Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H15N5O3.C4H4O4 |
Molecular Weight | 393.352 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C=C1[C@]([H])(CO)[C@]([H])(C[C@]1([H])n2cnc3c2[nH]c(=N)nc3O)O.C(\[H])(=C(\[H])/C(=O)O)/C(=O)O
InChI
InChIKey=UEXBBJAYBDAHLG-FJESMAGSSA-N
InChI=1S/C12H15N5O3.C4H4O4/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20;5-3(6)1-2-4(7)8/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20);1-2H,(H,5,6)(H,7,8)/b;2-1-/t6-,7-,8-;/m0./s1
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0723 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Molecular Formula | C12H15N5O3 |
Molecular Weight | 277.2797 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment:: Description was created based on several resourses, including http://www.drugs.com/monograph/entecavir.html and http://www.drugbank.ca/drugs/DB00442
Curator's Comment:: Description was created based on several resourses, including http://www.drugs.com/monograph/entecavir.html and http://www.drugbank.ca/drugs/DB00442
BARACLUDE® is the tradename for entecavir, a guanosine nucleoside analogue with selective activity against hepatitis B virus (HBV). It inhibits all three steps in the viral replication process. 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. Entecavir 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.
CNS Activity
Sources: http://www.hc-sc.gc.ca/dhp-mps/alt_formats/hpfb-dgpsa/pdf/prodpharma/sbd_smd_2007_baraclude_102555-eng.pdf
Curator's Comment:: Low concentrations of entecavir were found in the cerebrospinal fluid of mice, rats, dogs and monkeys indicating that entecavir can cross the blood brain barrier.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 Sources: http://www.drugbank.ca/drugs/DB00442 |
0.004 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Entecavir Approved UseBARACLUDE (entecavir) is indicated 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. Launch Date1.11205443E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.23 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17050790/ |
0.5 mg 1 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENTECAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.24 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17050790/ |
1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENTECAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.1 ng/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENTECAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.2 ng/mL |
0.5 mg 1 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENTECAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.78 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17050790/ |
0.5 mg 1 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENTECAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
26.38 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17050790/ |
1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENTECAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
27.9 ng × h/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENTECAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
129.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17050790/ |
0.5 mg 1 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENTECAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
148.89 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17050790/ |
1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENTECAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
138.5 h |
0.5 mg 1 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENTECAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
87% |
0.5 mg 1 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENTECAVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1 mg 1 times / day steady, oral Highest studied dose Dose: 1 mg, 1 times / day Route: oral Route: steady Dose: 1 mg, 1 times / day Sources: Page: 6.1 |
unhealthy, adult n = 183 Health Status: unhealthy Condition: hepatitis B Age Group: adult Sex: unknown Population Size: 183 Sources: Page: 6.1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 42.0 |
inconclusive | |||
Page: 42, 154, 155 |
no [IC50 >300 uM] | no (co-administration study) Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with phenacetin Page: 42, 154, 155 |
||
Page: 42, 154, 155 |
no [IC50 >300 uM] | no (co-administration study) Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with S-mephentytoin Page: 42, 154, 155 |
||
Page: 42, 154, 155 |
no [IC50 >300 uM] | no (co-administration study) Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with S-mephentytoin Page: 42, 154, 155 |
||
Page: 42, 154, 155 |
no [IC50 >300 uM] | no (co-administration study) Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with diclofenac Page: 42, 154, 155 |
||
Page: 42, 154, 155 |
no [IC50 >300 uM] | no (co-administration study) Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with bufuralol Page: 42, 154, 155 |
||
Page: 42, 154, 155 |
no [IC50 >300 uM] | no (co-administration study) Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with p-nitrophenol Page: 42, 154, 155 |
||
Page: 42, 154, 155 |
