Oseltamivir
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Also known as GS 4104GS-4071 ETHYL ESTERGS-4104GS4104RO 640796RO-640796oseltamivircarboxylateoseltamivir carboxylateOsektanuvur carboxylateTamifluOseltamirvir-carboxylate[14C]OseltamivirOseltaminivOseltamivir phosphateÊOseltamivir phosphateÂOSELTAMIVIR PHOSPHATEOseltamivir
Summary
Oseltamivir (CHEMBL1229) is an approved small-molecule prodrug (ATC J05AH02); indicated across 11 conditions including viral infectious disease and autoimmune thrombocytopenic purpura.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J05AH02
- Indications: 11 conditions
- Clinical trials: 129
- Chemistry: 312.4 Da · C16H28N2O4
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1229 |
| Name | Oseltamivir |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 65028 |
| ChEBI | CHEBI:7798 |
| ATC | J05AH02 |
| Molecular formula | C16H28N2O4 |
| Molecular weight | 312.4 |
| InChIKey | VSZGPKBBMSAYNT-RRFJBIMHSA-N |
SMILES: CCC(CC)O[C@@H]1C=C(C[C@@H]([C@H]1NC(=O)C)N)C(=O)OCC
IUPAC name: ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate
ChEBI definition: A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.
Pharmacological roles (ChEBI): prodrug, EC 3.2.1.18 (exo-α-sialidase) inhibitor, antiviral drug.
Other ChEBI roles (chemical / environmental): environmental contaminant, xenobiotic.
Also known as: GS 4104, GS-4071 ETHYL ESTER, GS-4104, GS4104, Oseltamivir, RO 640796, RO-640796, oseltamivircarboxylate, oseltamivir, oseltamivir carboxylate, Oseltamivir carboxylate, Oseltamivir Carboxylate
Parent form; salt/anhydrous children: CHEMBL251990, CHEMBL1200340, CHEMBL3183419
Patent coverage: 6,577 distinct patent families (22,045 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: Neuraminidase, Neuraminidase, Neuraminidase, Neuraminidase, Sialidase.
Bioactivity
ChEMBL activities: 10 potent at pChembl ≥ 5 of 14 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P03474 | 8.96 | Ki | 1.1 | nM | CHEMBL_ACT_2079248 |
| P03469 | 8.86 | IC50 | 1.39 | nM | CHEMBL_ACT_15038922 |
| Q75VQ4 | 8.81 | IC50 | 1.55 | nM | CHEMBL_ACT_3539797 |
| P03469 | 8.59 | IC50 | 2.57 | nM | CHEMBL_ACT_15038929 |
| P03474 | 8.3 | IC50 | 5 | nM | CHEMBL_ACT_694726 |
| P03468 | 8.15 | IC50 | 7.09 | nM | CHEMBL_ACT_3539796 |
| P03468 | 7.3 | IC50 | 50 | nM | CHEMBL_ACT_19181727 |
| P03468 | 7.11 | IC50 | 77.6 | nM | CHEMBL_ACT_18322369 |
| P03468 | 5.58 | IC50 | 2600 | nM | CHEMBL_ACT_19181737 |
| P03468 | 5.39 | IC50 | 4071 | nM | CHEMBL_ACT_18686380 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
11 indications (0 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 | 3 | MONDO:0005108 | EFO:0000763 |
| autoimmune thrombocytopenic purpura | 3 | MONDO:0008558 | EFO:0007160 |
| influenza | 3 | MONDO:0005812 | EFO:0007328 |
| severe acute respiratory syndrome | 3 | MONDO:0005091 | MONDO:0100096 |
| pneumonia | 3 | MONDO:0005249 | EFO:0003106 |
| avian influenza | 2 | MONDO:0018695 | EFO:0005222 |
| thrombocytopenia | 2 | MONDO:0002049 | HP:0001873 |
| chronic kidney disease | 1 | MONDO:0005300 | EFO:0003884 |
| obesity disorder | 1 | MONDO:0011122 | EFO:0001073 |
2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 129.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 31 |
| PHASE4 | 30 |
| PHASE1 | 26 |
| PHASE2 | 24 |
| Not specified | 11 |
| PHASE1/PHASE2 | 4 |
| PHASE2/PHASE3 | 2 |
| EARLY_PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00304434 | PHASE4 | COMPLETED | Evaluation of Alternative Oseltamivir (Tamiflu) Dosing Strategies. |
| NCT00412555 | PHASE4 | COMPLETED | A Study of Tamiflu (Oseltamivir) for Seasonal Prophylaxis of Influenza in Children. |
| NCT00412737 | PHASE4 | COMPLETED | A Study of Oseltamivir (Tamiflu) for the Seasonal Prophylaxis of Influenza in Immunocompromised Participants |
| NCT00436124 | PHASE4 | TERMINATED | A Study of Tamiflu (Oseltamivir) Treatment in Laboratory-Confirmed Influenza. |
| NCT00593502 | PHASE4 | COMPLETED | Early Oseltamivir Treatment of Influenza in Children 1-3 Years of Age |
| NCT00935194 | PHASE4 | COMPLETED | Chinese Medicinal Herbs Treatment on Novel Influenza A (H1N1) : Multi-centre, Prospective, Randomized Controlled Study |
| NCT00936013 | PHASE4 | UNKNOWN | Chinese Medicinal Herbs Treatment on Novel Influenza A (H1N1)Pneumonia: Multi-centre, Prospective, Randomized Controlled Study |
