Oseltamivir

Oseltamivir

Clinical data
Pronunciation	/ɒsəlˈtæmᵻvɪər/
Trade names	Tamiflu
AHFS/Drugs.com	Monograph
MedlinePlus	a699040
License data	US DailyMed: 48517
Pregnancy category	AU: B1 US: C (Risk not ruled out)
Routes of administration	By mouth (hard capsules)
ATC code	J05AH02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: Prescription only
Pharmacokinetic data
Bioavailability	>80%
Protein binding	42% (parent drug), 3% (active metabolite)
Metabolism	Hepatic, to oseltamivir carboxylate
Biological half-life	1-3 hours, 6-10 hours (active metabolite)
Excretion	Urine (>90% as oseltamivir carboxylate), faeces
Identifiers
IUPAC name ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)-cyclohex-1-ene-1-carboxylate
CAS Number	204255-11-8 N
PubChem (CID)	65028
DrugBank	DB00198 Y
ChemSpider	58540 Y
UNII	20O93L6F9H Y
KEGG	D08306 Y
ChEBI	CHEBI:7798 Y
ChEMBL	CHEMBL1229 Y
ECHA InfoCard	100.169.154
Chemical and physical data
Formula	C16H28N2O4
Molar mass	312.4 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(OCC)/C1=C/[C@@H](OC(CC)CC)[C@H](NC(=O)C)[C@@H](N)C1
InChI InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1 Y Key:VSZGPKBBMSAYNT-RRFJBIMHSA-N Y
NY (what is this?)

Oseltamivir, sold under the brand name Tamiflu, is an antiviral medication used to treat and prevent influenza A and influenza B (flu). Many medical organizations recommend its use in people who have complications or are at high risk of complications within 48 hours of first symptoms of infection. They recommend its use to prevent infection in those at high-risk but not the general population. The 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 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.

Common side effects include vomiting, diarrhea, headache, and trouble sleeping. Other side effects may include psychiatric symptoms and seizures. Oseltamivir has been taken by a small number of pregnant women without signs of problems. In the United States use is recommended if influenza occurs during pregnancy. Dose adjustment may be needed in those with kidney problems.

Oseltamivir was approved for medical use in the United States in 1999. It was the first neuraminidase inhibitor available by mouth. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. A generic version was approved in the United States in 2016. The wholesale cost in the developing world in 2014 was about US$4.27 per day. In the United States a course of treatment cost US$138.70 as of December 2016.