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GSK plc brands
Fosamprenavir
Другие языки:

Fosamprenavir

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Fosamprenavir
Fosamprenavir structure.svg
Fosamprenavir ball-and-stick.png
Clinical data
Trade names Lexiva, Telzir
Other names Fosamprenavir calcium (USAN US)
AHFS/Drugs.com Monograph
MedlinePlus a604012
License data
Pregnancy
category
  • AU: B3
Routes of
administration		 By mouth
ATC code
Legal status
Legal status
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
  • {[(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
Formula C25H36N3O9PS
Molar mass 585.61 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, 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.

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.

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.

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.

When combining fosamprenavir with low doses of the CYP3A4 inhibitor ritonavir, this interaction is intended as it allows for application of lower fosamprenavir doses.

Pharmacology

Fosamprenavir is quickly activated to amprenavir, even before it reaches the circulation. Amprenavir is a HIV protease inhibitor.

HIV-1 protease dimer with amprenavir (sticks) bound in the active site. PDB entry 3nu3

External links


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