Adefovir Dipivoxil
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Also known as Adefovir di(pivaloyloxymethyl) esterAdefovir pivoxilGS-0840HepseraSID26758046SID174007317SID170464742SID144205796ADEFOVIR DIPIVOXIL (PREVEON, HEPSERA)Adefovir dipivoxilÊAdefovir Dipivoxil (PreveonHepsera)Adefovir dipivoxilÂ
Summary
Adefovir Dipivoxil (CHEMBL922) is an approved small-molecule prodrug (ATC J05AF08); indicated across 6 conditions including hepatitis b virus infection and chronic hepatitis b virus infection.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J05AF08
- Indications: 6 conditions
- Clinical trials: 53
- Chemistry: 501.5 Da · C20H32N5O8P
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL922 |
| Name | Adefovir Dipivoxil |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 60871 |
| ChEBI | CHEBI:31175 |
| ATC | J05AF08 |
| Molecular formula | C20H32N5O8P |
| Molecular weight | 501.5 |
| InChIKey | WOZSCQDILHKSGG-UHFFFAOYSA-N |
SMILES: CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N=CN=C21)N)OCOC(=O)C(C)(C)C
IUPAC name: [2-(6-aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate
ChEBI definition: An organic phosphonate that is the dipivoxil ester of adefovir. A prodrug for adefovir, an HIV-1 reverse transcriptase inhibitor, adefovir pivoxil is used to treat chronic hepatitis B viral infection.
Pharmacological roles (ChEBI): prodrug, antiviral drug, DNA synthesis inhibitor, HIV-1 reverse transcriptase inhibitor, nephrotoxic agent.
Also known as: Adefovir di(pivaloyloxymethyl) ester, Adefovir dipivoxil, Adefovir pivoxil, GS-0840, Hepsera, Adefovir Dipivoxil, SID26758046, ADEFOVIR DIPIVOXIL, adefovir dipivoxil, SID174007317, SID170464742, SID144205796
Parent form; salt/anhydrous children: CHEMBL537884
Patent coverage: 7,756 distinct patent families (27,632 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 27,149 (98%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: 4’-phosphopantetheinyl transferase ffp, Solute carrier family 22 member 6, DNA polymerase alpha catalytic subunit, DNA polymerase subunit gamma-1, Prolyl endopeptidase FAP, Bile salt export pump.
Bioactivity
ChEMBL activities: 4 potent at pChembl ≥ 5 of 8 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| FAP | 7.02 | IC50 | 96 | nM | CHEMBL_ACT_29108092 |
| FAP | 6.77 | Ki | 170 | nM | CHEMBL_ACT_29108079 |
| POLG | 6.01 | Ki | 970 | nM | CHEMBL_ACT_25952706 |
| POLA1 | 5.93 | Ki | 1180 | nM | CHEMBL_ACT_25952705 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
6 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| hepatitis B virus infection | 4 | MONDO:0005344 | EFO:0004197 |
| chronic hepatitis B virus infection | 4 | MONDO:0005366 | EFO:0004239 |
| viral infectious disease | 4 | MONDO:0005108 | EFO:0000763 |
| HIV infectious disease | 3 | MONDO:0005109 | EFO:0000764 |
| cytomegalovirus infection | 3 | MONDO:0005132 | EFO:0001062 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 53.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 14 |
| PHASE2 | 13 |
| Not specified | 11 |
| PHASE3 | 7 |
| PHASE1 | 6 |
| PHASE1/PHASE2 | 2 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00187746 | PHASE4 | WITHDRAWN | Effect of Age on the Renal Clearance of Adefovir |
