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Identification
- Summary
Oseltamivir is a neuraminidase inhibitor used in the prophylaxis and treatment of influenza.
- Brand Names
- Ebilfumin, Tamiflu
- Generic Name
- Oseltamivir
- DrugBank Accession Number
- DB00198
- Background
Oseltamivir (marketed as the product TamifluⓇ), is an antiviral neuraminidase inhibitor used for the treatment and prophylaxis of infection with influenza viruses A (including pandemic H1N1) and B. Oseltamivir exerts its antiviral activity by inhibiting the activity of the viral neuraminidase enzyme found on the surface of the virus, which prevents budding from the host cell, viral replication, and infectivity.
The clinical benefit of use of oseltamivir is greatest when administered within 48 hours of the onset of influenza symptoms since effectiveness decreases significantly after that point in time; there is generally no benefit in use beyond 48 hours for healthy, low-risk individuals as influenza is a self-limiting illness.10,19,11 However, antiviral treatment might be beneficial when initiated after 48 hours for patients with severe, complicated or progressive illness or for hospitalized patients.12 According to the CDC, data from clinical trials and observational studies have demonstrated that early antiviral treatment can shorten the duration of fever and illness symptoms, and may reduce the risk of some complications (including pneumonia and respiratory failure). They recommend the use of oseltamivir in people with a higher risk of developing complications including children younger than 2 years, people over 65 years, people with some chronic conditions or immunosuppression, pregnant women, residents of long term care facilities, and indigenous communities for example.18
The benefits of oseltamivir use are controversial; a 2014 Cochrane Review of the evidence found that oseltamivir treatment had limited benefit. The authors concluded that oseltamivir use in healthy adults had small, non-specific effects on symptoms (where the time to first alleviation of symptoms was only reduced from 7 to 6.3 days), it had no effect on hospitalizations, and that there was no evidence for any reductions in complications of influenza such as pneumonia.7,8,9 Due to the risk of adverse effects such as nausea, vomiting, psychiatric effects and renal adverse events in adults and vomiting in children, the harms are generally considered to outweigh the small clinical benefit of use of oseltamivir.
Notably, in 2017, the World Health Organization downgraded oseltamivir from its essential medicines list from a "core" drug to a "complementary" drug, due to limited cost-effectiveness.6 Yearly vaccination with the influenza vaccine is still considered the best preventative measure.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Oseltamivir (DB00198)
- Weight
- Average: 312.4045
Monoisotopic: 312.204907394 - Chemical Formula
- C16H28N2O4
- Synonyms
- (−)-oseltamivir
- 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-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
- Oséltamivir
- Oseltamivirum
- External IDs
- GS 4104
- GS-4071 ETHYL ESTER
- GS-4104
- GS4104
- HSDB 7433
- RO-64-0796
- RO-640796
- RO64-0796
Pharmacology
- Indication
According to FDA prescribing information, oseltamivir is indicated for the treatment of acute, uncomplicated illness due to influenza A and B infection in patients 2 weeks of age and older who have been symptomatic for no more than 48 hours 20. In particular, this agent is indicated in adults and children including full-term neonates who present with symptoms typical of influenza when influenza virus is circulating in the community. Efficacy has been demonstrated when treatment is initiated within two days of the first onset of symptoms.21
