Amprenavir

Title: Amprenavir
CAS Registry Number: 161814-49-9
CAS Name: [(1S,2R)-3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid (3S)-tetrahydro-3-furanyl ester
Additional Names: 4-amino-N-((2syn,3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzene sulfonamide
Manufacturers' Codes: 141W94; KVX-478; VX-478
Trademarks: Agenerase (GSK); Prozei (Kissei)
Molecular Formula: C25H35N3O6S
Molecular Weight: 505.63
Percent Composition: C 59.38%, H 6.98%, N 8.31%, O 18.99%, S 6.34%
Literature References: Second generation HIV protease inhibitor. Prepn: R. D. Tung et al., WO 9405639; eidem, US 5585397 (1994, 1996 both to Vertex). Crystal structure of complex with HIV protease: E. E. Kim et al., J. Am. Chem. Soc. 117, 1181 (1995). Review of design strategy: M. A. Navia et al., Int. Antiviral News 3, 143-145 (1995); of pharmacology and clinical evaluation: J. C. Adkins, D. Faulds, Drugs 55, 837-842 (1998).
Properties: White to cream-colored solid. Soly in water (25°): 0.04 mg/ml.
Therap-Cat: Antiviral.
Keywords: HIV Protease Inhibitor; Antiviral; Peptidomimetics.
Amprolium Amprotropine Phosphate Ampyrone Amrubicin Amsacrine

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]