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Compound Detail

CHEMBL922

ADEFOVIR DIPIVOXIL
💊 Approved Drug
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💊 Approved Drug
CC(C)(C)C(=O)OCOP(=O)(COCCn1cnc2c(N)ncnc21)OCOC(=O)C(C)(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL922
Name ADEFOVIR DIPIVOXIL
Phase Approved
Structure Type MOL
InChI Key WOZSCQDILHKSGG-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1162433

Known Names

Adefovir di(pivaloyloxymethyl) ester Adefovir dipivoxil Adefovir pivoxil GS-0840 Hepsera
18
Targets
63
Activities
3
Assay Types
22
PK Parameters
20
Publications
5
Known Names
6
Indications
1
Mechanisms

Molecular Properties

501.5
MW (Da)
2.70
ALogP
13
HBA
1
HBD
167.0
PSA (Ų)
0.21
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2002
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -vir
USAN Year 1996

Extended Properties

Molecular Formula C20H32N5O8P
MW 501.48
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness -0.33

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA polymerase/reverse transcriptase inhibitor INHIBITOR DNA polymerase/reverse transcriptase ✓ ✓

Indications

Hepatitis B, Chronic Hepatitis B, Chronic Virus Diseases Cytomegalovirus Infections HIV Infections Hepatitis, Chronic

ATC Classification

J05AF08
adefovir dipivoxil
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
metabolic toxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
nephrotoxicity
Country: United States

