ENTECAVIR

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC J05AF10
UNII NNU2O4609D
EPA CompTox DTXSID4046446

Structure

InChI Key QDGZDCVAUDNJFG-FXQIFTODSA-N
Smiles C=C1[C@H](CO)[C@@H](O)C[C@@H]1n1cnc2c(=O)[nH]c(N)nc21
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H15N5O3
Molecular Weight 277.28
AlogP -0.83
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 2.0
Polar Surface Area 130.05
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 20.0

Bioactivity

Mechanism of Action Action Reference
DNA polymerase/reverse transcriptase inhibitor INHIBITOR DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Structural protein
0 - - - 23-98
Assay Description Organism Bioactivity Reference
Tested for the effective concentration required to inhibit HBV in HepG2.2.15 human liver cells Homo sapiens 3.0 nM
Inhibition of HBV replication with RT A200V substitution from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 7.6 nM
Inhibition of HBV replication with RT A200V substitution and M204I background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 33.0 nM
Inhibition of HBV replication with RT A200V substitution and L180M, M204I background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 10.2 nM
Inhibition of HBV replication with RT L80V substitution and L180M, M204V background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 11.0 nM
Inhibition of HBV replication with RT V27A substitution and L180M, M204V background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 10.0 %
Inhibition of HBV replication with RT I53F substitution and V173F, L180M, M204V background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 22.3 nM
Inhibition of HBV replication with RT S78T substitution from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 2.4 nM
Inhibition of HBV replication with RT L80I substitution and L180M, M204I background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 45.3 nM
Inhibition of HBV replication with RT K168E substitution and M204I background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 10.0 %
Inhibition of HBV replication with RT A181T substitution and V173L, L180M, M204V background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 14.2 nM
Inhibition of HBV replication with RT C188S substitution and L80I, L180T, M204V background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 31.2 nM
Inhibition of HBV replication with RT V224A substitution and V173L, L180M, M204V background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 10.0 %
Inhibition of HBV replication with RT L228P substitution and M204I background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 10.0 %
Inhibition of HBV replication with RT L229W substitution and L180M, M204V background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 32.9 nM
Inhibition of HBV replication with RT D263G substitution from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 5.8 nM
Inhibition of HBV replication with RT Q267Stop substitution and L180M, M204V background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 10.0 %
Inhibition of HBV replication with RT G295S substitution and L80I, M204I background from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 10.0 %
Inhibition of HBV replication with RT M309L substitution from Lamivudine refractory patient transfected into HepG2 cells Hepatitis B virus 4.0 nM
Inhibition of wild type HBV replication in Huh7 cells Hepatitis B virus 300.0 nM
Antiviral activity against wild type HBV assessed as inhibition of replication Hepatitis B virus 800.0 nM
Antiviral activity against adenofir-resistant HBV with reverse transcriptase N236T mutant assessed as inhibition of replication Hepatitis B virus 700.0 nM
Antiviral activity against wild type HBV genotype H assessed as inhibition of replication Hepatitis B virus 90.0 nM
Antiviral activity against wild type HBV genotype E assessed as inhibition of replication Hepatitis B virus 60.0 nM
Antiviral activity against lamivudine-adenofir-resistant HBV with reverse transcriptase V173L/L180M/A181V/N236T mutant Hepatitis B virus 500.0 nM
Antiviral activity against Hepatitis B virus Hepatitis B virus 4.0 nM
Antiviral activity against HIV1 subtype B-RF infected in 1 hr-pretreated human MT2 cells assessed as inhibition of multicycle replication measured on day 5 postinfection by RT SPA Human immunodeficiency virus 1 839.0 nM
Antiviral activity against HIV1 subtype B-SF-2 infected in 1 hr-pretreated human MT2 cells assessed as inhibition of multicycle replication measured on day 5 postinfection by RT SPA Human immunodeficiency virus 1 526.0 nM
Antiviral activity against HIV1 subtype B-3B infected in 1 hr-pretreated human MT2 cells assessed as inhibition of multicycle replication measured on day 5 postinfection by RT SPA Human immunodeficiency virus 1 81.0 nM
