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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2311221 Sources: http://www.drugbank.ca/drugs/DB00442 |
0.0040000000000000001 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 Date1112054400000 |
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 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| 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 |
||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| likely | ||||
| no | ||||
| no | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 12, 13, 14 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Hepatitis B in children: natural history and therapy]. | 2001 |
|
| Antiviral drugs: current state of the art. | 2001 Aug |
|
| The polymerase L528M mutation cooperates with nucleotide binding-site mutations, increasing hepatitis B virus replication and drug resistance. | 2001 Feb |
|
| Safety and efficacy of oral entecavir given for 28 days in patients with chronic hepatitis B virus infection. | 2001 Sep |
|
| Management of patients with chronic hepatitis B. | 2002 Apr |
|
| Efficacies of entecavir against lamivudine-resistant hepatitis B virus replication and recombinant polymerases in vitro. | 2002 Aug |
|
| Entecavir is superior to lamivudine in reducing hepatitis B virus DNA in patients with chronic hepatitis B infection. | 2002 Dec |
|
| Therapy of chronic hepatitis B: current challenges and opportunities. | 2002 Nov |
|
| Gateways to clinical trials. | 2002 Oct |
|
| [Nucleoside analogues resistance in the treatment of chronic hepatitis B virus infection]. | 2003 Dec |
|
| Management of patients with decompensated HBV cirrhosis. | 2003 Feb |
|
| Current and future antiviral agents for chronic hepatitis B. | 2003 Mar |
|
| Gateways to clinical trials. | 2003 Oct |
|
| Gateways to clinical trials. | 2003 Sep |
|
| New treatment of chronic hepatitis B. | 2004 |
|
| Molecular virology of hepatitis B virus. | 2004 |
|
| [Advances in the treatment of acute hepatitis B]. | 2004 Aug |
|
| Management of hepatitis B patients with antiviral resistance. | 2004 Dec |
|
| Hepatitis B virus epidemiology, disease burden, treatment, and current and emerging prevention and control measures. | 2004 Mar |
|
| 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 |
|
| Clinical emergence of entecavir-resistant hepatitis B virus requires additional substitutions in virus already resistant to Lamivudine. | 2004 Sep |
|
| US approves new HBV drug. | 2005 Apr |
|
| Chronic hepatitis B--treatment with nucleoside analogues. | 2005 Jul |
|
| [A study of the dosage and efficacy of entecavir for treating hepatitis B virus]. | 2005 Jul |
|
| 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 |
|
| Gateways to clinical trials. | 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 |
|
| Therapeutic options for chronic hepatitis B: considerations and controversies. | 2006 |
|
| Introduction to chronic hepatitis B infection. | 2006 |
|
| Emerging therapeutics for chronic hepatitis B. | 2006 |
Patents
| Substance Class |
Chemical
Created
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admin
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Edited
Sat Jun 26 02:33:48 UTC 2021
by
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Sat Jun 26 02:33:48 UTC 2021
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| Record UNII |
92A92XBK4S
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| Record Status |
Validated (UNII)
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| Record Version |
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