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. It is a prodrug of the protease inhibitor and antiretroviral drug amprenavir. It is marketed by ViiV Healthcare as the calcium salt.

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

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.