Amprenavir

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Amprenavir (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 eight very large gel capsules.

Amprenavir
Clinical data
Trade namesAgenerase
AHFS/Drugs.comMonograph
MedlinePlusa699051
License data
Routes of
administration
oral
ATC code
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 mass505.628 g/mol 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
 ☒NcheckY (what is this?)  (verify)

Production of amprenavir was discontinued by the manufacturer December 31, 2004; a prodrug version (fosamprenavir) is available.

See also