Oseltamivir is also indicated for the prophylaxis of influenza in patients one year and older 20. Specifically, post-exposure prevention in individuals one year of age or older following contact with a clinically diagnosed influenza case when influenza virus is circulating in the community qualifies for such prophylactic therapy. Oseltamivir would only be indicated for post-exposure prevention of influenza in infants less than 1 year of age during a pandemic influenza outbreak. 21
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Flu caused by influenza •••••••••••• •••••• •••••• •••••••• •••••••••• •••••••• ••••••••••• ••••••• Prophylaxis of Flu caused by influenza •••••••••••• •••••• •••••••• •••••••••• •••••••• •••••••••••• ••••• ••••••• Prophylaxis of Flu caused by influenza •••••••••••• •••••• ••••••••• •••••• ••••••• Treatment of Flu caused by influenza •••••••••••• •••••• ••••••••• •••••• ••••••• Prophylaxis of Flu caused by influenza •••••••••••• •••••• ••••••••• •••••• •••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
There have been postmarketing reports of delirium and abnormal behavior leading to injury, and in some cases resulting in fatal outcomes, in patients with influenza who were receiving oseltamivir. Because these events were reported voluntarily during clinical practice, estimates of frequency cannot be made but they appear to be uncommon based on oseltamivir. These events were reported primarily among pediatric patients and often had an abrupt onset and rapid resolution. The contribution of oseltamivir to these events has not been established. Influenza can be associated with a variety of neurologic and behavioral symptoms that can include events such as hallucinations, delirium, and abnormal behavior, in some cases resulting in fatal outcomes. These events may occur in the setting of encephalitis or encephalopathy but can occur without obvious severe disease.21,13,14
- Mechanism of action
Oseltamivir phosphate is a pro-drug of the active metabolite (oseltamivir carboxylate) which is a potent and selective inhibitor of influenza virus neuraminidase enzymes, which are glycoproteins found on the virion surface. Viral neuraminidase enzyme activity is important for viral entry into uninfected cells, for the release of recently formed virus particles from infected cells, and for the further spread of the infectious virus in the body.21,15,22 Oseltamivir activity reduces viral shedding and infectivity.
Oseltamivir is effective agaisnt viral neuraminidases of influenza A (including pandemic H1N1) and influenza B.21,15,22
Target Actions Organism ANeuraminidase inhibitorInfluenza A virus (strain A/Chile/1/1983 H1N1) USialidase-1 inhibitorHumans USialidase-2 inhibitorHumans - Absorption
Oseltamivir is readily absorbed from the gastrointestinal tract after oral administration of oseltamivir phosphate and is extensively converted by predominantly hepatic esterases to the active metabolite oseltamivir carboxylate. At least 75 % of an oral dose reaches the systemic circulation as the active metabolite. Exposure to the pro-drug is less than 5 % relative to the active metabolite. Plasma concentrations of both pro-drug and active metabolite are proportional to dose and are unaffected by co-administration with food.20,21,15,22 Pharmacokinetic parameters following twice daily dosing of oseltamivir 75mg capsules are as follows: Cmax of oseltamivir and oseltamivir carboxylate were found to be 65ng/mL and 348ng/mL, respectively, while AUC (0-12h) of oseltamivir and oseltamivir carboxylate were found to be 112ng·h/mL and 2719ng·h/mL, respectively.21
- Volume of distribution
