Darunavir
drugOn this page
Also known as (-)-darunavirDarunavir component of prezcobixDarunavir component of symtuzaDarunavir krkaDarunavir krka d.d.PrezistaTMC 114TMC-114TMC-41629TMC114UIC-94017UIC-940TSID50113275SID144206187Darunavir Ethanolate (Prezista)
Summary
Darunavir (CHEMBL1323) is an approved small-molecule HIV protease inhibitor (ATC J05AE10); indicated across 10 conditions including hiv infectious disease and viral infectious disease.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J05AE10
- Indications: 10 conditions
- Clinical trials: 125
- Chemistry: 547.7 Da · C27H37N3O7S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1323 |
| Name | Darunavir |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 213039 |
| ChEBI | CHEBI:367163 |
| ATC | J05AE10 |
| Molecular formula | C27H37N3O7S |
| Molecular weight | 547.7 |
| InChIKey | CJBJHOAVZSMMDJ-HEXNFIEUSA-N |
SMILES: CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CO[C@@H]3[C@H]2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)N
IUPAC name: [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
ChEBI definition: An N,N-disubstituted benzenesulfonamide bearing an unsubstituted amino group at the 4-position, used for the treatment of HIV infection. A second-generation HIV protease inhibitor, darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including those from treatment-experienced patients with multiple resistance mutations to other protease inhibitors.
Pharmacological roles (ChEBI): HIV protease inhibitor, antiviral drug.
Also known as: (-)-darunavir, Darunavir, Darunavir component of prezcobix, Darunavir component of symtuza, Darunavir krka, Darunavir krka d.d., Prezista, TMC 114, TMC-114, TMC-41629, TMC114, UIC-94017
Parent form; salt/anhydrous children: CHEMBL1201127
Patent coverage: 4,183 distinct patent families (15,382 SureChEMBL compound mentions), from 1 matched compound structure(s). 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: 5 (assay-derived). Sample: A-type voltage-gated potassium channel KCND3, Sodium channel protein type 5 subunit alpha, Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK), Voltage-gated inwardly rectifying potassium channel KCNH2, ATP-dependent translocase ABCB1.
Bioactivity
ChEMBL activities: 1 potent at pChembl ≥ 5 of 10 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| ABCB1 | 5.18 | IC50 | 6600 | nM | CHEMBL_ACT_19257519 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
10 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 |
|---|---|---|---|
| HIV infectious disease | 4 | MONDO:0005109 | EFO:0000764 |
| viral infectious disease | 4 | MONDO:0005108 | EFO:0000763 |
| AIDS | 3 | MONDO:0012268 | EFO:0000765 |
| pneumocystosis | 3 | MONDO:0019121 | EFO:0007448 |
| severe acute respiratory syndrome | 3 | MONDO:0005091 | MONDO:0100096 |
| hepatitis C virus infection | 1 | MONDO:0005231 | EFO:0003047 |
| amyotrophic lateral sclerosis | 1 | MONDO:0004976 | MONDO:0004976 |
3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 125.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE1 | 37 |
| PHASE4 | 27 |
| PHASE3 | 25 |
| PHASE2 | 18 |
| Not specified | 14 |
| PHASE1/PHASE2 | 3 |
| PHASE2/PHASE3 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT06787976 | PHASE4 | NOT_YET_RECRUITING | Effect of Dolutegravir Compared With Darunavir/Cobicistat on the Severity of Neuropsychiatric Effects al 12 Weeks in Antirretroviral Treatment-Naive Adults. |
| NCT00531557 | PHASE4 | COMPLETED | Double Protease Inhibitor to Darunavir Switch Study |
| NCT00543101 | PHASE4 | COMPLETED | Efficacy Study of Substitution of Darunavir/Ritonavir (DRV/r) for Dual-boosted Protease Inhibitors |
| NCT00630734 | PHASE4 | COMPLETED | Genetic Predictors of Variability in the Drug-drug Interaction Between Darunavir/Ritonavir and Pravastatin |
| NCT00677300 | PHASE4 | COMPLETED | Raltegravir And Darunavir Antiretroviral in Antiretroviral Naive Patients |
| NCT00757783 | PHASE4 | COMPLETED | Changes in Triglyceride and Other Lipids (Levels of Fats Found in Blood) When Taking Darunavir Compared to Atazanavir in HIV-infected Patients That Have Never Received Treatment |
| NCT00765154 | PHASE4 | TERMINATED | NNRTI/PI Toxicity Switch to Darunavir Study |
| NCT00855413 | PHASE4 | TERMINATED | HIV Viremia and Persistence in Acutely HIV-Infected Patients Treated With Darunavir/Ritonavir and Etravirine |
| NCT00994344 | PHASE4 | COMPLETED | Clinical Study to Evaluate the Efficacy and Safety of Lopinavir/Ritonavir Monotherapy Versus Darunavir/Ritonavir Monotherapies as Simplification Switching Strategies of PI/NNRTI-Triple Therapy Based-Regimens |
| NCT01013987 | PHASE4 | UNKNOWN | Maraviroc (Celsentri) With Raltegravir and Darunavir/Ritonavir for the Treatment of Triple Class Failure in Adult HIV-1 Infected Patients |
| NCT01118871 | PHASE4 | TERMINATED | The First Failure Study |
