modeling of hepatitis B virus polymerase resistance to entecavir. PLoS One. 2010 Feb 12;5(2):e9195. doi: 10.1371/journal.pone.0009195. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 27, 2022 17:28