The mean volume of distribution at steady state of the oseltamivir carboxylate ranges approximately between 23 and 26 liters in humans, a volume that is roughly equivalent to extracellular body fluid. Since neuraminidase activity is extracellular, oseltamivir carboxylate distributes to all sites of influenza virus spread.20,21,15,22
- Protein binding
The binding of the active oseltamivir carboxylate metabolite to human plasma protein is negligible at approximately 3 % while the binding of oseltamivir to human plasma protein is 42%, which is insufficient to cause significant displacement-based drug interactions.20
- Metabolism
Oseltamivir is extensively converted to the active metabolite, oseltamivir carboxylate, by esterases located predominantly in the liver. Oseltamivir carboxylate is not further metabolized. Neither oseltamivir nor oseltamivir carboxylate is a substrate for, or inhibitor of, cytochrome P450 isoforms. No phase 2 conjugates of either compound have been identified in vivo.20,21,15,22
Hover over products below to view reaction partners
- Route of elimination
Following absorption, oseltamivir is more than 90 % eliminated through conversion to oseltamivir carboxylate and subsequent elimination entirely through renal excretion. During clinical studies, less than 20 % of oral radiolabelled dose was found to be eliminated in faeces.20,21,15,22
- Half-life
Plasma concentrations of oseltamivir declined with a half-life of 1 to 3 hours in most subjects after oral administration, although plasma concentrations of oseltamivir carboxylate declined with a half-life of 6 to 10 hours in most subjects after oral administration.20,21
- Clearance
Renal clearance (18.8 l/h) of the drug exceeds glomerular filtration rate (7.5 l/h) indicating that tubular secretion occurs in addition to glomerular filtration.21
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Reports of overdoses with oseltamivir have been received from clinical trials and during postmarketing experience. In the majority of cases reporting overdose, no adverse reactions were reported. Adverse reactions reported following overdose were similar in nature to those observed with therapeutic doses of oseltamivir.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Oseltamivir may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Oseltamivir which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Oseltamivir which could result in a higher serum level. Acetaminophen Oseltamivir may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Oseltamivir which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- Take with or without food. Co-administration with food does not affect pharmacokinetics but may enhance tolerability.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Oseltamivir phosphate 4A3O49NGEZ 204255-11-8 PGZUMBJQJWIWGJ-ONAKXNSWSA-N - Active Moieties
Name Kind UNII CAS InChI Key Oseltamivir acid unknown K6106LV5Q8 187227-45-8 NENPYTRHICXVCS-YNEHKIRRSA-N - Product Images
- International/Other Brands
- Tamiflu
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ebilfumin Capsule 45 mg Oral Actavis Group Ptc Ehf. 2016-09-08 Not applicable EU 
Ebilfumin Capsule 30 mg Oral Actavis Group Ptc Ehf. 2016-09-08 Not applicable EU Ebilfumin Capsule 45 mg Oral Actavis Group Ptc Ehf. 2016-09-08 Not applicable EU Ebilfumin Capsule 75 mg Oral Actavis Group Ptc Ehf. 2016-09-08 Not applicable EU Ebilfumin Capsule 30 mg Oral Actavis Group Ptc Ehf. 2016-09-08 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ach-oseltamivir Phosphate Capsule 45 mg Oral Accord Healthcare Inc Not applicable Not applicable Canada 
Ach-oseltamivir Phosphate Capsule 30 mg Oral Accord Healthcare Inc Not applicable Not applicable Canada Ach-oseltamivir Phosphate Capsule 75 mg Oral Accord Healthcare Inc Not applicable Not applicable Canada Ag-oseltamivir Capsule 45 mg Oral Angita Pharma Inc. Not applicable Not applicable Canada Ag-oseltamivir Capsule 30 mg Oral Angita Pharma Inc. Not applicable Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ENFLUVIR 12 MG/ML ORAL SUSPANSIYON HAZIRLAMAK İÇİN TOZ Oseltamivir (12 mg/ml) Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2013-01-29 Not applicable Turkey 
ENFLUVIR 75 MG KAPSUL, 10 ADET Oseltamivir (75 mg) Capsule Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2013-01-29 Not applicable Turkey
Categories
- ATC Codes
- J05AH02 — Oseltamivir
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Gamma amino acids and derivatives
- Alternative Parents
- Enoate esters / Acetamides / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Dialkyl ethers / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Acetamide / Aliphatic homomonocyclic compound / Alpha,beta-unsaturated carboxylic ester / Amine / Carbonyl group / Carboxamide group / Carboxylic acid ester / Dialkyl ether / Enoate ester / Ether
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- diester, primary amino compound, acetamides, amino acid ester, cyclohexenecarboxylate ester (CHEBI:7798)
- Affected organisms
- Influenza A virus
- Influenza B virus
Chemical Identifiers
- UNII
- 20O93L6F9H
- CAS number
- 196618-13-0
- InChI Key
- VSZGPKBBMSAYNT-RRFJBIMHSA-N
- 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
- IUPAC Name
- ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
- SMILES
- CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1
References
- Synthesis Reference
- US5763483
- General References
- Chokephaibulkit K, Uiprasertkul M, Puthavathana P, Chearskul P, Auewarakul P, Dowell SF, Vanprapar N: A child with avian influenza A (H5N1) infection. Pediatr Infect Dis J. 2005 Feb;24(2):162-6. [Article]
- de Jong MD, Tran TT, Truong HK, Vo MH, Smith GJ, Nguyen VC, Bach VC, Phan TQ, Do QH, Guan Y, Peiris JS, Tran TH, Farrar J: Oseltamivir resistance during treatment of influenza A (H5N1) infection. N Engl J Med. 2005 Dec 22;353(25):2667-72. [Article]
- Kiso M, Mitamura K, Sakai-Tagawa Y, Shiraishi K, Kawakami C, Kimura K, Hayden FG, Sugaya N, Kawaoka Y: Resistant influenza A viruses in children treated with oseltamivir: descriptive study. Lancet. 2004 Aug 28-Sep 3;364(9436):759-65. [Article]
- Ward P, Small I, Smith J, Suter P, Dutkowski R: Oseltamivir (Tamiflu) and its potential for use in the event of an influenza pandemic. J Antimicrob Chemother. 2005 Feb;55 Suppl 1:i5-i21. [Article]
- Cooper NJ, Sutton AJ, Abrams KR, Wailoo A, Turner D, Nicholson KG: Effectiveness of neuraminidase inhibitors in treatment and prevention of influenza A and B: systematic review and meta-analyses of randomised controlled trials. BMJ. 2003 Jun 7;326(7401):1235. doi: 10.1136/bmj.326.7401.1235. [Article]
- Kmietowicz Z: WHO downgrades oseltamivir on drugs list after reviewing evidence. BMJ. 2017 Jun 12;357:j2841. doi: 10.1136/bmj.j2841. [Article]
- Jefferson T, Jones MA, Doshi P, Del Mar CB, Hama R, Thompson MJ, Spencer EA, Onakpoya I, Mahtani KR, Nunan D, Howick J, Heneghan CJ: Neuraminidase inhibitors for preventing and treating influenza in healthy adults and children. Cochrane Database Syst Rev. 2014 Apr 10;(4):CD008965. doi: 10.1002/14651858.CD008965.pub4. [Article]
- Michiels B, Van Puyenbroeck K, Verhoeven V, Vermeire E, Coenen S: The value of neuraminidase inhibitors for the prevention and treatment of seasonal influenza: a systematic review of systematic reviews. PLoS One. 2013;8(4):e60348. doi: 10.1371/journal.pone.0060348. Epub 2013 Apr 2. [Article]
- Ebell MH, Call M, Shinholser J: Effectiveness of oseltamivir in adults: a meta-analysis of published and unpublished clinical trials. Fam Pract. 2013 Apr;30(2):125-33. doi: 10.1093/fampra/cms059. Epub 2012 Sep 20. [Article]
- McQuade B, Blair M: Influenza treatment with oseltamivir outside of labeled recommendations. Am J Health Syst Pharm. 2015 Jan 15;72(2):112-6. doi: 10.2146/ajhp140390. [Article]
- Hsu J, Santesso N, Mustafa R, Brozek J, Chen YL, Hopkins JP, Cheung A, Hovhannisyan G, Ivanova L, Flottorp SA, Saeterdal I, Wong AD, Tian J, Uyeki TM, Akl EA, Alonso-Coello P, Smaill F, Schunemann HJ: Antivirals for treatment of influenza: a systematic review and meta-analysis of observational studies. Ann Intern Med. 2012 Apr 3;156(7):512-24. doi: 10.7326/0003-4819-156-7-201204030-00411. Epub 2012 Feb 27. [Article]
- Louie JK, Yang S, Acosta M, Yen C, Samuel MC, Schechter R, Guevara H, Uyeki TM: Treatment with neuraminidase inhibitors for critically ill patients with influenza A (H1N1)pdm09. Clin Infect Dis. 2012 Nov;55(9):1198-204. doi: 10.1093/cid/cis636. Epub 2012 Jul 26. [Article]
- Toovey S, Prinssen EP, Rayner CR, Thakrar BT, Dutkowski R, Koerner A, Chu T, Sirzen-Zelenskaya A, Britschgi M, Bansod S, Donner B: Post-marketing assessment of neuropsychiatric adverse events in influenza patients treated with oseltamivir: an updated review. Adv Ther. 2012 Oct;29(10):826-48. doi: 10.1007/s12325-012-0050-8. Epub 2012 Oct 2. [Article]
- Toovey S, Rayner C, Prinssen E, Chu T, Donner B, Thakrar B, Dutkowski R, Hoffmann G, Breidenbach A, Lindemann L, Carey E, Boak L, Gieschke R, Sacks S, Solsky J, Small I, Reddy D: Assessment of neuropsychiatric adverse events in influenza patients treated with oseltamivir: a comprehensive review. Drug Saf. 2008;31(12):1097-114. doi: 10.2165/0002018-200831120-00006.. [Article]
- Electronic Medicines Compendium: Tamiflu (oseltamivir phosphate) 30 mg Hard Capsules Monograph [Link]
- Lupin launches US Tamiflu generic amid worst flu season in recent memory: Press Release [Link]
- Dailymed - Oseltamivir (FDA) [Link]
- CDC Influenza Antiviral Medications: Summary for Clinicians [Link]
- Canadian Paediatric Society - The use of antiviral drugs for influenza: Guidance for practitioners [Link]
- Oseltamivir FDA Label [File]
- Oseltamivir EMA Label [File]
- Oseltamivir New Zealand Product Information [File]
- External Links
- Human Metabolome Database
- HMDB0014343
- KEGG Drug
- D00900
- KEGG Compound
- C08092
- PubChem Compound
- 65028
- PubChem Substance
- 46507602
- ChemSpider
- 58540
- BindingDB
- 5025
- 260101
- ChEBI
- 7798
- ChEMBL
- CHEMBL1229
- ZINC
- ZINC000003929508
- Therapeutic Targets Database
- DAP000714
- PharmGKB
- PA450721
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Oseltamivir
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Efficacy of Clarithromycin-Naproxen-Oseltamivir Combination Therapy vs. Oseltamivir Alone for Hospitalised Paediatric Influenza Patients 1 somestatus stop reason just information to hide Not Available Completed Not Available Flu caused by Influenza 1 somestatus stop reason just information to hide Not Available Completed Not Available Prematurity of Fetus 1 somestatus stop reason just information to hide Not Available Completed Prevention Influenza, Human 1 somestatus stop reason just information to hide Not Available Completed Treatment Flu caused by Influenza 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Hoffmann la roche inc
- Packagers
- A-S Medication Solutions LLC
- Diversified Healthcare Services Inc.
- DSM Corp.
- F Hoffmann La Roche Ltd.
- F Hoffmann-La Roche Ltd.
- Nucare Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Redpharm Drug
- Dosage Forms
Form Route Strength Suspension Oral Capsule Oral 98527 MG Capsule Oral 39.410 mg Suspension Oral 6.000 mg Capsule Oral 39.400 mg Capsule, coated Oral 75 mg Powder, for solution Oral 1200 g Granule Granule 30 mg Capsule Oral 30 mg/1 For suspension Oral 6 mg/1mL Suspension Oral 30 mg/1 Suspension Oral 6 mg/1mL Capsule Oral 98528 Mg Capsule Oral 98.500 mg Capsule Oral 75.000 mg Suspension Oral 0.360 g Capsule Oral 45 mg/1 Capsule Oral 75 mg/1 Capsule Oral 98.5 mg Powder, for suspension Oral 12 MG/ML Powder, for suspension Oral 12 mg/1mL Powder, for suspension Oral 6 MG/ML Powder, for suspension Oral 6 mg / mL Powder, for suspension Oral 6 mg/1mL Capsule, gelatin coated 30 mg Capsule, gelatin coated 45 mg Capsule Oral Powder, for suspension Oral 12 mg / mL Capsule Oral 98.53 mg Suspension Oral 0.7884 g Capsule Oral 30 mg Capsule Oral 45 mg Powder 6 mg/1ml Capsule Oral 75 mg - Prices
Unit description Cost Unit Tamiflu 10 30 mg capsule Box 101.54USD box Tamiflu 10 45 mg capsule Box 101.54USD box Tamiflu 10 75 mg capsule Disp Pack 101.54USD disp Tamiflu 12 mg/ml Suspension 51.0USD bottle Tamiflu 30 mg gel capsule 9.76USD gel capsule Tamiflu 45 mg gel capsule 9.76USD gel capsule Tamiflu 75 mg gel capsule 9.76USD gel capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2188835 No 2006-08-08 2016-02-26 Canada US5763483 Yes 1998-06-09 2017-02-23 US 
US5866601 Yes 1999-02-02 2016-08-02 US US5952375 Yes 1999-09-14 2015-08-27 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble Not Available logP 1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.686 mg/mL ALOGPS logP 1.3 ALOGPS logP 1.16 Chemaxon logS -2.7 ALOGPS pKa (Strongest Acidic) 14.03 Chemaxon pKa (Strongest Basic) 9.31 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 90.65 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 84.2 m3·mol-1 Chemaxon Polarizability 34.64 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9156 Blood Brain Barrier - 0.9535 Caco-2 permeable - 0.702 P-glycoprotein substrate Substrate 0.5919 P-glycoprotein inhibitor I Non-inhibitor 0.5415 P-glycoprotein inhibitor II Non-inhibitor 0.9771 Renal organic cation transporter Non-inhibitor 0.9429 CYP450 2C9 substrate Non-substrate 0.9083 CYP450 2D6 substrate Non-substrate 0.8276 CYP450 3A4 substrate Substrate 0.5283 CYP450 1A2 substrate Non-inhibitor 0.8367 CYP450 2C9 inhibitor Non-inhibitor 0.8774 CYP450 2D6 inhibitor Non-inhibitor 0.9174 CYP450 2C19 inhibitor Non-inhibitor 0.6677 CYP450 3A4 inhibitor Non-inhibitor 0.8364 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682 Ames test Non AMES toxic 0.6907 Carcinogenicity Non-carcinogens 0.8863 Biodegradation Not ready biodegradable 0.6191 Rat acute toxicity 2.2695 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9826 hERG inhibition (predictor II) Non-inhibitor 0.9464
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 194.3184649 predictedDarkChem Lite v0.1.0 [M-H]- 178.06537 predictedDeepCCS 1.0 (2019) [M+H]+ 194.5933649 predictedDarkChem Lite v0.1.0 [M+H]+ 180.42337 predictedDeepCCS 1.0 (2019) [M+Na]+ 194.4750649 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.59511 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Influenza A virus (strain A/Chile/1/1983 H1N1)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus...
- Gene Name
- NA
- Uniprot ID
- P11485
- Uniprot Name
- Neuraminidase
- Molecular Weight
- 51874.045 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- McKimm-Breschkin J, Trivedi T, Hampson A, Hay A, Klimov A, Tashiro M, Hayden F, Zambon M: Neuraminidase sequence analysis and susceptibilities of influenza virus clinical isolates to zanamivir and oseltamivir. Antimicrob Agents Chemother. 2003 Jul;47(7):2264-72. [Article]
- Du QS, Wang SQ, Chou KC: Analogue inhibitors by modifying oseltamivir based on the crystal neuraminidase structure for treating drug-resistant H5N1 virus. Biochem Biophys Res Commun. 2007 Oct 19;362(2):525-31. Epub 2007 Aug 13. [Article]
- Wang MZ, Tai CY, Mendel DB: Mechanism by which mutations at his274 alter sensitivity of influenza a virus n1 neuraminidase to oseltamivir carboxylate and zanamivir. Antimicrob Agents Chemother. 2002 Dec;46(12):3809-16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Catalyzes the removal of sialic acid (N-acetylneuraminic acid) moieties from glycoproteins and glycolipids. To be active, it is strictly dependent on its presence in the multienzyme complex. Appears to have a preference for alpha 2-3 and alpha 2-6 sialyl linkage
- Specific Function
- Alpha-sialidase activity
- Gene Name
- NEU1
- Uniprot ID
- Q99519
- Uniprot Name
- Sialidase-1
- Molecular Weight
- 45466.96 Da
References
- Chavas LM, Kato R, Suzuki N, von Itzstein M, Mann MC, Thomson RJ, Dyason JC, McKimm-Breschkin J, Fusi P, Tringali C, Venerando B, Tettamanti G, Monti E, Wakatsuki S: Complexity in influenza virus targeted drug design: interaction with human sialidases. J Med Chem. 2010 Apr 8;53(7):2998-3002. doi: 10.1021/jm100078r. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Exo-alpha-sialidase that catalyzes the hydrolytic cleavage of the terminal sialic acid (N-acetylneuraminic acid, Neu5Ac) of a glycan moiety in the catabolism of glycolipids, glycoproteins and oligosacharides (PubMed:14613940, PubMed:22228546). Recognizes sialyl linkage positions of the glycan moiety as well as the supramolecular organization of the sialoglycoconjugate. Displays preference for alpha-(2->3)-sialylated GD1a and GT1B gangliosides over alpha-(2->8)-sialylated GD1b, in both monomeric forms and micelles. Hydrolyzes monomeric GM1 ganglioside, but has no activity toward the miscellar form (PubMed:14613940). Has lower sialidase activity for glycoproteins such as fetuin and TF/transferrin that carry a mixture of alpha-(2->3) and alpha-(2->6)-sialyl linkages. Cleaves milk oligosaccharide alpha-(2->3)-sialyllactose, but is inactive toward alpha-(2->6)-sialyllactose isomer. Has no activity toward colominic acid, a homomer of alpha-(2->8)-linked Neu5Ac residues (PubMed:14613940)
- Specific Function
- Exo-alpha-(2->3)-sialidase activity
- Gene Name
- NEU2
- Uniprot ID
- Q9Y3R4
- Uniprot Name
- Sialidase-2
- Molecular Weight
- 42253.345 Da
References
- Chavas LM, Kato R, Suzuki N, von Itzstein M, Mann MC, Thomson RJ, Dyason JC, McKimm-Breschkin J, Fusi P, Tringali C, Venerando B, Tettamanti G, Monti E, Wakatsuki S: Complexity in influenza virus targeted drug design: interaction with human sialidases. J Med Chem. 2010 Apr 8;53(7):2998-3002. doi: 10.1021/jm100078r. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Substrate
- Curator comments
- Oseltamivir is extensively converted to the active metabolite, oseltamivir carboxylate, by esterases located predominantly in the liver.
- General Function
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine (PubMed:7980644). Catalyzes the transesterification of cocaine to form cocaethylene (PubMed:7980644). Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate (PubMed:7980644). Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes of 2-arachidonoylglycerol and prostaglandins (PubMed:21049984). Hydrolyzes cellular cholesteryl esters to free cholesterols and promotes reverse cholesterol transport (RCT) by facilitating both the initial and final steps in the process (PubMed:11015575, PubMed:16024911, PubMed:16971496, PubMed:18762277). First of all, allows free cholesterol efflux from macrophages to extracellular cholesterol acceptors and secondly, releases free cholesterol from lipoprotein-delivered cholesteryl esters in the liver for bile acid synthesis or direct secretion into the bile (PubMed:16971496, PubMed:18599737, PubMed:18762277)
- Specific Function
- Carboxylesterase activity
- Gene Name
- CES1
- Uniprot ID
- P23141
- Uniprot Name
- Liver carboxylesterase 1
- Molecular Weight
- 62520.62 Da
References
- Zhu HJ, Markowitz JS: Activation of the antiviral prodrug oseltamivir is impaired by two newly identified carboxylesterase 1 variants. Drug Metab Dispos. 2009 Feb;37(2):264-7. doi: 10.1124/dmd.108.024943. Epub 2008 Nov 20. [Article]