Antiviral activity against HIV1 subtype B-LAI infected in 1 hr-pretreated human MT2 cells assessed as inhibition of multicycle replication measured on day 5 postinfection by RT SPA Human immunodeficiency virus 1 71.0 nM
Antiviral activity against HIV1 subtype B-NL4-3 infected in 1 hr-pretreated human MT2 cells assessed as inhibition of multicycle replication measured on day 5 postinfection by RT SPA Human immunodeficiency virus 1 85.0 nM
Antiviral activity against HIV1 subtype B-ASM 034 infected in 1 hr-pretreated PBMC cells assessed as inhibition of p24 antigen production measured on day 5 postinfection by ELISA Human immunodeficiency virus 1 109.0 nM
Antiviral activity against HIV1 subtype B-92US076 infected in 1 hr-pretreated PBMC cells assessed as inhibition of p24 antigen production measured on day 5 postinfection by ELISA Human immunodeficiency virus 1 62.0 nM
Antiviral activity against HIV1 subtype B-ASM 044 infected in 1 hr-pretreated PBMC cells assessed as inhibition of p24 antigen production measured on day 5 postinfection by ELISA Human immunodeficiency virus 1 26.0 nM
Antiviral activity against 0.005 MOI wild type HIV1 NL4-3 infected in human MT2 cells measured after 5 days by RT SPA Human immunodeficiency virus 1 56.0 nM
Antiviral activity against 0.01 MOI wild type HIV1 NL4-3 infected in human MT2 cells measured after 5 days by RT SPA Human immunodeficiency virus 1 95.0 nM
Antiviral activity against 0.02 MOI wild type HIV1 NL4-3 infected in human MT2 cells measured after 5 days by RT SPA Human immunodeficiency virus 1 449.0 nM
Antiviral activity against 0.006 MOI HIV1 NL4-3 infected in human MT2 cells measured after 5 days by RT SPA Human immunodeficiency virus 1 151.0 nM
Antiviral activity against 0.006 MOI HIV1 NL4-3 infected in 1 hr-pretreated human MT2 cells measured after 5 days by RT SPA Human immunodeficiency virus 1 287.0 nM
Antiviral activity against 0.005 MOI HIV1 NL4-3 harboring wild type RT infected in human MT2 cells Human immunodeficiency virus 1 56.0 nM
Antiviral activity against HIV infected in CD4+ lymphocyte by fluorescence-activated cell sorter assay Human immunodeficiency virus 0.1 nM
Antiviral activity against wild type Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as inhibition of virus replication treated daily for 9 days by quantitative blot hybridization method Hepatitis B virus 8.0 nM
Antiviral activity against wild type Hepatitis B virus infected in human HuH7 cells Hepatitis B virus 8.0 nM
Antiviral activity against Hepatitis B virus in HepG2.CW cells assessed as inhibition of viral DNA replication at 1 uM after 9 days by real-time FQ-PCR analysis Hepatitis B virus 95.7 %
Antiviral activity against Hepatitis B virus in HepG2.2.15 cells assessed as inhibition of intracellular viral DNA replication at 0.1 uM after 3 days by real-time FQ-PCR analysis Hepatitis B virus 37.8 %
Antiviral activity against Hepatitis B virus in HepG2.2.15 cells assessed as inhibition of intracellular viral DNA replication at 0.1 uM after 6 days by real-time FQ-PCR analysis Hepatitis B virus 40.6 %
Antiviral activity against Hepatitis B virus in HepG2.2.15 cells assessed as inhibition of intracellular viral DNA replication at 0.1 uM after 9 days by real-time FQ-PCR analysis Hepatitis B virus 57.6 %
Antiviral activity against Hepatitis B virus in HepG2.2.15 cells assessed as inhibition of extracellular viral DNA replication at 0.1 uM after 3 days by real-time FQ-PCR analysis Hepatitis B virus 38.2 %
Antiviral activity against Hepatitis B virus in HepG2.2.15 cells assessed as inhibition of extracellular viral DNA replication at 0.1 uM after 6 days by real-time FQ-PCR analysis Hepatitis B virus 47.8 %
Antiviral activity against Hepatitis B virus in HepG2.2.15 cells assessed as inhibition of extracellular viral DNA replication at 0.1 uM after 9 days by real-time FQ-PCR analysis Hepatitis B virus 78.6 %
Antiviral activity against HBV ayw1 infected in human HepG2(2.2.15) cells assessed as reduction in viral replication by measuring extracellular viral DNA copy number after 6 days by real-time qPCR method Hepatitis B virus 10.0 nM
Antiviral activity against HBV ayw1 infected in human HepG2(2.2.15) cells assessed as reduction in viral replication by measuring intracellular viral DNA copy number after 6 days byr by real-time qPCR assay Hepatitis B virus 0.35 nM
Antiviral activity against HBV infected in human HepG2(2.2.15) cells assessed as inhibition of viral DNA replication at 10 uM after 72 hrs by RT-PCR method relative to control Hepatitis B virus 95.67 %
