Fosamprenavir

Fosamprenavir
Clinical data
Trade namesLexiva, Telzir
Other namesFosamprenavir calcium (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa604012
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityUnknown
Protein binding90%
MetabolismHydrolysed to amprenavir and phosphate in GI tract epithelium
Elimination half-life7.7 hours
ExcretionFecal (as metabolites of amprenavir)
Identifiers
  • {[(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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H36N3O9PS
Molar mass585.61 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:MLBVMOWEQCZNCC-OEMFJLHTSA-N checkY

  • 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
 ☒NcheckY (what is this?)  (verify)

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]

  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.
  3. ^ 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.
  4. ^ a b c d "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 2021-06-28. Retrieved 2022-10-03.
  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.