Amprenavir

Amprenavir

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 Y
ATC code	J05AE05
PubChem	CID 65016
DrugBank	DB00701
ChemSpider	58532 Y
UNII	5S0W860XNR Y
KEGG	D00894 Y
ChEBI	CHEBI:40050 Y
ChEMBL	CHEMBL116 Y
NIAID ChemDB	006080
Chemical data
Formula	C25H35N3O6S
Mol. mass	505.628 g/mol
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 Y Key:YMARZQAQMVYCKC-OEMFJLHTSA-N Y
Y (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

See also

• Fosamprenavir, a prodrug of amprenavir

External links

• Amprenavir bound to proteins in the PDB