Fosamprenavir

Fosamprenavir
Clinical data
Trade names	Lexiva, Telzir
Other names	Fosamprenavir calcium (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a604012
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	J05AE07 (WHO) ;
Legal status
Legal status	CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	Unknown
Protein binding	90%
Metabolism	Hydrolysed to amprenavir and phosphate in GI tract epithelium
Elimination half-life	7.7 hours
Excretion	Fecal (as metabolites of amprenavir)
Identifiers
	IUPAC name {[(2R,3S)-1-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid;
CAS Number	226700-79-4 ; as salt: 226700-81-8 ;
PubChem CID	131536; as salt: 131535;
DrugBank	DB01319 ; as salt: DBSALT001228;
ChemSpider	116245 ; as salt: 116244;
UNII	WOU1621EEG; as salt: ID1GU2627N ;
KEGG	D02497 ; as salt: D03835;
ChEBI	CHEBI:82941;
ChEMBL	ChEMBL1664 ; as salt: ChEMBL1200734;
NIAID ChemDB	082186;
CompTox Dashboard (EPA)	DTXSID2048296 ;
Chemical and physical data
Formula	C25H36N3O9PS
Molar mass	585.61 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI InChI=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 ; Key:MLBVMOWEQCZNCC-OEMFJLHTSA-N ; ; as salt: InChI=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; Key:PMDQGYMGQKTCSX-HQROKSDRSA-L;
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Fosamprenavir (FPV), sold under the brand names Lexiva and Telzir, is a medication used to treat HIV/AIDS.^[3]^[4] It is a prodrug of the protease inhibitor and antiretroviral drug amprenavir.^[5] It is marketed by ViiV Healthcare as the calcium salt.^[3]^[4]

Fosamprenavir was approved for medical use in the United States in October 2003,^[6] and in the European Union in July 2004.^[4] The human body metabolizes fosamprenavir in order to form amprenavir, which is the active ingredient.^[3]

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.^[7]

^ "Telzir Product information". Health Canada. 25 April 2012. Archived from the original on 14 June 2021. Retrieved 2 October 2022.
^ "Telzir 700 mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 22 June 2021. Archived from the original on 6 December 2021. Retrieved 2 October 2022.
^ ^a ^b ^c ^d "Lexiva- fosamprenavir calcium tablet, film coated Lexiva- fosamprenavir calcium suspension". DailyMed. 1 October 2020. Archived from the original on 29 January 2022. Retrieved 2 October 2022.
^ ^a ^b ^c ^d "Telzir EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 15 May 2021. Retrieved 2 October 2022.
^ "Fosamprenavir Monograph for Professionals". Archived from the original on 28 June 2021. Retrieved 3 October 2022.
^ "Drug Approval Package: Lexiva (Fosamprenavir Calcium) NDA #021548". U.S. Food and Drug Administration (FDA). Archived from the original on 15 April 2021. Retrieved 2 October 2022.
^ Eron J, Yeni P, Gathe J, Estrada V, DeJesus E, Staszewski S, et al. (August 2006). "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". Lancet. 368 (9534): 476–82. doi:10.1016/S0140-6736(06)69155-1. PMID 16890834. S2CID 33612672.{{cite journal}}: CS1 maint: overridden setting (link)

[1] "Telzir Product information". Health Canada. 25 April 2012. Archived from the original on 14 June 2021. Retrieved 2 October 2022.

[2] "Telzir 700 mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 22 June 2021. Archived from the original on 6 December 2021. Retrieved 2 October 2022.

[Lexiva_FDA_label-3] "Lexiva- fosamprenavir calcium tablet, film coated Lexiva- fosamprenavir calcium suspension". DailyMed. 1 October 2020. Archived from the original on 29 January 2022. Retrieved 2 October 2022.

[Telzir_EPAR-4] "Telzir EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 15 May 2021. Retrieved 2 October 2022.

[5] "Fosamprenavir Monograph for Professionals". Archived from the original on 28 June 2021. Retrieved 3 October 2022.

[6] "Drug Approval Package: Lexiva (Fosamprenavir Calcium) NDA #021548". U.S. Food and Drug Administration (FDA). Archived from the original on 15 April 2021. Retrieved 2 October 2022.

[7] Eron J, Yeni P, Gathe J, Estrada V, DeJesus E, Staszewski S, et al. (August 2006). "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". Lancet. 368 (9534): 476–82. doi:10.1016/S0140-6736(06)69155-1. PMID 16890834. S2CID 33612672.{{cite journal}}: CS1 maint: overridden setting (link)

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