Amprenavir

Amprenavir
Clinical data
Trade namesAgenerase
AHFS/Drugs.comMonograph
MedlinePlusa699051
License data
Routes of
administration		Oral (capsules)
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding90%
MetabolismHepatic
Elimination half-life7.1–10.6 hours
Excretion<3% renal
Identifiers
  • (3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-1-phenylbutan-2-yl]carbamate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.262.589 Edit this at Wikidata
Chemical and physical data
FormulaC25H35N3O6S
Molar mass505.63 g·mol−1
3D model (JSmol)
  • O=C(O[C@H]1CCOC1)N[C@@H](Cc2ccccc2)[C@H](O)CN(CC(C)C)S(=O)(=O)c3ccc(N)cc3
  • InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1 checkY
  • Key:YMARZQAQMVYCKC-OEMFJLHTSA-N checkY
  (verify)

Amprenavir (original brand name Agenerase, GlaxoSmithKline) is a protease inhibitor used to treat HIV infection. It was approved by the Food and Drug Administration on April 15, 1999, for twice-a-day dosing instead of needing to be taken every eight hours. The convenient dosing came at a price, as the dose required is 1,200 mg, delivered in 8 (eight) very large 150 mg gel capsules or 24 (twenty-four) 50 mg gel capsules twice daily.[1]

It was patented in 1992 and approved for medical use in 1999.[2] Production of amprenavir was discontinued by the manufacturer on December 31, 2004; a prodrug version (fosamprenavir), is available.

  1. ^ "Agenerase (amprenavir) Capsules. Full Prescribing Information. Section Dosage and Administration" (PDF). US Food and Drug Administration. GlaxoSmithKline and Vertex Pharmaceuticals Inc. Retrieved 29 November 2015.
  2. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 509. ISBN 9783527607495.