Amprenavir

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Amprenavir
Amprenavir skeletal.svg
Systematic (IUPAC) name
(3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-1-phenylbutan-2-yl]carbamate
Clinical data
Trade names Agenerase
AHFS/Drugs.com monograph
MedlinePlus a699051
Licence data EMA:Link, US FDA:link
Pregnancy cat. C (US)
Legal status ?
Routes oral
Pharmacokinetic data
Protein binding 90%
Metabolism hepatic
Half-life 7.1-10.6 hours
Excretion <3% renal
Identifiers
CAS number 161814-49-9 YesY
ATC code J05AE05
PubChem CID 65016
DrugBank DB00701
ChemSpider 58532 YesY
UNII 5S0W860XNR YesY
KEGG D00894 YesY
ChEBI CHEBI:40050 YesY
ChEMBL CHEMBL116 YesY
NIAID ChemDB 006080
Chemical data
Formula C25H35N3O6S 
Mol. mass 505.628 g/mol
 YesY (what is this?)  (verify)

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.

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

HIV-1 Protease dimer with Amprenavir (sticks) bound in the active site. PDB entry 3nu3 [1]

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  1. ^ Shen, C. H.; Wang, Y. F.; Kovalevsky, A. Y.; Harrison, R. W.; Weber, I. T. (2010). "Amprenavir complexes with HIV-1 protease and its drug-resistant mutants altering hydrophobic clusters". FEBS Journal 277 (18): 3699–3714. doi:10.1111/j.1742-4658.2010.07771.x. PMC 2975871. PMID 20695887.  edit