| NCT00230477 | PHASE4 | COMPLETED | Hepsera Versus Hepsera Plus Lamivudine for Treatment of Chronic Hepatitis B in Patients With Normal ALT |
| NCT00307242 | PHASE4 | COMPLETED | Study Comparing the Safety of Switching From Lamivudine to Adefovir Dipivoxil Versus Overlapping Lamivudine and Adefovir Before Adefovir Dipivoxil Monotherapy in Patients With Chronic Hepatitis B |
| NCT00324961 | PHASE4 | COMPLETED | Adefovir Dipivoxil Tablets (10mg) In Chinese Subjects With HBe Antigen Negative Chronic Hepatitis B |
| NCT00347009 | PHASE4 | COMPLETED | Adefovir Dipivoxil For The Treatment Of Patients With Chronic Hepatitis B Related Advanced Fibrosis Or Cirrhosis |
| NCT00403585 | PHASE4 | COMPLETED | Study of Adefovir Dipivoxil for Korean Patients With Chronic Hepatitis B(CHB) Who Have Completed ADF 103814 |
| NCT00441974 | PHASE4 | COMPLETED | Adefovir Dipivoxil For The Treatment Of Chinese Compensated Chronic Hepatitis B(CHB)Patients |
| NCT00606099 | PHASE4 | WITHDRAWN | Efficacy and Safety of Telbivudine in Patients With Chronic Hepatitis B |
| NCT00641082 | PHASE4 | COMPLETED | A Double-Blind Randomized Clinical Trial Comparing the Safety and Antiviral Activity of 48-week Clevudine and Adefovir Dipivoxil in HBeAg(-) Chronic Hepatitis B With Compensated Liver Function |
| NCT00810524 | PHASE4 | UNKNOWN | Influence of Antiviral Treatment to the Long-Term Prognosis of Patients With Chronic HBV Infection |
| NCT01436539 | PHASE4 | UNKNOWN | Study of Effects and Safety Between Adefovir Dipivoxil Plus Polyene Phosphatidylcholine Versus Adefovir Dipivoxil Alone in Chronic Hepatitis B Patients |
| NCT01521975 | PHASE4 | COMPLETED | A Two-year Study of Telbivudine in HBeAg Negative Hepatitis |
| NCT02598063 | PHASE4 | COMPLETED | A Study to Evaluate Efficacy and Safety of Peginterferon Alfa-2a (Pegasys) and Adeforvir Dipivoxil (ADV) in Participants With Lamivudine-Resistant Hepatitis B e Antigen (HBeAg)-Positive Chronic Hepatitis B |
| NCT02826070 | PHASE4 | UNKNOWN | EFFORT Further Extension Study |
| NCT00001082 | PHASE3 | COMPLETED | The Safety and Effectiveness of Adefovir Dipivoxil in the Treatment of HIV-Infected Patients |
| NCT00002220 | PHASE3 | COMPLETED | Indinavir Plus Efavirenz Plus Adefovir Dipivoxil in HIV-Infected Patients Who Have Not Had Success With Nelfinavir |
| NCT00023153 | PHASE3 | COMPLETED | Lamivudine and Adefovir to Treat Chronic Hepatitis B Infection in People With and Without HIV Infection |
| NCT00115245 | PHASE3 | COMPLETED | Telbivudine Versus Adefovir Dipivoxil in Adults With HBegAg-Positive, Compensated Chronic Hepatitis B |
| NCT00376259 | PHASE3 | TERMINATED | Study of Combination Therapy With LdT Plus Adefovir Versus Adefovir Alone |
| NCT00661076 | PHASE3 | COMPLETED | ADVANCE Study: A Study of PEGASYS (Peginterferon Alfa-2a (40KD)) + Adefovir Dipivoxil in Patients With Hbe(-) Chronic Hepatitis B |
| NCT00672867 | PHASE3 | COMPLETED | A Pilot Study to Evaluate the Safety and Efficacy of Clevudine or Adefovir Patients With LC-B |
| NCT00000885 | PHASE2 | COMPLETED | Treatment Success and Failure in HIV-Infected Subjects Receiving Indinavir in Combination With Nucleoside Analogs: A Rollover Study for ACTG 320 |
