Entecavir

Highest phase reached

Approved

www.ebi.ac.uk

Drug type

Small molecule

www.ebi.ac.uk

First approval year

2005

www.ebi.ac.uk

First approval year: 2005
www.ebi.ac.uk

Listing at source: Listed

Highest phase reached: Approved
www.ebi.ac.uk

Drug type: Small molecule
www.ebi.ac.uk

Drug name: Entecavir
www.ebi.ac.uk

Molecular weight: 295.3
www.ebi.ac.uk

Structure (SMILES): C=C1[C@H](CO)[C@@H](O)C[C@@H]1n1cnc2c(=O)[nH]c(N)nc21.O
www.ebi.ac.uk

baraclude
Baraclude
entecavir
Entecavir
entecavir accord
Entecavir accord
entecavir mylan
Entecavir mylan
Entecavir viatris (previously entecavir mylan)
entecavir viatris previously entecavir mylan

(Baraclude 0.5mg Tablets
0.5mg Baraclude(entecavir)
Baraclude
baraclude 0 5mg tablets
Baraclude tablets
bms 200475 01
BMS-200475-01
entecavir
Entecavir
entecavir (BARACLUDE®)
Entecavir (ETV)
Entecavir (ETV) monohydrate
ENTECAVIR [EMA EPAR]
ENTECAVIR [MART.]
ENTECAVIR [ORANGE BOOK]
ENTECAVIR [USAN]
ENTECAVIR [USP MONOGRAPH]
ENTECAVIR [VANDF]
entecavir 0.5 mg
Entecavir 0.5 mg
Entecavir 1 MG
Entecavir 1Mg Oral Tablet
entecavir ema epar
entecavir hydrate
Entecavir hydrate

And 25 more, listed on the interactive page.

ATC classification codes

J05AF10

Sources for recorded values

www.ebi.ac.uk

ChEMBL ID: CHEMBL5314362
www.ebi.ac.uk

InChIKey: YXPVEXCTPGULBZ-WQYNNSOESA-N
www.ebi.ac.uk

PubChem compound IDs

135526609

RxNorm IDs (RxCUI)

306266

FDA ingredient codes (UNII)

5968Y6H45M

142217-69-4
209216-23-9

Applicant: BRISTOL MYERS SQUIBB
Approval date: 29 Mar 2005
Application number: NDA021797

Status: Authorised
Status date: 26 Jun 2006
Authorisation date: 26 Jun 2006
Approved indications: Baraclude is indicated for the treatment of chronic hepatitis B virus (HBV) infection in adults with: compensated liver disease and evidence of active viral replication, persistently elevated serum alanine aminotransferase (ALT) levels and histological evidence of active inflammation and/or fibrosis; decompensated liver disease. For both compensated and decompensated liver disease, this indication is based on clinical trial data in nucleoside naive patients with HBeAg positive and HBeAg negative HBV infection. With respect to patients with lamivudine-refractory hepatitis B.
Product number: EMEA/H/C/000623
Authorisation holder: Bristol-Myers Squibb Pharma EEIG
Priority medicines scheme: No
Generic: No
Biosimilar: No
Generic medicines: 2
Biosimilar medicines: 0
Advanced therapy: No
Conditional approval: No
Additional monitoring: No
Accelerated assessment: No
Exceptional circumstances: No

Therapeutic areas

Hepatitis B, Chronic

European medicines record

www.ema.europa.eu

Patents: 0
Designations: 1
First in class: No
Fast track: No
Breakthrough designation: No
Orphan designation: No
Priority review: Yes
Orphan exclusivity: No
Accelerated approval: No
Availability: Prescription only
Boxed warning: Yes

Drug name stem: -vir

Administration routes

Oral

Mechanisms of action

Mechanism
DNA polymerase/reverse transcriptase inhibitor
Action type
Inhibitor
Target
DNA polymerase/reverse transcriptase
Protein identifier
Q9IF40

Open Targets mechanisms

Mechanism
DNA polymerase/reverse transcriptase inhibitor
Action type
Inhibitor
Target
DNA polymerase/reverse transcriptase

DrugCentral mechanisms

Action type
Inhibitor
Gene symbol
P
Protein identifier
Q9IF40
Organism
Hepatitis B virus

