TENOFOVIR

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Mixture
UNII W4HFE001U5
EPA CompTox DTXSID9040132

Structure

InChI Key SGOIRFVFHAKUTI-ZCFIWIBFSA-N
Smiles C[C@H](Cn1cnc2c(N)ncnc21)OCP(=O)(O)O
InChI
InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H14N5O4P
Molecular Weight 287.22
AlogP -0.05
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 5.0
Polar Surface Area 136.38
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 19.0

Bioactivity

Mechanism of Action Action Reference
DNA polymerase/reverse transcriptase inhibitor INHIBITOR PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 380-380 3200 - -
Structural protein
242 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 18
Assay Description Organism Bioactivity Reference
Antiviral activity against HIV1 in MAGI-CCR5 cells Human immunodeficiency virus 1 350.0 nM
Inhibition of HIV1 reverse transcriptase Human immunodeficiency virus 1 380.0 nM
Inhibition of wild type HIV reverse transcriptase Human immunodeficiency virus 380.0 nM
Inhibition of wild type HIV 3B reverse transcriptase in MT2 cells Human immunodeficiency virus 1 380.0 nM
Antiviral activity against R5-HIV1Ba-L assessed as inhibition of p24 Gag protein production in human PHA-PBMC by ELISA Human immunodeficiency virus 1 32.0 nM
Antiviral activity against R5-HIV1MDR/MM assessed as inhibition of p24 Gag protein production in human PHA-PBMC by ELISA Human immunodeficiency virus 1 82.0 nM
Antiviral activity against X4-HIV1 NL4-3 assessed as inhibition of p24 Gag protein production in human MT4 cells by MTT assay Human immunodeficiency virus 1 0.0 nM
Antiviral activity against R5-HIV1MDR/C assessed as inhibition of p24 Gag protein production in human PHA-PBMC by ELISA Human immunodeficiency virus 1 47.0 nM
Antiviral activity against R5-HIV1MDR/G assessed as inhibition of p24 Gag protein production in human PHA-PBMC by ELISA Human immunodeficiency virus 1 87.0 nM
Inhibition of murine sarcoma virus-induced transformation of mouse embryo fibroblast C3H/3T3 cells after 6 days Moloney murine leukemia virus 230.0 nM
Inhibition on HIV1 reverse transcriptase p66/p51 Human immunodeficiency virus 1 380.0 nM
Antiviral activity against HIV1 LAI in human MT2 cells assessed as inhibition of p24 antigen production by ELISA Human immunodeficiency virus 1 650.0 nM
Antiviral activity against HIV1 3B infected in human MT2 cells assessed as inhibition of virus-induced cytopathic effect after 5 days by XTT assay Human immunodeficiency virus 1 13.0 nM
Antiviral activity against HIV1 NL 4-3 expressing wild type reverse transcriptase infected in human PBMC by ELISA Human immunodeficiency virus 1 300.0 nM
Selectivity ratio of EC50 for HIV1 7324-1 harboring reverse transcriptase 41L/67N/69N/70R/215F/219E mutant gene infected in human PBMC to EC50 for HIV1 NL 4-3 expressing wild type reverse transcriptase infected in human PBMC Human immunodeficiency virus 1 22.0 nM
Selectivity ratio of EC50 for HIV1 4755-5 harboring reverse transcriptase 41L/44D/67N/69D/118I/210W/215Y/184V mutant gene infected in human PBMC to EC50 for HIV1 NL 4-3 expressing wild type reverse transcriptase infected in human PBMC Human immunodeficiency virus 1 18.0 nM
Selectivity ratio of EC50 for HIV1 7303-3 harboring reverse transcriptase 41L/44D/67N/69D/118I/210W/215Y mutant gene infected in human PBMC to EC50 for HIV1 NL 4-3 expressing wild type reverse transcriptase infected in human PBMC Human immunodeficiency virus 1 28.0 nM
Selectivity ratio of EC50 for HIV1 1617-1 harboring reverse transcriptase 69K/70G/75I/77L/116Y/151M/184V mutant gene infected in human PBMC to EC50 for HIV1 NL 4-3 expressing wild type reverse transcriptase infected in human PBMC Human immunodeficiency virus 1 22.0 nM
Selectivity ratio of EC50 for HIV1 52534-2 harboring reverse transcriptase 41L//74V/210W/215Y/184V/69SSS mutant gene infected in human PBMC to EC50 for HIV1 NL 4-3 expressing wild type reverse transcriptase infected in human PBMC Human immunodeficiency virus 1 22.0 nM
Selectivity ratio of EC50 for HIV1 71361-1 harboring reverse transcriptase 65R mutant gene infected in human PBMC to EC50 for HIV1 NL 4-3 expressing wild type reverse transcriptase infected in human PBMC Human immunodeficiency virus 1 27.0 nM
