File:Oseltamivir.svg · Wikimedia Commons · See Wikimedia Commons
oseltamivir
Sign in to saveAlso known as (−)-oseltamivir, (-)-oseltamivir, HSDB 7433, GS-4104, (3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid, LDD852, 1-cyclohexene-1-carboxylic acid, 4-(acetylamido)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R-(3alpha,4beta,5alpha))-, ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
Oseltamivir, sold under the brand name Tamiflu among others, is an antiviral medication used to treat and prevent influenza A and influenza B, viruses that cause the flu. Many medical organizations recommend it in people who have complications or are at high risk of complications within 48 hours of first symptoms of infection. They recommend it to prevent infection in those at high risk, but not the general population. The Centers for Disease Control and Prevention (CDC) recommends that clinicians use their discretion to treat those at lower risk who present within 48 hours of first symptoms o
Key facts
- Drug.image
- Oseltamivir.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Oseltamivir-based-on-dihydrogenphosphate-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Tamiflu, others
- Drug.MedlinePlus
- a699040
- Drug.DailyMedID
- Oseltamivir
- Drug.pregnancy_AU
- B1
- Drug.routes_of_administration
- By mouth
- Drug.class
- Neuraminidase inhibitor
- Drug.ATC_prefix
- J05
- Drug.ATC_suffix
- AH02
- Drug.legal_AU
- S4
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.bioavailability
- >80%
- Drug.protein_bound
- 42% (parent drug), 3% (active metabolite)
via Wikipedia infobox
Chemical data
- Formula
- C16H28N2O4
- Molecular weight
- 312.4 g/mol
- IUPAC name
- ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate
- SMILES
- CCC(CC)O[C@@H]1C=C(C[C@@H]([C@H]1NC(=O)C)N)C(=O)OCC
- InChIKey
- VSZGPKBBMSAYNT-RRFJBIMHSA-N
- XLogP
- 1.1
- Polar surface area
- 90.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
5,694 papers- Oseltamivir and acute hepatitis, reality association or coincidence?Antiviral therapy · 2021
- Oseltamivir.Journal of postgraduate medicine · 2009
- Does oseltamivir prevent hospitalisation in people with influenza?Drug and therapeutics bulletin · 2024
- Effectiveness of prolonged versus standard-course of oseltamivir in critically ill patients with severe influenza infection: A multicentre cohort study.Journal of medical virology · 2023
- Considerations when treating influenza infections with oseltamivir.Expert opinion on pharmacotherapy · 2024
via PubMed
Wikidata facts
- Mass
- 312.205
Show 7 more facts
- Commons category
- Oseltamivir
- chemical formula
- C₁₆H₂₈N₂O₄
- Commons gallery
- Oseltamivir
- canonical SMILES
- CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)OCC
- isomeric SMILES
- CCC(CC)O[C@@H]1C=C(C[C@@H]([C@H]1NC(=O)C)N)C(=O)OCC
- World Health Organisation international non-proprietary name
- oseltamivir
- defined daily dose
- 0.15
Sources (7)
via Wikidata · CC0
~20 min read
Article
21 sectionsContents
- Medical uses
- High-risk people
- Otherwise healthy people
- Prevention
- Side effects
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Resistance
- H1N1 flu or "swine flu"
- Seasonal flu
- H3N2
- Influenza B
- H5N1 avian influenza "bird flu"
- H7N9 avian influenza
- History
- Veterinary use
- Research
- References
- Further reading
- External links
Oseltamivir, sold under the brand name Tamiflu among others, is an antiviral medication used to treat and prevent influenza A and influenza B, viruses that cause the flu. Many medical organizations recommend it in people who have complications or are at high risk of complications within 48 hours of first symptoms of infection. They recommend it to prevent infection in those at high risk, but not the general population. The Centers for Disease Control and Prevention (CDC) recommends that clinicians use their discretion to treat those at lower risk who present within 48 hours of first symptoms of infection. It is taken by mouth, either as a pill or liquid.
Recommendations regarding oseltamivir are controversial as are criticisms of the recommendations. A 2014 Cochrane Review concluded that oseltamivir does not reduce hospitalizations, and that there is no evidence of reduction in complications of influenza. Two meta-analyses have concluded that benefits in those who are otherwise healthy do not outweigh its risks. They also found little evidence regarding whether treatment changes the risk of hospitalization or death in high risk populations. However, another meta-analysis found that oseltamivir was effective for prevention of influenza at the individual and household levels.