Amprenavir

Amprenavir
Clinical data
Trade names	Agenerase
AHFS/Drugs.com	Monograph
MedlinePlus	a699051
License data	EU EMA: by INN; US FDA: Amprenavir;
Routes of; administration	Oral (capsules)
ATC code	J05AE05 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	90%
Metabolism	Hepatic
Elimination half-life	7.1–10.6 hours
Excretion	<3% renal
Identifiers
	IUPAC name (3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-1-phenylbutan-2-yl]carbamate;
CAS Number	161814-49-9 ;
PubChem CID	65016;
DrugBank	DB00701 ;
ChemSpider	58532 ;
UNII	5S0W860XNR;
KEGG	D00894 ;
ChEBI	CHEBI:40050 ;
ChEMBL	ChEMBL116 ;
NIAID ChemDB	006080;
CompTox Dashboard (EPA)	DTXSID5046061 ;
ECHA InfoCard	100.262.589
Chemical and physical data
Formula	C25H35N3O6S
Molar mass	505.63 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O[C@H]1CCOC1)N[C@@H](Cc2ccccc2)[C@H](O)CN(CC(C)C)S(=O)(=O)c3ccc(N)cc3;
	InChI 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 ; Key:YMARZQAQMVYCKC-OEMFJLHTSA-N ;
	(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.

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