Oseltamivir — разлика између измена

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{{Drugbox-lat
{{Drugbox-lat
| Verifiedfields =
| IUPAC_name = etil (-{3R,4R,5S}-)-5-amino-4-acetamido-3-(pentan-3-iloksi)cikloheks-1-en-1-karboksilat
| Watchedfields =
| image = Oseltamivir.svg
| verifiedrevid = 459589411
| width =
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| alt =
| IUPAC_name = etil (-{3R,4R,5S}-)-5-amino-4-acetamido-3-(pentan-3-iloksi)-cikloheks-1-en-1-karboksilat
| image2 = Oseltamivir-3D-balls.png
| image = Oseltamivir.svg
| width2 =
| image2 = Oseltamivir-3D-balls.png
| alt2 =
| drug_name = Oseltamivir
| caption =


<!-- Clinical data -->
<!--Clinical data-->
| tradename =
| pronounce =
| tradename = Tamiflu<ref>{{cite web|title=Tamiflu - Drugs.com|url=https://www.drugs.com/international/tamiflu.html|website=www.drugs.com|accessdate=16. 1. 2017}}</ref>
| Drugs.com = {{drugs.com-lat|monograph|Oseltamivir}}
| Drugs.com = {{drugs.com|monograph|oseltamivir-phosphate}}
| MedlinePlus =
| MedlinePlus = a699040
| licence_EU =
| licence_US =
| pregnancy_AU = B1
| DailyMedID =
| pregnancy_US = C
| legal_AU = Schedule 4
| pregnancy_AU =
| legal_UK = POM
| pregnancy_US =
| legal_US = Rx-only
| pregnancy_category=
| routes_of_administration = oralno
| legal_AU =
| licence_US = Oseltamivir
| legal_CA =
| DailyMedID = 48517
| legal_UK =
| legal_US =
| legal_status =
| dependency_liability =
| routes_of_administration = Oralno


<!-- Pharmacokinetic data -->
<!--Pharmacokinetic data-->
| bioavailability = >80%<ref name = PK>{{cite journal|last=Davies|first=BE|title=Pharmacokinetics of oseltamivir: an oral antiviral for the treatment and prophylaxis of influenza in diverse populations.|journal=The Journal of antimicrobial chemotherapy|date= 2010|volume=65 Suppl 2|pages=ii5-ii10|doi=10.1093/jac/dkq015|pmid=20215135|url=http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2835511/pdf/dkq015.pdf|format=PDF|pmc=2835511}}</ref>
| bioavailability =
| protein_bound =
| protein_bound = 42% (roditeljski lek), 3% (aktivni metabolit)<ref name = PK />
| metabolism =
| metabolism = [[Jetra|Hepatički]], do oseltamivir karboksilata<ref name = PK />
| elimination_half-life = 1 - 3 sata
| elimination_half-life = 1-3 sata, 6-10 sata (aktivni metabolit)<ref name = PK />
| excretion =
| excretion = Urin (>90% oseltamivir karboksilat), izmet<ref name = PK />


<!-- Identifiers -->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|}}
| CAS_number_Ref = {{cascite|correct|}}
| CAS_number = 204255-11-8
| CAS_number = 204255-11-8
| ATC_prefix = J05
| CAS_supplemental =
| ATC_suffix = AH02
| ATCvet =
| PubChem = 65028
| ATC_prefix = J05
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ATC_suffix = AH02
| DrugBank = DB00198
| ATC_supplemental =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| PubChem = 65028
| ChemSpiderID = 58540
| PubChemSubstance = 46507602
| UNII_Ref = {{fdacite|correct|FDA}}
| IUPHAR_ligand =
| UNII = 20O93L6F9H
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| DrugBank = DB00198
| KEGG = D08306
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChemSpiderID = 58540
| ChEBI = 7798
| UNII_Ref = {{fdacite|correct|FDA}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| UNII =
| ChEMBL = 1229
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C08093
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 7798
| synonyms =