Selectivity ratio of EC50 for HIV1 8415-2 harboring reverse transcriptase 65R/184V mutant gene infected in human PBMC to EC50 for HIV1 NL 4-3 expressing wild type reverse transcriptase infected in human PBMC Human immunodeficiency virus 1 3.3 nM
Antiviral activity against HIV1 isolate 056 expressing wild type reverse transcriptase gene by phenosense assay Human immunodeficiency virus 1 610.0 nM
Antiviral activity against HIV1 isolate 057 expressing wild type reverse transcriptase gene by phenosense assay Human immunodeficiency virus 1 650.0 nM
Antiviral activity against HIV1 isolate 066 harboring reverse transcriptase 184V mutant gene by phenosense assay Human immunodeficiency virus 1 530.0 nM
Antiviral activity against HIV1 isolate 071 harboring reverse transcriptase 65R/S68N/184V mutant gene by phenosense assay Human immunodeficiency virus 1 940.0 nM
Antiviral activity against HIV1 isolate 153 harboring reverse transcriptase L74V mutant gene by phenosense assay Human immunodeficiency virus 1 480.0 nM
Antiviral activity against HIV1 isolate 157 harboring reverse transcriptase L74V/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 230.0 nM
Antiviral activity against HIV1 isolate 166 harboring reverse transcriptase L74V mutant gene obtained as site-directed mutant of NL4-3 by phenosense assay Human immunodeficiency virus 1 540.0 nM
Antiviral activity against HIV1 isolate 174 harboring reverse transcriptase M184V mutant gene obtained as site-directed mutant of NL4-3 by phenosense assay Human immunodeficiency virus 1 410.0 nM
Antiviral activity against HIV1 isolate 188 harboring reverse transcriptase T215Y/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 620.0 nM
Antiviral activity against HIV1 isolate 203 harboring reverse transcriptase M41L/L210W/T215Y/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 750.0 nM
Antiviral activity against HIV1 isolate 204 harboring reverse transcriptase M41L/L210W/T215Y/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 790.0 nM
Antiviral activity against HIV1 isolate 211 harboring reverse transcriptase D67N/K70R/T215F/K219E/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 700.0 nM
Antiviral activity against HIV1 isolate 215 harboring reverse transcriptase D67N/K70E mutant gene by phenosense assay Human immunodeficiency virus 1 740.0 nM
Antiviral activity against HIV1 isolate 217 harboring reverse transcriptase D67N/K70E/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 500.0 nM
Antiviral activity against HIV1 isolate 220 harboring reverse transcriptase K70E/M184V mutant gene by phenosense assay Human immunodeficiency virus 1 470.0 nM
Antiviral activity against HBV infected in human HepG 2.215 cells assessed as inhibition of DNA replication by RT-PCR analysis Hepatitis B virus 540.0 nM
Antiviral activity against R5 tropic HIV1 YU.2 infected in human PBMC assessed as inhibition of p24 antigen production after 2 hrs by ELISA Human immunodeficiency virus 1 884.24 nM
Antiviral activity against HIV1 isolate 8415-2 harboring reverse transcriptase K65R mutant co-expressing M184V mutant infected in human TZM-b1 cells after 2 hrs by luciferase assays Human immunodeficiency virus 1 820.0 nM
Antiviral activity against 125 TCID50 wild type HIV1 LAI infected in human H9 cells assessed as reduction in viral replication measured on day 7 post infection by reverse transcriptase activity Human immunodeficiency virus 1 230.0 nM
Antiviral activity against HIV1 clade B isolate 2101 infected in human H9 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 240.0 nM
Antiviral activity against HIV1 clade B isolate 1722 infected in human H9 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 690.0 nM
Antiviral activity against HIV1 clade C isolate 2914 infected in human H9 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 340.0 nM
Antiviral activity against HIV1 clade C isolate 4110 infected in human H9 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 830.0 nM
Antiviral activity against HIV1 clade D isolate 1649 infected in human H9 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 100.0 nM
Antiviral activity against HIV1 clade A/E isolate 2165 infected in human H9 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 510.0 nM