Antiviral activity against lamivudine/entecavir resistant HBV harboring reverse transcriptase L180M/M204V/T184L mutant infected in human HepG2(2.2.15) cells assessed as inhibition of viral DNA replication at 10 uM after 72 hrs by RT-PCR method relative to control Hepatitis B virus 17.9 %
Inhibition of hepatitis B virus capsid assembly infected in human HepG2.215 cells assessed as reduction in viral DNA replication measured on day 7 by real time PCR analysis Hepatitis B virus 0.24 nM
Antiviral activity against entecavir-resistant wild type hepatitis B virus infected in human Huh7 cells assessed as reduction in intracellular DNA levels measured on day 7 by real-time PCR analysis Hepatitis B virus 13.0 nM
Antiviral activity against entecavir-resistant wild type hepatitis B virus infected in human Huh7 cells assessed as reduction in secreted DNA levels measured on day 7 by real-time PCR analysis Hepatitis B virus 14.0 nM
Inhibition of capsid in HBV infected in human HepAD38 cells assessed as reduction in cccDNA formation by measuring reduction in HBe antigen secretion at 10 uM after 14 days by ELISA relative to control Hepatitis B virus 1.0 %
Antiviral activity against HBV infected in human HepAD38 cells assessed as reduction in extracellular viral DNA level by RT-PCR method Hepatitis B virus 0.7 nM
Antiviral activity against HBV infected in human HepAD38 cells assessed as reduction in intracellular viral DNA level by RT-PCR method Hepatitis B virus 0.1 nM
Antiviral activity against Hepatitis B virus infected in human dHepaRG cells assessed as reduction in HBsAg secretion after 10 mins by chemiluminescence immunoassay Hepatitis B virus 1.0 nM
Antiviral activity against Hepatitis B virus infected in human dHepaRG cells assessed as reduction in HBeAg secretion after 10 mins by chemiluminescence immunoassay Hepatitis B virus 1.0 nM
Antiviral activity against Hepatitis B virus infected in human dHepaRG cells assessed as reduction in extracellular viral DNA levels after 6 days by qPCR/TaqMan assay Hepatitis B virus 0.06 nM
Antiviral activity against HBV genotype D infected in human HepG2.2.15 cells assessed as reduction in viral DNA level after 7 days by RT-PCR assay HBV genotype D 3.8 nM
Inhibition of capsid protein in lamivudine/entecavir-resistant Hepatitis B virus harboring rtL180M/rtM204V/rt184L mutant infected in human HepG2.2.15 cells assessed as reduction in viral DNA level at 10 uM measured after 72 hrs by PCR analysis relative to control Hepatitis B virus 22.58 %
Inhibition of capsid protein in wild type Hepatitis B virus infected in human HepG2.2.15 cells assessed as reduction of viral DNA level at 10 uM measured after 72 hrs by PCR analysis relative to control Hepatitis B virus 98.07 %
Antiviral activity against HBV infected in human HepAD38 cells assessed as reduction in viral DNA levels incubated for 6 days by PCR analysis Hepatitis B virus 11.0 nM
Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as reduction in viral DNA levels incubated for 6 days by PCR analysis Hepatitis B virus 0.0022 nM
Antiviral activity against wild type HBV infected in human HepG2 2.2.15 cells assessed as inhibition of viral DNA replication at 10 uM measured after incubation of 72 hrs by RT-PCR analysis relative to control Hepatitis B virus 96.82 %
Antiviral activity against lamivudine/entecavir-resistant HBV rtL180M/rtM204V/rtT184L mutant infected in human HepG2 2.2.15 cells assessed as inhibition of viral DNA replication at 10 uM measured after incubation of 72 hrs by RT-PCR analysis relative to control Hepatitis B virus 20.71 %
Antiviral activity against Hepatitis B virus infected in human HePAD38 cells assessed as reduction in viral DNA replication incubated for 7 days by RT-PCR analysis Hepatitis B virus 0.6 nM
Antiviral activity against Hepatitis B virus infected in human HepG2.2.15.7 assessed as reduction in HBV DNA level incubated for 9 days media replaced every 3 days once with test compound by RT-PCR analysis Hepatitis B virus 0.18 nM
Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as inhibition of DNA replication at 10 uM supplemented with fresh medium containing compound every 2 days for 6 days by RT-PCR analysis relative to control Hepatitis B virus 96.9 %
Antiviral activity against lamivudine and entecavir-resistant HBV harboring rtL180 M/rtM204V/rtT184L mutant infected in human HepG2.2.15 cells assessed as inhibition of DNA replication at 10 uM supplemented with fresh medium containing compound every 2 days for 6 days by RT-PCR analysis relative to control Hepatitis B virus 18.92 %

Cross References

Resources Reference
ChEBI 473990
ChEMBL CHEMBL713
DrugBank DB00442
DrugCentral 1019
FDA SRS NNU2O4609D
Human Metabolome Database HMDB0014585
PharmGKB PA164784025
PubChem 135526609
SureChEMBL SCHEMBL28648
ZINC ZINC000003802690
CONTENTS