| NCT00000912 | PHASE2 | COMPLETED | A Study on Amprenavir in Combination With Other Anti-HIV Drugs in HIV-Positive Patients |
| NCT00001087 | PHASE2 | COMPLETED | The Effectiveness of Nelfinavir and Efavirenz, Used Alone or Together, Combined With Other Anti-HIV Drugs in Patients Who Have Taken Anti-HIV Drugs |
| NCT00002184 | PHASE2 | COMPLETED | A Phase II, Stratified, Randomized, Double-Blind, Multi-Center Study of the Safety and Efficacy of Adefovir Dipivoxil (ADF) at Two Dose Levels in Triple Combination Therapies With Protease Inhibitors (PI) and Nucleoside Reverse Transcriptase Inhibitors (RTI) for the Treatment of HIV-Infected Patient |
| NCT00002219 | PHASE2 | UNKNOWN | Safety and Effectiveness of Adding Adefovir Dipivoxil and Nelfinavir to the Anti-HIV Therapy of HIV-Infected Children |
| NCT00002234 | PHASE2 | COMPLETED | Safety and Effectiveness of Giving an Anti-HIV Drug Combination of Adefovir Dipivoxil Plus Didanosine Plus Efavirenz Plus Lamivudine Once Daily to HIV-Infected Patients |
| NCT00002379 | PHASE2 | COMPLETED | The Safety and Effectiveness of Adefovir Dipivoxil Plus Indinavir Combined With Zidovudine or Lamivudine or Stavudine in HIV-Infected Patients Who Have Not Taken Anti-HIV Drugs |
| NCT00002419 | PHASE2 | COMPLETED | Safety and Effectiveness of Giving Adefovir Dipivoxil Plus Abacavir Plus Efavirenz Plus Amprenavir to HIV-Infected Patients Who Have Failed to Respond to Previous Protease Inhibitor Treatment |
| NCT00033163 | PHASE2 | COMPLETED | A Comparison of Adefovir and Tenofovir for the Treatment of Lamivudine-Resistant Hepatitis B Virus in People With HIV |
| NCT00051077 | PHASE2 | WITHDRAWN | Treatment of Hepatitis in Patients Who Are Triple-Infected With HIV, Hepatitis B Virus (HBV), and Hepatitis C Virus (HCV) |
| NCT00644761 | PHASE2 | COMPLETED | PK Study of Tacrolimus and Cyclosporine When Co-Administered With Adefovir Dipivoxil in Post-Liver Transplant Patients |
| NCT00645294 | PHASE1/PHASE2 | COMPLETED | Open Label Study of Pharmacokinetics and Safety of Dose of Adefovir Dipivoxil in Children and Adolescents With HBV |
| NCT00753467 | PHASE2 | UNKNOWN | A Phase II Study to Determine the Safety and Efficacy of Interferon-gamma in Patients With Chronic Hepatitis B |
| NCT01146808 | PHASE1/PHASE2 | COMPLETED | Adefovir Plus Vaccination in Transplant Patients Without Hepatitis B That Receive a Core Antibody Positive Liver |
| NCT02965859 | PHASE2 | UNKNOWN | The Safety and Dose-range Study of Metacavir Enteric-coated Capsules in Patients With Chronic Hepatitis B |
| NCT00000843 | PHASE1 | COMPLETED | The Safety and Effectiveness of Adefovir Dipivoxil in HIV-Infected Children |
| NCT00002128 | PHASE1 | COMPLETED | Phase I Study of the Safety, Tolerance, and Pharmacokinetics of 9-[2-(Bispivaloyloxymethyl)Phosphonylmethoxyethyl]Adenine (Bis-POM PMEA; Adefovir Dipivoxil) in HIV-Infected Patients |
| NCT00002206 | PHASE1 | COMPLETED | A Study of Adefovir Dipivoxil in HIV-Infected Patients Who Have Not Been Treated With Anti-HIV Drugs |
| NCT00002346 | PHASE1 | COMPLETED | The Safety and Effectiveness of Bis-POM PMEA in HIV-Infected Patients |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 2 clinical and 5 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).