Activity Summary

EC50 44 meas. best 7.4
IC50 16 meas. best 7.22
Ki 3 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CEM-SS
CHEMBL614548
 EC50 7.4 7.4 40.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 7.35 7.05 45.0 2
Unchecked
CHEMBL612545
 IC50 7.22 6.612 60.8 5
Human immunodeficiency virus 2
CHEMBL380
 EC50 7.21 7.165 62.0 2
MT4
CHEMBL388
 EC50 7.1 7.1 80.0 1
Unchecked
CHEMBL612545
 Ki 7.0 7.0 100.0 1
Human alphaherpesvirus 2
CHEMBL370
 EC50 6.7 6.7 200.0 1
Human alphaherpesvirus 1
CHEMBL377
 EC50 6.7 6.7 200.0 2
Hepatitis B virus
CHEMBL613497
 IC50 6.48 6.3467 330.0 3
Vero
CHEMBL391
 IC50 6.22 6.22 600.0 1
BK polyomavirus
CHEMBL4888480
 EC50 6.16 6.16 700.0 1
Hepatitis B virus
CHEMBL613497
 EC50 6.08 5.1459 830.0 29
Vero
CHEMBL391
 EC50 6.06 6.0 870.0 2
MRC5
CHEMBL614181
 EC50 6.04 5.975 910.0 2
DNA polymerase subunit gamma-1
CHEMBL2732
 Ki 6.01 6.01 970.0 1
DNA polymerase alpha catalytic subunit
CHEMBL1828
 Ki 5.93 5.93 1180.0 1
Vaccinia virus
CHEMBL613493
 EC50 5.4 5.4 4000.0 1
Vaccinia virus
CHEMBL613493
 IC50 5.29 5.29 5100.0 1
Cowpox virus
CHEMBL612672
 IC50 4.89 4.89 13000.0 1
Solute carrier family 22 member 6
CHEMBL1641347
 IC50 4.87 4.87 13500.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.43 4.43 37300.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.34 4.34 46000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 383.63 ng.hr.mL-1 Homo sapiens
AUC 1655.22 ng.hr.mL-1 Rattus norvegicus
CL 60.4 L/hr Rattus norvegicus
Cmax 1222561.22 nM Rattus norvegicus
F 17.3 % Rattus norvegicus
MRT 5.676 hr Rattus norvegicus
T1/2 5.0 hr -
T1/2 5.0 hr -
T1/2 0.75 hr Homo sapiens
T1/2 0.75 hr Homo sapiens
T1/2 0.52 hr Rattus norvegicus
T1/2 7.0 hr -
T1/2 1.0 hr -
T1/2 1.0 hr -
T1/2 11.0 hr Homo sapiens
T1/2 11.0 hr Homo sapiens
T1/2 31.0 hr -
T1/2 55.0 hr -
T1/2 48.0 hr -
T1/2 72.0 hr -
T1/2 1.762 hr Rattus norvegicus
Vd 153.13 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CEM-SS EC50 = 40.0 nM 7.4 Compound was tested for antiviral activity against the CEM-SS cell lines infecte... 8960556
Human immunodeficiency virus 1 EC50 = 45.0 nM 7.35 Antiviral activity against wild type HIV-1 3B infected in human CEM cells assess... 23603046
Unchecked IC50 = 60.8 nM 7.22 PubChem BioAssay. Increased HeLa cells in S-phase-IC50. (Class of assay: confi... -
Human immunodeficiency virus 2 EC50 = 62.0 nM 7.21 Antiviral activity against wild type HIV-2 ROD infected in human CEM cells asses... 23603046
Human immunodeficiency virus 2 EC50 = 75.0 nM 7.12 Antiviral potency against HIV2 in CEM/O cells 16335932
MT4 EC50 = 80.0 nM 7.1 Compound was tested for antiviral activity against the MT-4 cell lines infected ... 8960556
Unchecked Ki = 100.0 nM 7.0 Binding affinity to Hepatitis B virus DNA polymerase assessed as inhibition cons... 37922830
Unchecked IC50 = 134.0 nM 6.87 PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator... -
Human immunodeficiency virus 1 EC50 = 180.0 nM 6.75 Antiviral potency against HIV1 in CEM/O cells 16335932
Human alphaherpesvirus 2 EC50 = 200.0 nM 6.7 Antiviral activity against Human simplex virus 2 G infected in human HEL cells a... 23603046
Human alphaherpesvirus 1 EC50 = 200.0 nM 6.7 Antiviral activity against thymidine kinase-deficient Human simplex virus 1 KOS ... 23603046
Human alphaherpesvirus 1 EC50 = 200.0 nM 6.7 Antiviral activity against Human simplex virus 1 KOS infected in human HEL cells... 23603046
Hepatitis B virus IC50 = 330.0 nM 6.48 Antiviral activity against Hepatitis B virus infected HepG2(2.2.15) cells assess... 19889538
Unchecked IC50 = 387.4 nM 6.41 PubChem BioAssay. alkaline phosphatase stimulation in WNT3A conditioned C2C12 ce... -
Unchecked IC50 = 391.3 nM 6.41 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Hepatitis B virus IC50 = 480.0 nM 6.32 Antiviral activity against Hepatitis B virus infected human HepG2(2.2.15) cells ... -
Hepatitis B virus IC50 = 580.0 nM 6.24 Antiviral activity against Hepatitis B virus infected human HepG2(2.2.15) cells ... -
Vero IC50 = 600.0 nM 6.22 Concentration that reduced plaque formation by 50% was measured in HSV-2 infecte... 8021925
BK polyomavirus EC50 = 700.0 nM 6.16 Antimicrobial activity against BK polyomavirus ATCC VR837 infected in human WI38... 18285481
Unchecked IC50 = 704.3 nM 6.15 PubChem BioAssay. nuclear beta catenin stimulation in WNT3A conditioned C2C12 ce... -

Literature References

PubMed DOI Target Context # Activities
18676881 10.1128/aac.00654-08 Woodchuck hepatitis virus 27
17371827 10.1128/aac.01440-06 Hepatitis B virus 26
31301948 10.1016/j.bmc.2019.07.012 HK-2 15
19398648 10.1128/aac.00114-09 Hepatitis B virus 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
17984230 10.1128/aac.00467-07 PBMC 13
20117930 10.1016/j.bmcl.2010.01.010 Hepatitis B virus 12
18676881 10.1128/aac.00654-08 Marmota monax 9
31301948 10.1016/j.bmc.2019.07.012 ADMET 9
23603046 10.1016/j.ejmech.2013.02.039 No relevant target 6
22305613 10.1016/j.ejmech.2012.01.013 ADMET 5
- 10.1007/s00044-011-9616-2 Duck hepatitis B virus 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
31301948 10.1016/j.bmc.2019.07.012 Hepatic sodium/bile acid cotransporter 4
8960556 10.1021/jm960289o ADMET 4
- 10.1007/s00044-011-9616-2 Hepatitis B virus 4
17984230 10.1128/aac.00467-07 Homo sapiens 4
20014752 10.1021/tx900326k Hepatotoxicity 3
8960556 10.1021/jm960289o MRC5 3
8960556 10.1021/jm960289o Vero 3

Data from ChEMBL 36 via Core Engine