Antiviral activity against HIV1 clade F isolate 2338 infected in human H9 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 40.0 nM
Antiviral activity against HIV1 clade G isolate 3187 infected in human H9 cells assessed as inhibition of viral replication Human immunodeficiency virus 1 150.0 nM
Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as reduction in viral DNA replication Hepatitis B virus 890.0 nM
Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as inhibition of viral DNA replication by RT-PCR analysis Hepatitis B virus 770.0 nM
Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as inhibition of viral DNA replication by PCR analysis Hepatitis B virus 680.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 18.4 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 33.6 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 23.3 %
Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as inhibition of viral DNA replication Hepatitis B virus 490.0 nM
Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as inhibition of DNA replication Hepatitis B virus 710.0 nM
Inhibition of HBV DNA replication in HepG2(2.2.15) cells exposed to fresh medium supplemented with compound every other day for additional 5 days by real-time PCR-fluorescent probing method Hepatitis B virus 500.0 nM
Antiviral activity against CXCR4-tropic HIV-1 NL4-3 infected in human PHA-stimulated PBMC assessed as inhibition of viral replication by measuring reduction in p24 antigen production preincubated with cells for 30 mins followed by viral infection measured on day 10 post infection in presence of IL-2 by ELISA Human immunodeficiency virus 1 380.0 nM
Antiviral activity against tenofovir-resistant CXCR4-tropic HIV-1 NL4-3 harboring reverse transcriptase K65R mutant infected in human MT4 cells assessed as inhibition of viral replication inhibition of virus-induced cytopathic effect after 6 days by XTT dye based assay Human immunodeficiency virus 1 100.0 nM
Antiviral activity against CXCR4-tropic HIV-1 NL4-3 infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect after 6 days by XTT dye based assay Human immunodeficiency virus 1 60.0 nM
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 241.5 nM
Antiviral activity against HSV unidentified herpesvirus 105.0 ug.mL-1
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -14.56 %
Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of viral replication by measuring reverse transcriptase activity in cell supernatant preincubated with cells followed by viral infection measured after 7 days by radioactive incorporation polymerization assay Human immunodeficiency virus 1 319.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 18.78 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 34.82 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.02 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.07 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.02 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.07 %
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 10.0 nM
Antiviral activity against HBV infected in human HepG2.A64 cells containing reverse transcriptase L180M/T184L/M204V mutant assessed as reduction in viral replication incubated for 6 days by PCR analysis Hepatitis B virus 840.0 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 0.064 nM
Antiviral activity against HIV1 infected in human PBMC assessed as reduction in viral replication incubated for 7 days by radioactive incorporation polymerization assay based reverse transcriptase activity detection method Human immunodeficiency virus 1 320.0 nM

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Romania
Slovakia
South Africa

Cross References

Resources Reference
ChEBI 63625
ChEMBL CHEMBL483
DrugBank DB14126
DrugCentral 2592
FDA SRS W4HFE001U5
Human Metabolome Database HMDB0014445
Guide to Pharmacology 10948
PDB TFO
PharmGKB PA10204
PubChem 21146529
SureChEMBL SCHEMBL39724
ZINC ZINC000001543475
ChEBI 63716
ChEMBL CHEMBL3989702
FDA SRS 99YXE507IL
Guide to Pharmacology 10948
PubChem 21146529
SureChEMBL SCHEMBL3133902
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