- Shi D, Yang J, Yang D, LeCluyse EL, Black C, You L, Akhlaghi F, Yan B: Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther. 2006 Dec;319(3):1477-84. Epub 2006 Sep 11. [Article]
- Wattanagoon Y, Stepniewska K, Lindegardh N, Pukrittayakamee S, Silachamroon U, Piyaphanee W, Singtoroj T, Hanpithakpong W, Davies G, Tarning J, Pongtavornpinyo W, Fukuda C, Singhasivanon P, Day NP, White NJ: Pharmacokinetics of high-dose oseltamivir in healthy volunteers. Antimicrob Agents Chemother. 2009 Mar;53(3):945-52. doi: 10.1128/AAC.00588-08. Epub 2008 Dec 22. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds and xenobiotics from cells. Transports a range of endogenous molecules that have a key role in cellular communication and signaling, including cyclic nucleotides such as cyclic AMP (cAMP) and cyclic GMP (cGMP), bile acids, steroid conjugates, urate, and prostaglandins (PubMed:11856762, PubMed:12523936, PubMed:12835412, PubMed:12883481, PubMed:15364914, PubMed:15454390, PubMed:16282361, PubMed:17959747, PubMed:18300232, PubMed:26721430). Mediates the ATP-dependent efflux of glutathione conjugates such as leukotriene C4 (LTC4) and leukotriene B4 (LTB4) too. The presence of GSH is necessary for the ATP-dependent transport of LTB4, whereas GSH is not required for the transport of LTC4 (PubMed:17959747). Mediates the cotransport of bile acids with reduced glutathione (GSH) (PubMed:12523936, PubMed:12883481, PubMed:16282361). Transports a wide range of drugs and their metabolites, including anticancer, antiviral and antibiotics molecules (PubMed:11856762, PubMed:12105214, PubMed:15454390, PubMed:17344354, PubMed:18300232). Confers resistance to anticancer agents such as methotrexate (PubMed:11106685)
- Specific Function
- 15-hydroxyprostaglandin dehydrogenase (nad+) activity
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- ATP-binding cassette sub-family C member 4
- Molecular Weight
- 149525.33 Da
References
- Ose A, Ito M, Kusuhara H, Yamatsugu K, Kanai M, Shibasaki M, Hosokawa M, Schuetz JD, Sugiyama Y: Limited brain distribution of [3R,4R,5S]-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (Ro 64-0802), a pharmacologically active form of oseltamivir, by active efflux across the blood-brain barrier mediated by organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistance-associated protein 4 (Mrp4/Abcc4). Drug Metab Dispos. 2009 Feb;37(2):315-21. doi: 10.1124/dmd.108.024018. Epub 2008 Nov 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
- Specific Function
- Dipeptide transmembrane transporter activity
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Ogihara T, Kano T, Wagatsuma T, Wada S, Yabuuchi H, Enomoto S, Morimoto K, Shirasaka Y, Kobayashi S, Tamai I: Oseltamivir (tamiflu) is a substrate of peptide transporter 1. Drug Metab Dispos. 2009 Aug;37(8):1676-81. doi: 10.1124/dmd.109.026922. Epub 2009 May 13. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity)
- Specific Function
- Organic anion transmembrane transporter activity
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Organic anion transporter 3
- Molecular Weight
- 59855.585 Da
References
- Ose A, Ito M, Kusuhara H, Yamatsugu K, Kanai M, Shibasaki M, Hosokawa M, Schuetz JD, Sugiyama Y: Limited brain distribution of [3R,4R,5S]-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (Ro 64-0802), a pharmacologically active form of oseltamivir, by active efflux across the blood-brain barrier mediated by organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistance-associated protein 4 (Mrp4/Abcc4). Drug Metab Dispos. 2009 Feb;37(2):315-21. doi: 10.1124/dmd.108.024018. Epub 2008 Nov 24. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 16, 2024 01:22