<!-- Chemical data -->
<!--Chemical data-->
|C=16 |H=28 |N=2 |O=4
| C=16 | H=28 | N=2 | O=4
| molecular_weight = 312.4045
| molecular_weight = 312.4 g/mol
| smiles = CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1
| smiles = O=C(OCC)/C1=C/[C@@H](OC(CC)CC)[C@H](NC(=O)C)[C@@H](N)C1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_comment =
| StdInChIKey = VSZGPKBBMSAYNT-RRFJBIMHSA-N
| StdInChIKey = VSZGPKBBMSAYNT-RRFJBIMHSA-N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| density =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| specific_rotation =
| sec_combustion =
}}
}}
<!-- Definition and recommendations -->
'''Oseltamivir''' je acetamido [[cikloheksen]] koji je [[Strukturni analog|strukturni homolog]] [[Sijalinska kiselina|sijalinske kiseline]] i inhibira [[neuraminidaza|neuraminidazu]].<ref>-{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. [[PubMed|PMID]] [http://www.ncbi.nlm.nih.gov/pubmed/15702046 15702046]}-</ref><ref>-{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. [[PubMed|PMID]] [http://www.ncbi.nlm.nih.gov/pubmed/16371632 16371632]}-</ref><ref>-{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. [[PubMed|PMID]] [http://www.ncbi.nlm.nih.gov/pubmed/15337401 15337401]}-</ref><ref>-{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. [[PubMed|PMID]] [http://www.ncbi.nlm.nih.gov/pubmed/15709056 15709056]}-</ref><ref>{{cite journal |title = DrugBank 3.0: a comprehensive resource for omics research on drugs |vauthors=Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS |journal = Nucleic Acids Res. |year = 2011 |volume = 39 |issue = Database issue |pages = D1035-41 | pmid =21059682}}</ref><ref>{{cite journal |title = DrugBank: a knowledgebase for drugs, drug actions and drug targets |author = Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M (Nucleic Acids Res) |year = 2008 |volume = 36 |issue = Database issue |pages = D901-6 |pmid = 18048412}}</ref>
'''Oseltamivir''', koji se prodaje pod imenom '''Tamiflu''', je [[antiviralni lek]] koji se koristi za tretiranje i prevenciju [[influenza A virus|influenza A]] i [[Influenzavirus B|influenza B]] (gripa).<ref name=AHFS2017/> Mnoge medicinske organizacije preporučuju ovaj lek za ljudi koji imaju komplikacije ili su izloženi visokom riziku od komplikacija u toku od 48 sati od prvih simptoma infekcije.<ref name=CDC2014up /> Ovaj lek se preporučuje za sprečavanje infekcije kod tih osova s visokim rizikom, ali ne i kod opšte populacije.<ref name=CDC2014up /> CDC preporučuje da lekari korste svoju diskreciju kod onih sa niskim rizikom u toku 48 sati nakon prvih simptoma infekcije.<ref name=CDC2014up>{{cite web|title=CDC Online Newsroom - "Have You Heard?" Archive: 2014 - Influenza A Variant Virus|url=http://www.cdc.gov/media/haveyouheard/stories/Influenza_antiviral2.html|website=www.cdc.gov|accessdate=16. 1. 2017|date=10. 4. 2014}}</ref><ref name=ECDC2014>{{cite web |author=European Centre for Disease Prevention and Control|url=http://www.ecdc.europa.eu/en/activities/sciadvice/_layouts/forms/Review_DispForm.aspx?List=a3216f4c-f040-4f51-9f77-a96046dbfd72&ID=764 |title=New and updated evaluations of neuraminidase inhibitors for preventing and treating influenza published|date=2. 6. 2014}}</ref><ref name=NICE2009>{{cite web|title=Amantadine, oseltamivir and zanamivir for the treatment of influenza|url=https://www.nice.org.uk/guidance/TA168| website=www.nice.org.uk|publisher=NICE|accessdate=16. 1. 2017|date=25. 2. 2009}}</ref> Lek se uzima oralno, bilo u vidu pilule ili tečnosti.<ref name=AHFS2017>{{cite web|title=Oseltamivir Phosphate| url=https://www.drugs.com/monograph/oseltamivir-phosphate.html| publisher=The American Society of Health-System Pharmacists|accessdate= 8. 1. 2017}}</ref>

<!-- Evidence -->
Preporuke oseltamivira su kontroverznie, a isto važi i za kritike preporuka.<ref name=CDC2014up /><ref name=IDSA2014>{{cite web |url=http://www.idsociety.org/Influenza_Statement.aspx |title=IDSA : IDSA Continues to Recommend Antivirals for Influenza |format= |work= |accessdate= 24. 4. 2014}}</ref><ref name=Brownlee2013>{{cite web | url=https://www.theatlantic.com/health/archive/2013/02/tamiflu-myth-and-misconception/273167/ | title=Tamiflu: Myth and Misconception | work=The Atlantic | date=19. 2. 2013 | accessdate=7. 12. 2014 | author=Brownlee, Shannon}}</ref><ref name=Butler2014 /> Godine 2014. [[Kohrannov pregled]] je izveo zaključak da oseltamivir ne redukuju broj hospitalizacija, i da ne postoji evidencija redukcije komplikacija influenze.<ref name=Butler2014>{{cite journal|last1=Butler|first1=Declan|title=Tamiflu report comes under fire| journal=Nature| volume=508|issue=7497| year=2014| pages=439–440| doi=10.1038/508439a|pmid=24759392}}</ref> Dve [[Metaanaliza|metaanalize]] su došle do zaključka da koristi kod onih koji su inače zdravi ne prevazilaze rizike.<ref name=Mich2013>{{cite journal|last=Coenen|first=B|author2=Van Puyenbroeck, K |author3=Verhoeven, V |author4=Vermeire, E |author5=Coenen, S|title=The value of neuraminidase inhibitors for the prevention and treatment of seasonal influenza: a systematic review of systematic reviews|journal=PLoS ONE|year=2013|volume=8|issue=4|pages=e60348|pmid=23565231|bibcode=2013PLoSO...860348M|doi=10.1371/journal.pone.0060348|pmc=3614893|editor1-last=Jefferson|editor1-first=Tom}}</ref><ref name=Ebe2013 /> Te studije su isto tako našle malo dokaza da tretman menja rizik od hospitalizacije ili smrti kod populacije sa visokim rizikom.<ref name=Mich2013/><ref name=Ebe2013>{{cite journal|last=Ebell|first=MH|author2=Call, M |author3=Shinholser, J |title=Effectiveness of oseltamivir in adults: a meta-analysis of published and unpublished clinical trials|journal=Family practice|date=2013 |volume=30|issue=2 |pages=125–33|pmid=22997224 |doi=10.1093/fampra/cms059}}</ref> Međutim, jedna druga metaanaliza je došla do zaključka da je oseltamivir efektivan u prevenciji influenze kod individua i na nivou domaćinstva.<ref>{{cite journal|last1=Okoli|first1=George N.|last2=Otete|first2=Harmony E.|last3=Beck|first3=Charles R.|last4=Nguyen-Van-Tam|first4=Jonathan S.|last5=Schmidt|first5=Robert Lane|title=Use of Neuraminidase Inhibitors for Rapid Containment of Influenza: A Systematic Review and Meta-Analysis of Individual and Household Transmission Studies|journal=PLoS ONE|date=9. 12. 2014 |volume=9|issue=12|pages=e113633|doi=10.1371/journal.pone.0113633|pmid=25490762|pmc=4260958}}</ref>

<!-- Side effects -->
Uobičajeni neželjeni efekti su [[povraćanje]], [[dijareja]], glavobolja, i problemi sa spavanjem.<ref name=AHFS2017/> Druge nuspojave mogu da obuhvate [[Душевна болест|psihijatrijske simptome]] i [[Епилептички напад|epileptičke napade]].<ref name=AHFS2017/><ref name=Cochrane2012>{{cite journal |vauthors=Wang K, Shun-Shin M, Gill P, Perera R, Harnden A |title=Neuraminidase inhibitors for preventing and treating influenza in children (published trials only) |journal=Cochrane Database Syst Rev |volume=4 |issue= |pages=CD002744 |year=2012 |pmid=22513907 |doi=10.1002/14651858.CD002744.pub4 |editor1-last=Harnden |editor1-first=Anthony }}</ref><ref name=Jeff2014>{{cite journal| last1=Jefferson| first1=T|last2=Jones| first2=M| last3=Doshi| first3=P| last4=Spencer|first4=EA|last5=Onakpoya|first5=I|last6=Heneghan|first6=CJ|title=Oseltamivir for influenza in adults and children: systematic review of clinical study reports and summary of regulatory comments.|journal=BMJ (Clinical research ed.)|date= 9. 4. 2014| volume=348| pages=g2545| pmid=24811411|pmc=3981975|doi=10.1136/bmj.g2545}}</ref> U Sjedinjenim Državama ovaj lek se preporučuje za infekcije influenzom tokom trudnoće.<ref name=Preg2017/> Lek je koristio mali broj trudnih žena bez znakova problema.<ref name=Preg2017>{{cite web|title=Oseltamivir (Tamiflu) Use During Pregnancy|url=https://www.drugs.com/pregnancy/oseltamivir.html|website=www.drugs.com|accessdate=16. 1. 2017}}</ref> Podešavanje doze je neophodno kod onih koji imaju probleme s bubrezima.<ref name=AHFS2017/>

<!-- History, society and culture -->
Oseltamivir je bio odobren za medicinsku upotrebu u SAD 1999. godine.<ref name=AHFS2017/> On je bio prvi [[neuraminidazni inhibitor]] koji je oralno dostupan.<ref>{{cite journal|last=Agrawal|first=R|author2=Rewatkar, PV |author3=Kokil, GR |author4=Verma, A |author5= Kalra, A |title=Oseltamivir: a first line defense against swine flu.|journal=Medicinal chemistry (Shariqah (United Arab Emirates))|date= 2010|volume=6|issue=4|pages=247–51|pmid=20843284}}</ref> On je na [[Spisak esencijalnih lekova Svetske zdravstvene organizacije|spisaku esencijalnih lekova Svetske zdravstvene organizacije]], najefektivnijih i najbezbednijih lekova neophodnih [[zdravstvo|zdravstvenim sistemima]].<ref name=WHO19th>{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|work=World Health Organization|accessdate=8. 12. 2016|date= 2015}}</ref> [[Generički lek|Generička verzija]] je odobrena u SAD 2016.<ref>{{cite web|title=The FDA approves first generic version of widely used influenza drug, Tamiflu|url=http://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm514854.htm|website=FDA|accessdate=6. 8. 2016|date=4. 8. 2016}}</ref> Godine 2014. veleprodajni trošak u zemljama u razvoju je bio oko {{US$|4.27}} na dan.<ref>{{cite web|title=Oseltamivir|url=http://erc.msh.org/dmpguide/resultsdetail.cfm?language=english&code=OSE75T&s_year=2014&year=2014&str=75%20mg&desc=Oseltamivir&pack=new&frm=TAB-CAP&rte=PO&class_code2=06%2E4%2E3%2E&supplement=&class_name=%2806%2E4%2E3%2E%29Other%20antivirals%3Cbr%3E|website=International Drug Price Indicator Guide|accessdate=30. 7. 2016}}</ref> Decembera 2016, trošak kursa tretmana je US$ 138.70 u SAD.<ref>{{cite web|title=NADAC as of 2016-12-07 {{!}} Data.Medicaid.gov|url=https://data.medicaid.gov/Drug-Prices/NADAC-as-of-2016-12-07/ry9m-tx78|website=Centers for Medicare and Medicaid Services|accessdate=16. 1. 2017}}</ref>

'''Oseltamivir''' je acetamido [[cikloheksen]] koji je [[Strukturni analog|strukturni homolog]] [[Sijalinska kiselina|sijalinske kiseline]] i inhibira [[neuraminidaza|neuraminidazu]].<ref>-{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. [[PubMed|PMID]] [http://www.ncbi.nlm.nih.gov/pubmed/15702046 15702046]}-</ref><ref>-{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. [[PubMed|PMID]] [http://www.ncbi.nlm.nih.gov/pubmed/16371632 16371632]}-</ref><ref>-{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. [[PubMed|PMID]] [http://www.ncbi.nlm.nih.gov/pubmed/15337401 15337401]}-</ref><ref>-{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. [[PubMed|PMID]] [http://www.ncbi.nlm.nih.gov/pubmed/15709056 15709056]}-</ref><ref>{{cite journal |title = DrugBank 3.0: a comprehensive resource for omics research on drugs |vauthors=Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS |journal = Nucleic Acids Res. |year = 2011 |volume = 39 |issue = Database issue |pages = D1035-41 | pmid =21059682}}</ref><ref>{{cite journal |title = DrugBank: a knowledgebase for drugs, drug actions and drug targets |vauthors = Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M |journal = Nucleic Acids Res |year = 2008 |volume = 36 |issue = Database issue |pages = D901-6 |pmid = 18048412}}</ref>


== Reference ==
== Reference ==
{{reflist|2}}
{{reflist|2}}

== Literatura ==
* {{cite news | author = Pollack, Andrew | title = Is Bird Flu Drug Really So Vexing? Debating the Difficulty of Tamiflu | work = [[The New York Times]] | date = 5. 11. 2005 | url = https://www.nytimes.com/2005/11/05/business/05tamiflu.html }}
* {{cite journal | first=Y. K. | first2=K. Y.|title=Avian influenza virus infections in humans|journal=Chest|volume=129|issue=1|pages=156–168| date= 2006 |pmid=16424427|doi=10.1378/chest.129.1.156| last1=Wong| last2=Yuen}}
* {{Cite journal| first1 = J. C.| first2 = K. M.| first3 = M. J.| first4 = M. W.| first5 = H. H.| last1 = Rohloff| first6 = D. E.| first7 = W.| first8 = M. S.| first9 = L. R.| last10 = Prisbe | first10 = E. J.| last11 = Schultze | first11 = L. M.| last12 = Yu | first12 = R. H.| last13 = Zhang | first13 = L. | title = Practical Total Synthesis of the Anti-Influenza Drug GS-4104 | journal = The Journal of Organic Chemistry | volume = 63| issue = 13 | pages = 4545–4550 | year = 1998 | doi = 10.1021/jo980330q| last2 = Kent| last3 = Postich| last4 = Becker| last5 = Chapman| last6 = Kelly| last7 = Lew| last8 = Louie| last9 = McGee}}
* {{cite journal | last1=Karpf | first=T. R. | last2=Trussardi | first2=R.|title=New, azide-free transformation of epoxides into 1,2-diamino compounds: synthesis of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu)|journal=J. Org. Chem.|volume=66|issue=6|pages=2044–2051| date= 2001 |pmid=11300898|doi=10.1021/jo005702l}}
* {{Cite journal| first1 = S.| first2 = P.| first3 = H.| first4 = M.| first5 = R.| first6 = B.| first7 = U. | title = The Synthetic Development of the Anti-Influenza Neuraminidase Inhibitor Oseltamivir Phosphate (Tamiflu<sup>®</sup>): A Challenge for Synthesis & Process Research | journal = CHIMIA International Journal for Chemistry | volume = 58| issue = 9| last1 = Abrecht | pages = 621–629 | year = 2004 | doi = 10.2533/000942904777677605| last2 = Harrington| last3 = Iding| last4 = Karpf| last5 = Trussardi| last6 = Wirz| last7 = Zutter}}
* {{cite journal | last1=Yeung | first=H. S. | last2=Hong | first2=S. | last3=Corey | first3=E. J.|title=A short enantioselective pathway for the synthesis of the anti-influenza neuramidase inhibitor oseltamivir from 1,3-butadiene and acrylic acid|journal=J. Am. Chem. Soc.|volume=128|issue=19|pages=6310–6311| date= 2006 |pmid=16683783|doi=10.1021/ja0616433}}
* {{Cite journal | pmid = 1951305 | date= 1991 | last1 = Tse | first1 = N. | last2 = Cederbaum | first2 = S. | last3 = Glaspy | first3 = J. A. | title = Hyperammonemia following allogeneic bone marrow transplantation | volume = 38 | issue = 2 | pages = 140–141 | issn = 0361-8609 | journal = American journal of hematology | url = http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+7664-41-7 | format = Free full text | doi = 10.1002/ajh.2830380213}}


== Spoljašnje veze ==
== Spoljašnje veze ==
Ред 88: Ред 87:
{{Commonscat-lat|Oseltamivir}}
{{Commonscat-lat|Oseltamivir}}
* [http://www.drugbank.ca/drugs/DB00198 -{Oseltamivir}-]
* [http://www.drugbank.ca/drugs/DB00198 -{Oseltamivir}-]
* {{Official website|http://www.tamiflu.com/}}
* [http://www.nlm.nih.gov/medlineplus/druginfo/meds/a699040.html MedlinePlus Drug Information: oseltamivir (systemic)] –Last Revised – 05/01/2009 Advice for the Patient
* [http://www.pharmasquare.org/flash/Tamiflu.html Pharmasquare – Tamiflu Mode of Action] – [[Macromedia Flash|Flash]] animation showing the mode of action of oseltamivir
* [http://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm107838.htm FDA information page on oseltamivir]
* [http://www.niaid.nih.gov/factsheets/fludrugs.htm Flu Drugs FAQ] – U.S. National Institute of Allergy and Infectious Diseases
* Reto U. Schneider: [http://www.nzzfolio.ch/www/d80bd71b-b264-4db4-afd0-277884b93470/showarticle/52e8d9fe-7076-4440-998f-b0afe1d1dd31.aspx The race to develop GS4104] – A comprehensive feature story about the development of Tamiflu published in January 2004 in NZZ-Folio, the magazine of the daily Neue Zürcher Zeitung in Switzerland (translated from German).


{{Medicinsko upozorenje-lat}}
{{Medicinsko upozorenje-lat}}

Верзија на датум 3. мај 2017. у 21:28

Oseltamivir
IUPAC ime
etil (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-iloksi)-cikloheks-1-en-1-karboksilat
Klinički podaci
Prodajno imeTamiflu[1]
Drugs.comМонографија
MedlinePlusa699040
Podaci o licenci
Kategorija trudnoće
  • AU: B1
  • US: C (Mogući rizik)
Način primeneoralno
Pravni status
Pravni status
  • AU: S4 (Prescription only)
  • UK: POM (Samo na recepat)
  • US: ℞-only
Farmakokinetički podaci
Bioraspoloživost>80%[2]
Vezivanje proteina42% (roditeljski lek), 3% (aktivni metabolit)[2]
MetabolizamHepatički, do oseltamivir karboksilata[2]
Poluvreme eliminacije1-3 sata, 6-10 sata (aktivni metabolit)[2]
IzlučivanjeUrin (>90% oseltamivir karboksilat), izmet[2]
Identifikatori
CAS broj204255-11-8 ДаY
ATC kodJ05AH02 (WHO)
PubChemCID 65028
DrugBankDB00198 ДаY
ChemSpider58540 ДаY
UNII20O93L6F9H ДаY
KEGGD08306 ДаY
ChEBICHEBI:7798 ДаY
ChEMBLCHEMBL1229 ДаY
Hemijski podaci
FormulaC16H28N2O4
Molarna masa312.4 g/mol
  • O=C(OCC)/C1=C/[C@@H](OC(CC)CC)[C@H](NC(=O)C)[C@@H](N)C1
  • 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 ДаY
  • Key:VSZGPKBBMSAYNT-RRFJBIMHSA-N ДаY

