Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Fosamprenavir: Difference between pages

{{Short description|Chemical compound}}

| Watchedfields = changed

| verifiedrevid = 461113196

| image = Fosamprenavir structure.svg

| alt =

| image2 = Fosamprenavir ball-and-stick.png

| alt2 =

| USAN = Fosamprenavir calcium

| tradename = Lexiva, Telzir

| Drugs.com = {{drugs.com|monograph|fosamprenavir}}

| pregnancy_AU = B3

| licence_EU = yes

| routes_of_administration = [[Oral administration|By mouth]]

| ATC_prefix = J05

| ATC_suffix = AE07

| legal_CA = Rx-only

| legal_CA_comment = <ref>{{cite web | title=Telzir Product information | website=Health Canada | date=25 April 2012 | url=https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=74692 | access-date=2 October 2022 | archive-date=14 June 2021 | archive-url=https://web.archive.org/web/20210614191654/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=74692 | url-status=live }}</ref>

| legal_UK = POM

| legal_UK_comment = <ref>{{cite web | title=Telzir 700 mg film-coated tablets - Summary of Product Characteristics (SmPC) | website=(emc) | date=22 June 2021 | url=https://www.medicines.org.uk/emc/product/5555 | access-date=2 October 2022 | archive-date=6 December 2021 | archive-url=https://web.archive.org/web/20211206052815/https://www.medicines.org.uk/emc/product/5555 | url-status=live }}</ref>

| legal_US = Rx-only

| legal_US_comment = <ref name="Lexiva FDA label">{{cite web | title=Lexiva- fosamprenavir calcium tablet, film coated Lexiva- fosamprenavir calcium suspension | website=DailyMed | date=1 October 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=24feb9be-32a6-45fd-a896-f3e202edd8a9 | access-date=2 October 2022 | archive-date=29 January 2022 | archive-url=https://web.archive.org/web/20220129105509/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=24feb9be-32a6-45fd-a896-f3e202edd8a9 | url-status=live }}</ref>

| legal_EU = Rx-only

| legal_EU_comment = <ref name="Telzir EPAR">{{cite web | title=Telzir EPAR | website=European Medicines Agency | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/telzir | access-date=2 October 2022 | archive-date=15 May 2021 | archive-url=https://web.archive.org/web/20210515011723/https://www.ema.europa.eu/en/medicines/human/EPAR/telzir | url-status=live }}</ref>

| index2_label = as salt

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 226700-79-4

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 226700-81-8

| PubChem2 = 131535

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank2 = DBSALT001228

| ChemSpiderID2 = 116244

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = ID1GU2627N

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D02497

| KEGG2 = D03835

| ChEBI = 82941

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL2 = 1200734

| NIAID_ChemDB = 082186

| IUPAC_name = {[(2''R'',3''S'')-1-[''N''-(2-methylpropyl)(4-aminobenzene)sulfonamido]-3-({[(3''S'')-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid

| C=25 | H=36 | N=3 | O=9 | P=1 | S=1

| SMILES = O=C(O[C@H]1CCOC1)N[C@@H](Cc2ccccc2)[C@H](OP(=O)(O)O)CN(CC(C)C)S(=O)(=O)c3ccc(N)cc3

| StdInChI2 = 1S/C25H36N3O9PS.Ca/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21;/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32);/q;+2/p-2/t21-,23-,24+;/m0./s1

| StdInChIKey2 = PMDQGYMGQKTCSX-HQROKSDRSA-L

'''Fosamprenavir''' ('''FPV'''), sold under the brand names '''Lexiva''' and '''Telzir''', is a [[medication]] used to treat [[HIV/AIDS]].<ref name="Lexiva FDA label" /><ref name="Telzir EPAR" /> It is a [[prodrug]] of the [[protease inhibitor (pharmacology)|protease inhibitor]] and [[antiretroviral drug]] [[amprenavir]].<ref>{{Cite web |url=https://www.drugs.com/monograph/fosamprenavir.html |title=Fosamprenavir Monograph for Professionals |access-date=2022-10-03 |archive-date=2021-06-28 |archive-url=https://web.archive.org/web/20210628020421/https://www.drugs.com/monograph/fosamprenavir.html |url-status=live }}</ref> It is marketed by [[ViiV Healthcare]] as the [[calcium]] salt.<ref name="Lexiva FDA label" /><ref name="Telzir EPAR" />

