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Revision as of 14:24, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456679448 of page Fosamprenavir for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 05:04, 22 January 2024 edit Citation bot (talk | contribs)Bots5,390,065 edits Altered title. | Use this bot. Report bugs. | Suggested by Abductive | Category:Multiple chemicals in Infobox drug | #UCB_Category 302/623 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 400095505 | verifiedrevid = 461113196
⚫ | IUPAC_name = {-3-({carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid
| image = Fosamprenavir.svg | image = Fosamprenavir structure.svg
| alt =
| image2 = Fosamprenavir ball-and-stick.png
| alt2 =
| USAN = Fosamprenavir calcium


<!--Clinical data--> <!--Clinical data-->
| tradename = Lexiva | tradename = Lexiva, Telzir
| Drugs.com = {{drugs.com|monograph|lexiva}} | Drugs.com = {{drugs.com|monograph|fosamprenavir}}
| MedlinePlus = a604012 | MedlinePlus = a604012
| pregnancy_AU = B3
| pregnancy_category = C <small>(United States)</small>
| licence_EU = yes
| legal_status = ] <small>(U.S.)</small>, POM <small>(UK)</small>
| routes_of_administration = Oral | routes_of_administration = ]
⚫ | 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>


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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<!--Identifiers--> <!--Identifiers-->
| index2_label = as salt
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = <!-- blanked - oldvalue: 226700-81-8 --> | CAS_number = 226700-79-4
⚫ | ATC_prefix = J05
| CAS_number2_Ref = {{cascite|correct|CAS}}
⚫ | ATC_suffix = AE07
| CAS_number2 = 226700-81-8
| PubChem = 131536 | PubChem = 131536
| PubChem2 = 131535
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01319 | DrugBank = DB01319
| DrugBank2 = DBSALT001228
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 116245 | ChemSpiderID = 116245
| ChemSpiderID2 = 116244
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = WOU1621EEG | UNII = WOU1621EEG
| ChEMBL_Ref = {{ebicite|changed|EBI}} | UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = ID1GU2627N
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D02497
| KEGG2 = D03835
| ChEBI = 82941
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1664 | ChEMBL = 1664
| ChEMBL2 = 1200734
| NIAID_ChemDB = 082186


<!--Chemical data--> <!--Chemical data-->
⚫ | IUPAC_name = {-3-({carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid
| C=25 | H=36 | N=3 | O=9 | P=1 | S=1 | C=25 | H=36 | N=3 | O=9 | P=1 | S=1
| molecular_weight = 585.608 ]/]<br>623.700 g/mol (] salt)
| smiles = O=C(O1CCOC1)N(Cc2ccccc2)(OP(=O)(O)O)CN(CC(C)C)S(=O)(=O)c3ccc(N)cc3 | SMILES = O=C(O1CCOC1)N(Cc2ccccc2)(OP(=O)(O)O)CN(CC(C)C)S(=O)(=O)c3ccc(N)cc3
⚫ | InChI = 1/C25H36N3O9PS/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)/t21-,23-,24+/m0/s1
| InChIKey = MLBVMOWEQCZNCC-OEMFJLHTBM
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C25H36N3O9PS/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)/t21-,23-,24+/m0/s1 | StdInChI = 1S/C25H36N3O9PS/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)/t21-,23-,24+/m0/s1
⚫ | 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MLBVMOWEQCZNCC-OEMFJLHTSA-N | StdInChIKey = MLBVMOWEQCZNCC-OEMFJLHTSA-N
| StdInChIKey2 = PMDQGYMGQKTCSX-HQROKSDRSA-L
}} }}

'''Fosamprenavir''' ('''FPV'''), sold under the brand names '''Lexiva''' and '''Telzir''', is a ] used to treat ].<ref name="Lexiva FDA label" /><ref name="Telzir EPAR" /> It is a ] of the ] and ] ].<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 ] as the ] 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. ] (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 ] 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 ] infections, typically but not necessarily in combination with low-dose ] 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 = ] | title = Lexiva | id = {{drugs.com|monograph|lexiva}}}}</ref>

==Adverse effects==
The most common adverse effect is diarrhea. Other common side effects include ], dizziness and exanthema, which is usually transient. Severe allergic reactions (]) 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 ] 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 ].<ref name="Austria-Codex" />

] 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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