Oseltamivir, koji se prodaje pod imenom Tamiflu, je antiviralni lek koji se koristi za tretiranje i prevenciju influenza A i influenza B (gripa).[3] Mnoge medicinske organizacije preporučuju ovaj lek za ljudi koji imaju komplikacije ili su izloženi visokom riziku od komplikacija u toku od 48 sati od prvih simptoma infekcije.[4] Ovaj lek se preporučuje za sprečavanje infekcije kod tih osova s visokim rizikom, ali ne i kod opšte populacije.[4] CDC preporučuje da lekari korste svoju diskreciju kod onih sa niskim rizikom u toku 48 sati nakon prvih simptoma infekcije.[4][5][6] Lek se uzima oralno, bilo u vidu pilule ili tečnosti.[3]

Preporuke oseltamivira su kontroverznie, a isto važi i za kritike preporuka.[4][7][8][9] Godine 2014. Kohrannov pregled je izveo zaključak da oseltamivir ne redukuju broj hospitalizacija, i da ne postoji evidencija redukcije komplikacija influenze.[9] Dve metaanalize su došle do zaključka da koristi kod onih koji su inače zdravi ne prevazilaze rizike.[10][11] Te studije su isto tako našle malo dokaza da tretman menja rizik od hospitalizacije ili smrti kod populacije sa visokim rizikom.[10][11] Međutim, jedna druga metaanaliza je došla do zaključka da je oseltamivir efektivan u prevenciji influenze kod individua i na nivou domaćinstva.[12]

Uobičajeni neželjeni efekti su povraćanje, dijareja, glavobolja, i problemi sa spavanjem.[3] Druge nuspojave mogu da obuhvate psihijatrijske simptome i epileptičke napade.[3][13][14] U Sjedinjenim Državama ovaj lek se preporučuje za infekcije influenzom tokom trudnoće.[15] Lek je koristio mali broj trudnih žena bez znakova problema.[15] Podešavanje doze je neophodno kod onih koji imaju probleme s bubrezima.[3]

Oseltamivir je bio odobren za medicinsku upotrebu u SAD 1999. godine.[3] On je bio prvi neuraminidazni inhibitor koji je oralno dostupan.[16] On je na spisaku esencijalnih lekova Svetske zdravstvene organizacije, najefektivnijih i najbezbednijih lekova neophodnih zdravstvenim sistemima.[17] Generička verzija je odobrena u SAD 2016.[18] Godine 2014. veleprodajni trošak u zemljama u razvoju je bio oko 4,27 долара na dan.[19] Decembera 2016, trošak kursa tretmana je US$ 138.70 u SAD.[20]

Oseltamivir je acetamido cikloheksen koji je strukturni homolog sijalinske kiseline i inhibira neuraminidazu.[21][22][23][24][25][26]