no [IC50 >300 uM] | no (co-administration study) Comment: at clinically relevant concentrations entecavir inhibitied catalytic activities no greater than 9% with testosterone Page: 42, 154, 155 |
||
Page: 4, 16 |
no | |||
Page: 4, 16 |
no | |||
Page: 17.0 |
no | |||
Page: 17.0 |
no | |||
Page: 17.0 |
no | |||
Page: 17.0 |
no | |||
Page: 17.0 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 46.0 |
likely | |||
Page: 4, 16 |
no | |||
Page: 5.0 |
no | |||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 12, 13, 14 |
PubMed
Title | Date | PubMed |
---|---|---|
[Entecavir therapy against hepatitis B]. | 2004 Aug |
|
[Treatment and selection criteria for chronic hepatitis B]. | 2004 Aug |
|
[Recent advances in the treatment of fulminant hepatitis B]. | 2004 Aug |
|
[Advances in the treatment of acute hepatitis B]. | 2004 Aug |
|
Management of hepatitis B patients with antiviral resistance. | 2004 Dec |
|
Entecavir for the treatment of chronic hepatitis B. | 2004 Dec |
|
Gateways to clinical trials. | 2004 Nov |
|
Emerging treatments in chronic hepatitis B. | 2004 Nov |
|
[Treatment of hepatitis B]. | 2004 Nov 7 |
|
Gateways to clinical trials. | 2004 Sep |
|
Cross-resistance testing of next-generation nucleoside and nucleotide analogues against lamivudine-resistant HBV. | 2005 |
|
Management of HBV/HIV-coinfected Patients. | 2005 |
|
Clinical trial results of new therapies for HBV: implications for treatment guidelines. | 2005 |
|
Current treatment of chronic hepatitis B: benefits and limitations. | 2005 |
|
Drugs in development for hepatitis B. | 2005 |
|
US approves new HBV drug. | 2005 Apr |
|
Managing hepatitis B coinfection in HIV-infected patients. | 2005 Aug |
|
The current status of antiviral therapy of chronic hepatitis B. | 2005 Dec |
|
Hepatitis B virus infection: current status. | 2005 Dec |
|
Complications in treating chronic hepatitis B in patients with HIV. | 2005 Dec |
|
Adefovir-resistant hepatitis B can be associated with viral rebound and hepatic decompensation. | 2005 Dec |
|
Gateways to clinical trials. | 2005 Jan-Feb |
|
FDA notifications. Entecavir is approved for chronic hepatitis B infection in adults. | 2005 Jul |
|
Chronic hepatitis B--treatment with nucleoside analogues. | 2005 Jul |
|
Entecavir. | 2005 Jul |
|
[A study of the dosage and efficacy of entecavir for treating hepatitis B virus]. | 2005 Jul |
|
Treatment of chronic hepatitis B. | 2005 Jul |
|
New treatment for chronic hepatitis B. | 2005 Jul-Aug |
|
Clinical course of patients with chronic hepatitis B with viral breakthrough during long-term lamivudine treatment. | 2005 Jun |
|
Management of patients co-infected with hepatitis B virus and HIV. | 2005 Jun |
|
Susceptibility to antivirals of a human HBV strain with mutations conferring resistance to both lamivudine and adefovir. | 2005 Jun |
|
Entecavir (Baraclude) for chronic hepatitis B. | 2005 Jun 6 |
|
Current and future treatment of chronic hepatitis B. | 2005 Mar |
|
[Treatment of chronic hepatitis B]. | 2005 Mar 31 |
|
Gateways to clinical trials. | 2005 May |
|
New drugs and dosage forms. | 2005 May 1 |
|
New drugs: entecavir, ibandronate sodium, and pegaptanib sodium. | 2005 May-Jun |
|
Gateways to clinical trials. | 2005 Nov |
|
A review of entecavir in the treatment of chronic hepatitis B infection. | 2005 Nov |
|
A dose-ranging study of the efficacy and tolerability of entecavir in Lamivudine-refractory chronic hepatitis B patients. | 2005 Oct |
|
Clevudine for the treatment of chronic hepatitis B virus infection. | 2005 Oct |
|
Natural history and treatment of hepatitis B virus and hepatitis C virus coinfection. | 2005 Sep 13 |
|
[New aspect in the treatment of chronic hepatis B]. | 2005 Sep 7 |
|
Optimizing management strategies in special patient populations. | 2006 |
|
Looking to the future: new agents for chronic hepatitis B. | 2006 |
|
Therapeutic options for chronic hepatitis B: considerations and controversies. | 2006 |
|
Introduction to chronic hepatitis B infection. | 2006 |
|
Emerging therapeutics for chronic hepatitis B. | 2006 |
|
Treatment algorithm for chronic hepatitis B in HIV-infected patients. | 2006 |
|
Cellular and virological mechanisms of HBV drug resistance. | 2006 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.drugs.com/monograph/entecavir.html
Nucleoside-naive Individuals
Oral 0.5 mg once daily.
Lamivudine-refractory HBV or known lamivudine- or telbivudine-associated resistance mutations
Oral 1 mg once daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=18330958
Dendritic cells (DCs) derived from chronic hepatitis B (CHB) patients were treated with 0.05 ug/mL of Entecavir.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 02:33:48 UTC 2021
by
admin
on
Sat Jun 26 02:33:48 UTC 2021
|
Record UNII |
92A92XBK4S
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
92A92XBK4S
Created by
admin on Sat Jun 26 02:33:48 UTC 2021 , Edited by admin on Sat Jun 26 02:33:48 UTC 2021
|
PRIMARY | |||
|
911138-73-3
Created by
admin on Sat Jun 26 02:33:48 UTC 2021 , Edited by admin on Sat Jun 26 02:33:48 UTC 2021
|
PRIMARY | |||
|
135449303
Created by
admin on Sat Jun 26 02:33:48 UTC 2021 , Edited by admin on Sat Jun 26 02:33:48 UTC 2021
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |