Tenofovir Disoproxil
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Also known as (r)-bis(poc)pmpaBis-poc-pmpaGS-4331VireadTENOFOVIR DISOPROXIL FUMARATETENOFOVIR-DISOPROXIL
Summary
Tenofovir Disoproxil (CHEMBL1538) is an approved small-molecule prodrug (ATC J05AF07); indicated across 9 conditions including viral infectious disease and hiv infectious disease.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J05AF07
- Indications: 9 conditions
- Clinical trials: 189
- Chemistry: 519.4 Da · C19H30N5O10P
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1538 |
| Name | Tenofovir Disoproxil |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 5481350 |
| ChEBI | CHEBI:63717 |
| ATC | J05AF07 |
| Molecular formula | C19H30N5O10P |
| Molecular weight | 519.4 |
| InChIKey | JFVZFKDSXNQEJW-CQSZACIVSA-N |
SMILES: C[C@H](CN1C=NC2=C(N=CN=C21)N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C
IUPAC name: [[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate
ChEBI definition: An organic phosphonate that is the disoproxil ester of tenofovir. A prodrug for tenofovir, an HIV-1 reverse transcriptase inhibitor, tenofovir disoproxil is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.
Pharmacological roles (ChEBI): prodrug, HIV-1 reverse transcriptase inhibitor, antiviral drug.
Also known as: (r)-bis(poc)pmpa, Bis-poc-pmpa, GS-4331, Tenofovir disoproxil, Viread, TENOFOVIR DISOPROXIL, TENOFOVIR DISOPROXIL FUMARATE, Tenofovir Disoproxil Fumarate, TENOFOVIR-DISOPROXIL
Parent form; salt/anhydrous children: CHEMBL1486, CHEMBL3185360, CHEMBL4594453, CHEMBL6068332, CHEMBL6068341
Patent coverage: 2,410 distinct patent families (7,909 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 7,850 (99%) 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: 2 (assay-derived). Sample: Gag-Pol polyprotein, Prolyl endopeptidase FAP.
Bioactivity
ChEMBL activities: 5 potent at pChembl ≥ 5 of 5 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| FAP | 6.05 | Ki | 890 | nM | CHEMBL_ACT_29108084 |
| P04585 | 5.99 | IC50 | 1036 | nM | CHEMBL_ACT_26686565 |
| FAP | 5.75 | IC50 | 1800 | nM | CHEMBL_ACT_29108097 |
| P04585 | 5.27 | IC50 | 5390 | nM | CHEMBL_ACT_26686553 |
| P04585 | 5.19 | IC50 | 6515 | nM | CHEMBL_ACT_26686550 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
9 indications (1 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 |
|---|---|---|---|
| viral infectious disease | 4 | MONDO:0005108 | EFO:0000763 |
| HIV infectious disease | 3 | MONDO:0005109 | EFO:0000764 |
| severe acute respiratory syndrome | 3 | MONDO:0005091 | MONDO:0100096 |
| hepatitis B virus infection | 2 | MONDO:0005344 | EFO:0004197 |
| chronic hepatitis C virus infection | 2 | MONDO:0005354 | EFO:0004220 |
| hepatitis D virus infection | 2 | MONDO:0005789 | EFO:0007304 |
| chronic hepatitis B virus infection | 2 | MONDO:0005366 | EFO:0004239 |
| primary biliary cholangitis | 2 | MONDO:0005388 | EFO:1001486 |
| hepatitis | 1 | MONDO:0002251 | HP:0012115 |
Clinical trials
Total trials: 189.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 47 |
| PHASE4 | 44 |
| PHASE2 | 37 |
| PHASE3 | 29 |
| PHASE1 | 22 |
| PHASE1/PHASE2 | 5 |
| PHASE2/PHASE3 | 3 |
| EARLY_PHASE1 | 2 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT04032860 | PHASE4 | ACTIVE_NOT_RECRUITING | RCT of Different Effects of Nucleot(s)Ide Analogues on the Prognosis of HBV-HCC Patients After Curative Resection |
| NCT00055120 | PHASE4 | COMPLETED | When to Start Anti-HIV Drugs in Patients With Opportunistic Infections |
| NCT00084136 | PHASE4 | COMPLETED | Prospective Evaluation of Anti-retroviral Combinations for Treatment Naive, HIV Infected Persons in Resource-limited Settings |
| NCT00324688 | PHASE4 | COMPLETED | Safety Study of Once a Day ART and Opiate Substitute. |
| NCT00442962 | PHASE4 | COMPLETED | HIV Treatment Reinitiation in Women Who Received Anti-HIV Drugs to Prevent Mother-to-Child Transmission of HIV |
| NCT00647244 | PHASE4 | COMPLETED | Efficacy and Safety of Switching From Retrovir to Tenofovir or Abacavir in HIV-infected Patients |
| NCT00648817 | PHASE4 | COMPLETED | Metabolic Impact Assessment of Tenofovir Disoproxil Fumarate on Non-HIV-1 Infected Healthy Adult Male Volunteers |
| NCT00736190 | PHASE4 | COMPLETED | A Study to Evaluate Tenofovir Disoproxil Fumarate (DF) in Asian-American Adults With Chronic Hepatitis B Infection |
| NCT00998582 | PHASE4 | TERMINATED | Artery Elasticity After Switch From Epzicom to Truvada |
| NCT01234116 | PHASE4 | COMPLETED | Post-Exposure Prophylaxis in Health Care Workers |
| NCT01285050 | PHASE4 | COMPLETED | Interferon Alfa Sensitivity in HIV/HCV Persons Before and After HIV Meds |
| NCT01379508 | PHASE4 | COMPLETED | Telbivudine or Tenofovir Treatment in HBeAg-negative Chronic Hepatitis B Patients Based on the Roadmap Concept |
| NCT01458977 | PHASE4 | COMPLETED | Trial To Assess The Lipid-Lowering Effect Of Adding Tenofovir/Emtricitabine Co-Formulation Vs Placebo To Hiv-1-Infected Subjects With Dyslipidemia And Sustained Viral Load Suppression Under Monotherapy With Ritonavir-Boosted Protease Inhibitors |
| NCT01491295 | PHASE4 | UNKNOWN | Switch to Tenofovir Versus Continue Lamivudine/Adefovir Treatment in Lamivudine-resistance Chronic Hepatitis B Patients |
| NCT01641367 | PHASE4 | COMPLETED | A5288/MULTI-OCTAVE: Management Using Latest Technologies to Optimize Combination Therapy After Viral Failure |
| NCT01777997 | PHASE4 | COMPLETED | FTC/RPV/TDF on T-Cell Activation, CD4+ T-Cell Count, Inflammatory Biomarkers and Viral Reservoir |
| NCT02195518 | PHASE4 | COMPLETED | Tenofovir Disoproxil Fumarate (TDF) 300mg 3 Years RD Therapy Chinese Chronic Hepatitis B (CHN) CHB Multiple Nucleos(t)Ide Analogues (NAs) Failure Points Pts PH4 PMS Study |
| NCT02198443 | PHASE4 | COMPLETED | Comparison of Two Combinations in Antiretroviral Post-Exposure Prophylaxis for HIV-1: Tenofovir/Emtricitabine (Truvada ®) + Lopinavir/Ritonavir (Kaletra ®) vs Tenofovir/Emtricitabine/Cobicistat/Elvitegravir (Stribild ®). Prospective, Randomized, Open. |
| NCT02206555 | PHASE4 | COMPLETED | PrEP Demonstration Project (PRELUDE Study) |
| NCT02224456 | PHASE4 | COMPLETED | Efficacy and Safety Study of Tenofovir Disoproxil Fumarate (TDF) in Chinese Chronic Hepatitis B (CHB) Subjects With Advanced Fibrosis & Compensated Cirrhosis |
| NCT02308319 | PHASE4 | UNKNOWN | Prompt Or Watchful Monitoring for Hepatitis B Virus Related Hepatocellular Carcinoma Without Elevated viRal Load |
| NCT02322099 | PHASE4 | TERMINATED | Alendronate for Prevention of AntiRetroviral Therapy-associated Bone Loss |
| NCT02447016 | PHASE4 | TERMINATED | Decrease of Neuropsychiatric Side Effects After Switching From Atripla to Eviplera |
| NCT02463019 | PHASE4 | UNKNOWN | Roll-over After 3-year Trial for Tenofovir in Mild Chronic Hepatitis B |
| NCT02530060 | PHASE4 | COMPLETED | A Study to Evaluate the Pharmacokinetics of Rilpivirine/Tenofovir/Emtricitabine After a Single-Oral Administration in Healthy Japanese Adult Male Participants |
| NCT02560649 | PHASE4 | UNKNOWN | An Exploratory Study of RGT Strategy on Optimal NUC-experienced Patients |
| NCT02774837 | PHASE4 | UNKNOWN | Tenofovir Versus Tenofovir + Telbivudine for Chronic Hepatitis B |
| NCT02935075 | PHASE4 | COMPLETED | Optimization of Antiretroviral Therapy |
| NCT02937779 | PHASE4 | UNKNOWN | Tenofovir As Prevention Of Hepatitis b Mother-to-child Transmission |
| NCT03058835 | PHASE4 | UNKNOWN | IN-US-276-1340: Pre-Exposure Prophylaxis to Prevent HIV Acquisition in US Women: A Demonstration Project |
| NCT03241641 | PHASE4 | COMPLETED | Switching From TDF to TAF vs. Maintaining TDF in Chronic Hepatitis B With Resistance to Adefovir or Entecavir. |
| NCT03258710 | PHASE4 | COMPLETED | A Study of Switching From Entecavir to Tenofovir Disoproxil Fumarate in Subjects With Chronic Hepatitis B |
| NCT03357822 | PHASE4 | UNKNOWN | A Real-World Study of Pegylated Interferon In Nucleoside-treated Patients With Chronic Hepatitis B |
| NCT03468907 | PHASE4 | COMPLETED | The Safety of Anti-viral Therapy in Preventing HBV MTCT in Pregnant Women After Discontinuation |
| NCT03485534 | PHASE4 | COMPLETED | Evaluate the Efficacy and Safety to Tenofovir Disoproxil in Chronic Hepatitis B Patients |
| NCT03567382 | PHASE4 | COMPLETED | Arresting Vertical Transmission of Hepatitis B Virus |
| NCT04298697 | PHASE4 | COMPLETED | Biomarkers for Event-driven PrEP Adherence |
| NCT04640129 | PHASE4 | UNKNOWN | HBsAg Seroclearance in Adults With HBV Related Liver Fibrosis After Receiving Combined Therapy of Peg-IFN and Tenofovir. |
| NCT04671563 | PHASE4 | COMPLETED | Pharmacokinetics of Two Formulation of Tenofovir Disoproxil Fumarate |
| NCT05282407 | PHASE4 | COMPLETED | A phase4 Clinical Study to Evaluate the Safety and Efficacy of Switching to Tenofovir Disoproxil From Tenofovir Disoproxil Fumarate in Patients With Chronic Hepatitis B |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No PharmGKB pharmacogenomic data curated for this drug.
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).