Fosamprenavir was approved for medical use in the United States in October 2003,<ref>{{cite web | title=Drug Approval Package: Lexiva (Fosamprenavir Calcium) NDA #021548 | website=U.S. [[Food and Drug Administration]] (FDA) | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-548_Lexiva.cfm | access-date=2 October 2022 | archive-date=15 April 2021 | archive-url=https://web.archive.org/web/20210415193225/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-548_Lexiva.cfm | url-status=live }}</ref> and in the European Union in July 2004.<ref name="Telzir EPAR" /> The human body metabolizes fosamprenavir in order to form amprenavir, which is the active ingredient.<ref name="Lexiva FDA label" />

A head-to-head study with [[lopinavir]] showed the two drugs to have comparable potency, but patients on fosamprenavir tended to have a higher serum cholesterol.<ref>{{cite journal | vauthors = Eron J, Yeni P, Gathe J, Estrada V, DeJesus E, Staszewski S, Lackey P, Katlama C, Young B, Yau L, Sutherland-Phillips D, Wannamaker P, Vavro C, Patel L, Yeo J, Shaefer M | display-authors = 6 | title = The KLEAN study of fosamprenavir-ritonavir versus lopinavir-ritonavir, each in combination with abacavir-lamivudine, for initial treatment of HIV infection over 48 weeks: a randomised non-inferiority trial | journal = Lancet | volume = 368 | issue = 9534 | pages = 476–82 | date = August 2006 | pmid = 16890834 | doi = 10.1016/S0140-6736(06)69155-1 | s2cid = 33612672 }}</ref>

==Medical uses==

Fosamprenavir is used for the treatment of [[HIV-1]] infections, typically but not necessarily in combination with low-dose [[ritonavir]] or other antiviral drugs.<ref name="Austria-Codex">{{cite book|title=Austria-Codex| veditors = Jasek W |publisher=Österreichischer Apothekerverlag|location=Vienna|year=2007|edition=62nd|isbn=978-3-85200-181-4|pages=8009–17|language=German}}</ref><ref>{{cite report | work = [[Drugs.com]] | title = Lexiva | id = {{drugs.com|monograph|lexiva}}}}</ref>

==Adverse effects==

The most common adverse effect is diarrhea. Other common side effects include [[headache]], dizziness and exanthema, which is usually transient. Severe allergic reactions ([[Stevens–Johnson syndrome]]) are rare.<ref name="Austria-Codex" />

== Interactions ==

Amprenavir (the active metabolite of fosamrenavir, which is found in blood plasma, liver and other organs) is metabolized via the liver enzyme [[CYP3A4]] and also weakly inhibits this enzyme. This means that combination with drugs that are also metabolized by CYP3A4 can increase their plasma concentrations and thus side effects; and combination with drugs that inhibit CYP3A4 can increase amprenavir concentrations.<ref name="Austria-Codex" />

When combining fosamprenavir with low doses of the CYP3A4 inhibitor ritonavir, this interaction is intended as it allows for application of lower fosamprenavir doses.<ref name="Austria-Codex" />

==Pharmacology==

Fosamprenavir is quickly activated to amprenavir, even before it reaches the circulation. Amprenavir is a HIV [[protease inhibitor (pharmacology)|protease inhibitor]].<ref name="Austria-Codex" />

[[File:3nu3 478.png|thumb|left|[[HIV-1 protease]] dimer with amprenavir (sticks) bound in the active site. PDB entry {{PDBe|3nu3}}<ref>{{cite journal | vauthors = Shen CH, Wang YF, Kovalevsky AY, Harrison RW, Weber IT | title = Amprenavir complexes with HIV-1 protease and its drug-resistant mutants altering hydrophobic clusters | journal = The FEBS Journal | volume = 277 | issue = 18 | pages = 3699–714 | date = September 2010 | pmid = 20695887 | pmc = 2975871 | doi = 10.1111/j.1742-4658.2010.07771.x }}</ref>]]

== References ==

{{reflist}}

== External links ==

* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/fosamprenavir | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Fosamprenavir }}

* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/fosamprenavir%20calcium | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Fosamprenavir calcium }}

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[[Category:Carbamates]]

[[Category:CYP3A4 inhibitors]]

[[Category:Drugs developed by GSK plc]]

[[Category:HIV protease inhibitors]]

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[[Category:Sulfonamides]]

[[Category:Tetrahydrofurans]]