| NCT01274780 | PHASE4 | COMPLETED | Metabolic Effects of Atazanavir/Ritonavir Versus Darunavir/Ritonavir in Combination With Tenofovir/Emtricitabine in naïve HIV-1 Infected Patients |
| NCT01422369 | PHASE4 | COMPLETED | Drug-Drug Interaction of Darunavir/Ritonavir on Pitavastatin |
| NCT01641367 | PHASE4 | COMPLETED | A5288/MULTI-OCTAVE: Management Using Latest Technologies to Optimize Combination Therapy After Viral Failure |
| NCT01702090 | PHASE4 | COMPLETED | Early Access to Low-dose Ritonavir (TMC114/r) and Other Antiretrovirals (ARVs) for Treatment-naive or Early Treatment Experienced in HIV-1 Patients |
| NCT01810887 | PHASE4 | COMPLETED | A Phase 4 Study to Evaluate Pharmacokinetics and Safety of Darunavir Along With Ritonavir in Healthy Male Japanese Participants |
| NCT01928407 | PHASE4 | COMPLETED | Evaluation of the Efficacy and Safety Between Two Antiretroviral Regimens, in HIV-1-infected Treatment-naïve Subjects With Low CD4 Counts |
| NCT02159599 | PHASE4 | COMPLETED | Study to Evaluate Darunavir/Ritonavir + Lamivudine Versus Continuing With Darunavir/Ritonavir + Tenofovir/Emtricitabine or Abacavir/Lamivudine in HIV Infected Subject |
| NCT02404233 | PHASE4 | UNKNOWN | Open Label, Pilot Study of Darunavir Boosted by Cobicistat in Combination With Rilpivirine to Treat HIV+ Naïve Subjects |
| NCT02470650 | PHASE4 | WITHDRAWN | Cost-effectiveness of Different Antiretroviral Treatment in Patients HIV Naive |
| NCT02503462 | PHASE4 | TERMINATED | Effect of Cobicistat Versus Ritonavir Boosting on the Brain Permeation of Darunavir in HIV-infected Individuals |
| NCT02770508 | PHASE4 | COMPLETED | Darunavir/Ritonavir + Lamivudine Versus Darunavir/Ritonavir +Emtricitabine/Tenofovir in Naïve HIV-1 Infected Subjects |
| NCT03017872 | PHASE4 | UNKNOWN | Dolutegravir and Darunavir Evaluation in Adults Failing Therapy |
| NCT03101644 | PHASE4 | COMPLETED | Optimization of Darunavir Therapy and Dosage Recommendations |
| NCT03123848 | PHASE4 | COMPLETED | A Study to Evaluate the Pharmacokinetics (PK) of Darunavir (DRV) and Cobicistat (COBI) After a Single Oral Administration of Darunavir/Cobicistat Fixed-Dose Combination in Healthy Japanese Adult Participants |
| NCT04183738 | PHASE4 | WITHDRAWN | Inflammation and Co-Infections in D²EFT |
| NCT04388904 | PHASE4 | COMPLETED | Rapid Reinitiation of a Single Tablet Antiretroviral Therapy Using Symtuza® in HIV-1 Infected Treatment-Experienced Patients Off Therapy. (ReSTART) |
| NCT06747507 | PHASE3 | RECRUITING | Ndovu RCT: Investing the Optimal Management of Dolutegravir Resistance |
| NCT00110877 | PHASE3 | COMPLETED | TMC114-C214: Trial of TMC114 Administered With Low Dose Ritonavir (RTV) in HIV-1 Infected Treatment Experienced Patients |
| NCT00115050 | PHASE3 | COMPLETED | TMC114-C209: A Study of Safety of TMC114 With Low Dose Ritonavir (RTV) and Other Antiretrovirals in Experienced HIV-1 Infected Patients With Limited or no Treatment Options |
| NCT00258557 | PHASE3 | COMPLETED | TMC114-C211: Trial of an Investigational Protease Inhibitor TMC114 With Ritonavir (TMC114/r) in HIV-1 Infected Patients Who Have Never Been Treated With Antiretroviral Medications. |
| NCT00381303 | PHASE3 | COMPLETED | GRACE: A Study to Compare the Effectiveness, Safety and Tolerability of PREZISTA (Darunavir)/Ritonavir by Gender and Race When Administered With Other Antiretroviral Medications in Human Immunodeficiency Virus (HIV) Positive Women and Men. |
| NCT00421551 | PHASE3 | COMPLETED | Study Comparing Efficacy and Safety of Darunavir Boosted With Ritonavir to HART With 2 NRTI and Darunavir Boosted With Ritonavir in HIV-1 Infected Patients ANRS136 |
| NCT00517192 | PHASE3 | TERMINATED | Comparison of TPV/r to DRV/r in Triple Class Experienced Patient With Resistance to > 1 PI |
| NCT00524368 | PHASE3 | COMPLETED | A Study to Compare Effectiveness and Safety of Darunavir/Ritonavir (DRV/Rtv) 800mg/100mg Once Daily Versus DRV/Rtv 600mg/100mg Twice Daily in Early Treatment-Experienced HIV-1 Infected Patients (ODIN) |
| NCT00537394 | PHASE3 | COMPLETED | Optimizing Treatment for Treatment-Experienced, HIV-Infected People |
| NCT00811954 | PHASE3 | COMPLETED | Comparative Study of Three NNRTI-Sparing HAART Regimens |
| NCT00849160 | PHASE3 | COMPLETED | Study of Protease Inhibitor Regimen Switch in HIV-1 Infected Patients With Undetectable Viral Load to Prove the Non-inferiority of Once Daily Dose Regimen Versus the Current Twice Daily Regimen to Maintain the Viral Load Under the Limit of Detection. |
| NCT00855335 | PHASE3 | COMPLETED | A Single-arm, Open-label, Study to Assess the Pharmacokinetics of Darunavir and Ritonavir, Darunavir and Cobicistat, Etravirine, and Rilpivirine in HIV-1 Infected Pregnant Women |
| NCT01066962 | PHASE3 | COMPLETED | Study of Darunavir/r + Tenofovir/Emtricitabine vs. Darunavir/r + Raltegravir in HIV-infected Antiretroviral naïve Subjects |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 2 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).