Condition
Carcinoma, Hepatocellular
Highest recorded phase
3
Condition identifier
EFO:0000182
Subject identifier
D006528
Condition
Infections
Highest recorded phase
2
Condition identifier
EFO:0000544
Subject identifier
D007239
Condition
Virus Diseases
Highest recorded phase
4
Condition identifier
EFO:0000763
Subject identifier
D014777
Condition
Liver Diseases
Highest recorded phase
4
Condition identifier
EFO:0001421
Subject identifier
D008107
Condition
Stomach Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0003897
Subject identifier
D013274
Condition
Colorectal Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0004142
Subject identifier
D015179
Condition
Hepatitis B
Highest recorded phase
4
Condition identifier
EFO:0004197
Subject identifier
D006509
Condition
Hepatitis B, Chronic
Highest recorded phase
4
Condition identifier
EFO:0004197
Subject identifier
D019694
Condition
Hepatitis C, Chronic
Highest recorded phase
2
Condition identifier
EFO:0004220
Subject identifier
D019698
Condition
Hepatitis B, Chronic
Highest recorded phase
4
Condition identifier
EFO:0004239
Subject identifier
D019694
Condition
Hepatitis D
Highest recorded phase
2
Condition identifier
EFO:0007304
Subject identifier
D003699
Condition
Liver Neoplasms
Highest recorded phase
2
Condition identifier
MONDO:0002691
Subject identifier
D008113
Condition
Liver Failure
Highest recorded phase
2
Condition identifier
MONDO:0100192
Subject identifier
D017093

Condition identifier
EFO_0000182
Highest recorded phase
3
Condition identifier
EFO_0000544
Highest recorded phase
2
Condition identifier
EFO_0000763
Condition identifier
EFO_0001421
Condition identifier
EFO_0003897
Highest recorded phase
2
Condition identifier
EFO_0004142
Highest recorded phase
2
Condition identifier
EFO_0004197
Condition identifier
EFO_0004239
Condition identifier
EFO_0005952
Highest recorded phase
2
Condition identifier
EFO_0007949
Condition identifier
HP_0001394
Condition identifier
HP_0001395
Highest recorded phase
2
Condition identifier
HP_0002910
Condition identifier
HP_0002910
Highest recorded phase
4
Condition identifier
MONDO_0002691
Condition identifier
MONDO_0004790
Condition identifier
MONDO_0005108
Highest recorded phase
4
Condition identifier
MONDO_0005154
Highest recorded phase
4
Condition identifier
MONDO_0005155
Condition identifier
MONDO_0005300
Condition identifier
MONDO_0005344
Highest recorded phase
4
Condition identifier
MONDO_0005354
Highest recorded phase
2
Condition identifier
MONDO_0005366
Highest recorded phase
4
Condition identifier
MONDO_0005789
Highest recorded phase
2
Condition identifier
MONDO_0007256
Highest recorded phase
3

And 5 more, listed on the interactive page.

Warning
Black Box Warning
Effect
hepatotoxicity
Warning
Black Box Warning
Effect
immune system toxicity
Warning
Black Box Warning
Effect
metabolic toxicity

Warning
Black Box Warning
Effect
hepatotoxicity
Country
United States
Warning
Black Box Warning
Effect
immune system toxicity
Country
United States
Warning
Black Box Warning
Effect
metabolic toxicity
Country
United States

Event
abortion induced
Reports
24
Reporting signal score
36.2516
Event
alanine aminotransferase increased
Reports
53
Reporting signal score
33.2107
Event
blood creatine phosphokinase increased
Reports
35
Reporting signal score
26.9692
Event
blood creatinine increased
Reports
50
Reporting signal score
35.6799
Event
blood hiv rna decreased
Reports
18
Reporting signal score
115.153
Event
blood phosphorus decreased
Reports
24
Reporting signal score
62.7865
Event
drug hypersensitivity
Reports
3
Reporting signal score
28.6821
Event
drug resistance
Reports
219
Reporting signal score
634.59
Event
fanconi syndrome
Reports
14
Reporting signal score
38.6244
Event
genotype drug resistance test
Reports
30
Reporting signal score
194.336
Event
genotype drug resistance test positive
Reports
26
Reporting signal score
86.2631
Event
hepatic cancer
Reports
39
Reporting signal score
126.365
Event
hepatic cirrhosis
Reports
35
Reporting signal score
60.7726
Event
hepatic neoplasm malignant
Reports
30
Reporting signal score
115.211
Event
hepatitis b
Reports
70
Reporting signal score
220.194
Event
hepatitis b dna increased
Reports
56
Reporting signal score
270.285
Event
hepatitis b reactivation
Reports
35
Reporting signal score
106.53
Event
hepatocellular carcinoma
Reports
49
Reporting signal score
124.255
Event
hypotension
Reports
2
Reporting signal score
26.8703
Event
liver transplant
Reports
15
Reporting signal score
33.3366
Event
multiple-drug resistance
Reports
47
Reporting signal score
167.583
Event
pain
Reports
9
Reporting signal score
32.7475
Event
pathogen resistance
Reports
82
Reporting signal score
239.437
Event
renal impairment
Reports
76
Reporting signal score
71.0557
Event
viraemia
Reports
10
Reporting signal score
27.8979

And 3 more, listed on the interactive page.

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And 128 more, listed on the interactive page.