Reference

  1. ^ „Tamiflu - Drugs.com”. www.drugs.com. Приступљено 16. 1. 2017. 
  2. ^ а б в г д Davies, BE (2010). „Pharmacokinetics of oseltamivir: an oral antiviral for the treatment and prophylaxis of influenza in diverse populations.” (PDF). The Journal of antimicrobial chemotherapy. 65 Suppl 2: ii5—ii10. PMC 2835511 Слободан приступ. PMID 20215135. doi:10.1093/jac/dkq015. 
  3. ^ а б в г д ђ „Oseltamivir Phosphate”. The American Society of Health-System Pharmacists. Приступљено 8. 1. 2017. 
  4. ^ а б в г „CDC Online Newsroom - "Have You Heard?" Archive: 2014 - Influenza A Variant Virus”. www.cdc.gov. 10. 4. 2014. Приступљено 16. 1. 2017. 
  5. ^ European Centre for Disease Prevention and Control (2. 6. 2014). „New and updated evaluations of neuraminidase inhibitors for preventing and treating influenza published”. 
  6. ^ „Amantadine, oseltamivir and zanamivir for the treatment of influenza”. www.nice.org.uk. NICE. 25. 2. 2009. Приступљено 16. 1. 2017. 
  7. ^ „IDSA : IDSA Continues to Recommend Antivirals for Influenza”. Приступљено 24. 4. 2014. 
  8. ^ Brownlee, Shannon (19. 2. 2013). „Tamiflu: Myth and Misconception”. The Atlantic. Приступљено 7. 12. 2014. 
  9. ^ а б Butler, Declan (2014). „Tamiflu report comes under fire”. Nature. 508 (7497): 439—440. PMID 24759392. doi:10.1038/508439a. 
  10. ^ а б Coenen, B; Van Puyenbroeck, K; Verhoeven, V; Vermeire, E; Coenen, S (2013). Jefferson, Tom, ур. „The value of neuraminidase inhibitors for the prevention and treatment of seasonal influenza: a systematic review of systematic reviews”. PLoS ONE. 8 (4): e60348. Bibcode:2013PLoSO...860348M. PMC 3614893 Слободан приступ. PMID 23565231. doi:10.1371/journal.pone.0060348. 
  11. ^ а б Ebell, MH; Call, M; Shinholser, J (2013). „Effectiveness of oseltamivir in adults: a meta-analysis of published and unpublished clinical trials”. Family practice. 30 (2): 125—33. PMID 22997224. doi:10.1093/fampra/cms059. 
  12. ^ Okoli, George N.; Otete, Harmony E.; Beck, Charles R.; Nguyen-Van-Tam, Jonathan S.; Schmidt, Robert Lane (9. 12. 2014). „Use of Neuraminidase Inhibitors for Rapid Containment of Influenza: A Systematic Review and Meta-Analysis of Individual and Household Transmission Studies”. PLoS ONE. 9 (12): e113633. PMC 4260958 Слободан приступ. PMID 25490762. doi:10.1371/journal.pone.0113633. 
  13. ^ Wang K, Shun-Shin M, Gill P, Perera R, Harnden A (2012). Harnden A, ур. „Neuraminidase inhibitors for preventing and treating influenza in children (published trials only)”. Cochrane Database Syst Rev. 4: CD002744. PMID 22513907. doi:10.1002/14651858.CD002744.pub4. 
  14. ^ Jefferson, T; Jones, M; Doshi, P; Spencer, EA; Onakpoya, I; Heneghan, CJ (9. 4. 2014). „Oseltamivir for influenza in adults and children: systematic review of clinical study reports and summary of regulatory comments.”. BMJ (Clinical research ed.). 348: g2545. PMC 3981975 Слободан приступ. PMID 24811411. doi:10.1136/bmj.g2545. 
  15. ^ а б „Oseltamivir (Tamiflu) Use During Pregnancy”. www.drugs.com. Приступљено 16. 1. 2017. 
  16. ^ Agrawal, R; Rewatkar, PV; Kokil, GR; Verma, A; Kalra, A (2010). „Oseltamivir: a first line defense against swine flu.”. Medicinal chemistry (Shariqah (United Arab Emirates)). 6 (4): 247—51. PMID 20843284. 
  17. ^ „WHO Model List of Essential Medicines (19th List)” (PDF). World Health Organization. 2015. Приступљено 8. 12. 2016. 
  18. ^ „The FDA approves first generic version of widely used influenza drug, Tamiflu”. FDA. 4. 8. 2016. Приступљено 6. 8. 2016. 
  19. ^ „Oseltamivir”. International Drug Price Indicator Guide. Приступљено 30. 7. 2016. 
  20. ^ „NADAC as of 2016-12-07 | Data.Medicaid.gov”. Centers for Medicare and Medicaid Services. Приступљено 16. 1. 2017. 
  21. ^ 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. PMID 15702046
  22. ^ 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. PMID 16371632
  23. ^ 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. PMID 15337401
  24. ^ 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. PMID 15709056
  25. ^ Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS (2011). „DrugBank 3.0: a comprehensive resource for omics research on drugs”. Nucleic Acids Res. 39 (Database issue): D1035—41. PMID 21059682. 
  26. ^ Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M (2008). „DrugBank: a knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Res. 36 (Database issue): D901—6. PMID 18048412. 

Literatura

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