| NCT00980109 | PHASE4 | COMPLETED | Long Term Influenza Prophylaxis With Inhaled Zanamivir or Oral Oseltamivir |
| NCT01032837 | PHASE4 | TERMINATED | A Study of Tamiflu (Oseltamivir) for Treatment of Influenza With a Focus on (H1N1) 2009 Flu Strain |
| NCT01052961 | PHASE4 | COMPLETED | A Study on Higher-dose Oseltamivir Treatment’s Impact on Viral Clearance and Clinical Recovery in Adults Hospitalized With Influenza |
| NCT01053377 | PHASE4 | UNKNOWN | A Randomised Controlled Trial on the Effect of Post-exposure Oseltamivir Prophylaxis on Influenza Transmission in Nursing Homes |
| NCT01130636 | PHASE4 | COMPLETED | Observational Study on the Pharmacokinetics of Oseltamivir in the Treatment of Influenza During Lactation |
| NCT01248715 | PHASE4 | COMPLETED | Rapid Empiric Treatment With Oseltamivir Study (RETOS) |
| NCT01249833 | PHASE4 | COMPLETED | Effect of Oseltamivir on Cognitive Function in Subjects With Influenza |
| NCT01443806 | PHASE4 | COMPLETED | Characterisation of the Human Carboxylesterase 1 (CES1) Mutations in Thailand |
| NCT01456234 | PHASE4 | TERMINATED | Time to Oseltamivir Access When Prescribed by Pharmacists Versus Physicians (ACCESS) |
| NCT01690637 | PHASE4 | TERMINATED | Panama and El Salvador Children’s Oseltamivir Study |
| NCT01804946 | PHASE4 | COMPLETED | Clinical Trial of Clinical Efficiency and Safety of Ergoferon in Treatment of Influenza |
| NCT01850446 | PHASE4 | COMPLETED | Comparative Clinical Trial of Efficacy and Safety of Ergoferon Versus Oseltamivir in Treatment of Influenza |
| NCT02232945 | PHASE4 | UNKNOWN | Banlangen Granules Anti-seasonal Influenza Study |
| NCT02282384 | PHASE4 | WITHDRAWN | An RCT of Oseltamivir in Outpatients With CPD: A Pilot Study. |
| NCT02561169 | PHASE4 | TERMINATED | A Trial of Oseltamivir in High-Risk Patients Presenting to the Emergency Department With Influenza |
| NCT02609399 | PHASE4 | COMPLETED | ED Influenza Therapeutic Pilot Study: Oseltamivir vs. Peramivir |
| NCT02780622 | PHASE4 | COMPLETED | A Pharmacokinetics, Pharmacodynamics and Safety Study of Warfarin in Combination With Tamiflu (Oseltamivir) |
| NCT03754686 | PHASE4 | UNKNOWN | Oseltamivir Versus Paracetamol for Influenza-like Illness During the Influenza Season |
| NCT04183725 | PHASE4 | UNKNOWN | Clinical Study of Reduning Injection for the Treatment of Influenza in Children |
| NCT04255017 | PHASE4 | UNKNOWN | A Prospective/Retrospective,Randomized Controlled Clinical Study of Antiviral Therapy in the 2019-nCoV Pneumonia |
| NCT04536415 | PHASE4 | COMPLETED | Bioequivalence Study of Oseltamivir Phosphate and TAMIFLU Under Fed Condition in Healthy Volunteers |
| NCT04684498 | PHASE4 | UNKNOWN | Open-label Study of Neuraminidase Inhibitor Treatment in STEMI Patients |
| NCT05012189 | PHASE4 | UNKNOWN | Baloxavir Versus Oseltamivir for Nursing Home Influenza Outbreaks |
| NCT02735707 | PHASE3 | RECRUITING | Randomized, Embedded, Multifactorial Adaptive Platform Trial for Community- Acquired Pneumonia |
| NCT04381936 | PHASE3 | RECRUITING | Randomised Evaluation of COVID-19 Therapy |
| NCT07113392 | PHASE3 | NOT_YET_RECRUITING | A Study to Evaluate the Safety, Efficacy and Pharmacokinetics of Suraxavir Marboxil for Suspension |
| NCT07229807 | PHASE3 | ACTIVE_NOT_RECRUITING | Efficacy and Safety of ZSP1273 in Children 2-11 Years Old With Influenza A |
| NCT07236814 | PHASE3 | RECRUITING | Suraxavir Marboxil And Oseltamivir for Influenza Prophylaxis Under a Hospital-based Setting |
| NCT07357051 | PHASE3 | RECRUITING | Phase III Clinical Study Evaluating the Safety, Pharmacokinetics, and Efficacy of JKN2301 Dry Suspension in Pediatric Patients Aged 2 to Under 12 Years With Influenza |
| NCT07496736 | PHASE3 | ACTIVE_NOT_RECRUITING | Post-exposure Influenza Prophylaxis in a Hospital Setting |
| NCT00545532 | PHASE3 | COMPLETED | A Study of Oseltamivir (Tamiflu) for Treatment of Influenza in Immunocompromised Participants. |
| NCT00707941 | PHASE3 | COMPLETED | Oseltamivir Randomised Controlled Efficacy Trial |
| NCT00799760 | PHASE3 | TERMINATED | Evaluation of Efficacity and Safety of Oseltamivir and Zanamivir |
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 11 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).