ADEFOVIR DIPIVOXIL

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC J05AF08
UNII U6Q8Z01514
EPA CompTox DTXSID5046487

Structure

InChI Key WOZSCQDILHKSGG-UHFFFAOYSA-N
Smiles CC(C)(C)C(=O)OCOP(=O)(COCCn1cnc2c(N)ncnc21)OCOC(=O)C(C)(C)C
InChI
InChI=1S/C20H32N5O8P/c1-19(2,3)17(26)30-11-32-34(28,33-12-31-18(27)20(4,5)6)13-29-8-7-25-10-24-14-15(21)22-9-23-16(14)25/h9-10H,7-8,11-13H2,1-6H3,(H2,21,22,23)

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H32N5O8P
Molecular Weight 501.48
AlogP 2.7
Hydrogen Bond Acceptor 13.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 11.0
Polar Surface Area 166.98
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 34.0

Bioactivity

Mechanism of Action Action Reference
DNA polymerase/reverse transcriptase inhibitor INHIBITOR PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 13500 - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 46000 - - -
Assay Description Organism Bioactivity Reference
Compound was tested for antiviral activity against the CEM-SS cell lines infected with HIV-1. Homo sapiens 40.0 nM
Compound was tested for antiviral activity against the MT-4 cell lines infected with HIV-1. Homo sapiens 80.0 nM
Compound was tested for antiviral activity against the MRC-5 cells infected with HSV-2. Homo sapiens 910.0 nM
Concentration that reduced plaque formation by 50% was measured in HSV-2 infected vero cells in vitro Chlorocebus sabaeus 600.0 nM
Compound was tested for antiviral activity against the Vero cells infected with HSV-1. Chlorocebus sabaeus 870.0 nM
Antiviral potency against HIV1 in CEM/O cells Human immunodeficiency virus 1 180.0 nM
Antiviral potency against HIV2 in CEM/O cells Human immunodeficiency virus 2 75.0 nM
Antiviral activity against Hepatitis B virus infected HepG2(2.2.15) cells assessed as inhibition of viral cytoplasmic DNA synthesis by real-time PCR Hepatitis B virus 330.0 nM
Antimicrobial activity against BK polyomavirus ATCC VR837 infected in human WI38 cells assessed as reduction in viral titer after 7 days by PCR analysis BK polyomavirus 700.0 nM
Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as inhibition of viral replication incubated for 2 days followed by wash out measured after 10 days by RT-PCR analysis Hepatitis B virus 960.0 nM
Antiviral activity against Hepatitis B virus infected human HepG2(2.2.15) cells assessed as viral DNA level after 9 days by southern blot analysis Hepatitis B virus 480.0 nM
Antiviral activity against Hepatitis B virus infected human HepG2(2.2.15) cells assessed as inhibition of viral DNA replication after 9 days by RT-PCR analysis Hepatitis B virus 580.0 nM
Antiviral activity against Human simplex virus 2 G infected in human HEL cells assessed as reduction of virus-induced cytopathicity measured at day 3 by microscopic analysis Human herpesvirus 2 strain G 200.0 nM
Antiviral activity against thymidine kinase-deficient Human simplex virus 1 KOS infected in human HEL cells assessed as reduction of virus-induced cytopathicity measured at day 3 by microscopic analysis Human herpesvirus 1 strain KOS 200.0 nM
Antiviral activity against Human simplex virus 1 KOS infected in human HEL cells assessed as reduction of virus-induced cytopathicity measured at day 3 by microscopic analysis Human herpesvirus 1 strain KOS 200.0 nM
Antiviral activity against wild type HIV-2 ROD infected in human CEM cells assessed as inhibition of syncytia formation after 4 days by microscopic analysis Human immunodeficiency virus type 2 (ISOLATE ROD) 62.0 nM
Antiviral activity against wild type HIV-1 3B infected in human CEM cells assessed as inhibition of syncytia formation after 4 days by microscopic analysis Human immunodeficiency virus 1 45.0 nM
Antiviral activity against wild type HBV transfected in human HuH7 cells assessed as reduction of viral DNA level after 7 days by qPCR analysis Hepatitis B virus 830.0 nM
PubChem BioAssay. nuclear beta catenin stimulation in WNT3A conditioned C2C12 cells-IC50. (Class of assay: confirmatory) None 704.3 nM
PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmatory) None 134.0 nM
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory) None 391.3 nM
PubChem BioAssay. Increased HeLa cells in S-phase-IC50. (Class of assay: confirmatory) None 60.8 nM
PubChem BioAssay. alkaline phosphatase stimulation in WNT3A conditioned C2C12 cells-IC50. (Class of assay: confirmatory) None 387.4 nM
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 -3.56 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 30.75 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -0.4186 %
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 0.24 % 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 0.49 % 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 0.24 % 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 0.49 %

Related Entries

Cross References

Resources Reference
ChEBI 31175
ChEMBL CHEMBL922
DrugBank DB00718
DrugCentral 88
FDA SRS U6Q8Z01514
Human Metabolome Database HMDB0014856
PharmGKB PA10005
PubChem 60871
SureChEMBL SCHEMBL29729
ZINC ZINC000003930376
CONTENTS