Dose: 0.5 mg
How often: Once daily

Conditions of use

Administer on an empty stomach at least 2 hours after a meal and 2 hours before the next meal

Hydrogen bond acceptors: 7
Hydrogen bond donors: 4
Polar surface area: 130.05
Calculated partition coefficient (ALogP): -0.83
Prodrug: Yes
Chirality: Single enantiomer
Inorganic: No
Rule-of-five violations: 0
Rotatable bonds: 2
Heavy atoms: 21
Molecular formula: C12H17N5O4
Monoisotopic mass: 295.12805404
Natural product: No

0003-1611
0003-1612
0003-1614
16714-717
16714-718
42291-261
42806-658
42806-659
50771-013
50771-014
51407-589
60687-216
61442-311
65162-446
65162-449
65862-841
65862-842
68382-920
68382-921
69097-425
69097-426
70771-1019
70771-1020

Recorded assays: 310
Active assays: 77

Active assay types

Confirmatory

Oral bioavailability

Median: 100
Mean: 100
Minimum: 100
Maximum: 100
Unit: %
Assays: 1
Standard deviation: 0
Summary method: median
Censored results excluded: 0
Other units excluded: 0
Unknown units excluded: 0

Measurement types

Related records

Trials (227)

3E Extension Study
A Clinical Study of APG-1387 in Combination With Entecavir in Patients With Chronic Hepatitis B
A Clinical Study of TQA3605 Tablets Monotherapy or in Combination With Nucleoside (Acid) Analogues in Treatment Naive and Treated Patients With Chronic Hepatitis B
A Clinical Trial on Hepatitis B Vaccine Activated-Dendritic Cells Combined With Anti-HBV Drugs in CHB
A Clinical Trial to Evaluate the Efficacy and Safety of TQA3605 Tablets in Treatment-naive Chronic HBV-infected Subjects
A Drug-drug Interaction (DDI) Study of Morphothiadine Mesilate/Ritonavir in Healthy Subjects
A Multi-dose Study of ARC-520 in Patients With Hepatitis B 'e' Antigen (HBeAg) Negative, Chronic Hepatitis B Virus (HBV) Infection
A Multi-dose Study of ARC-520 in Patients With Hepatitis B 'e' Antigen (HBeAg) Positive, Chronic Hepatitis B Virus Infection
A Multicenter Study to Determine the Depth and Duration of Hepatitis B Surface Antigen (HBsAg) Reduction After Single or Multiple Doses of ARC-520, in Combination With Entecavir in Patients With Chronic Hepatitis B Virus (HBV) Infection
A Phase 1 Study to Evaluate the Safety and Pharmacokinetics of Entecavir Extended Release (XR) in Healthy Subjects
A Phase II Clinical Trial of Hydronidone Capsules(F351) in Patients With Liver Fibrosis Induced by HBV Chronic Hepatitis
A Phase II Dose Response Study in Japan in Chronic Hepatitis B
A Phase III Study of Entecavir vs Lamivudine in Adults With Chronic Hepatitis B Infection and Negative for Hepatitis B e Antigen
A Phase III Study of Entecavir vs Lamivudine in Adults With Chronic Hepatitis B Infection and Positive for Hepatitis B E Antigen
A Phase III Study of Entecavir vs Lamivudine in Chronic Hepatitis B Subjects With Incomplete Response to Lamivudine
A Phase III Study of the Safety and Efficacy of Entecavir in Pediatric Patients With Chronic Hepatitis B Virus Infection
A Phase III Study to Evaluate the Efficacy and Safety of ZM-H1505R in Patients With CHB
A Phase IIIb Study to Compare Entecavir Plus Tenofovir vs. Adefovir Added to Continuing Lamivudine Therapy in Adult Patients With Lamivudine-Resistant Hepatitis B Infection
A Prospective Clinical Trial in Chronic Hepatitis B Patients NAs (Nucleotides or Nucleosides) Experienced (Anchor Study)
A Randomized Controlled Trial on the Efficacy of Tenofovir Disoproxil Fumarate (TDF)-Switch Therapy in Chronic Hepatitis B Patients With Incomplete Response to Entecavir

Approved for (4)

In development for (8)

Chronic hepatitis C virus infection Phase 2
Colorectal neoplasm Phase 2
Gastric neoplasm Phase 2
Hepatitis D virus infection Phase 2
Hepatocellular carcinoma Phase 3
Liver cancer Phase 2
Liver failure Phase 2
Non-Hodgkin lymphoma Phase 2

Entecavir

Development status

Names and chemistry

Brand names (10)

Other names (50)

Identifiers

CAS registry numbers (2)

Regulatory information

United States

European Union

Therapeutic areas

Other regulatory facts

Pharmacology

Drug classification

Administration routes

Mechanisms of action

Open Targets mechanisms

DrugCentral mechanisms

Investigated indications (13)

Open Targets indications (30)

Warnings (3)

Open Targets warnings (3)

Reported adverse events (28)

Trial references (153)

Dosing

Conditions of use

Chemical properties

National Drug Codes

Evidence counts

Active assay types

Biological measurements

Observed measurements

Oral bioavailability

Measurement types

Related records

Trials (227)

Approved for (4)

In development for (8)