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 eight very large 150 mg gel capsules or 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.