Structure via PubChem · Public domain (PubChem)
amprenavir
Sign in to saveAlso known as VX-478, 141 W94, KVX-478, (3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate
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.
Chemical data
- Formula
- C25H35N3O6S
- Molecular weight
- 505.6 g/mol
- IUPAC name
- [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
- SMILES
- CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
- InChIKey
- YMARZQAQMVYCKC-OEMFJLHTSA-N
- XLogP
- 2.9
- Polar surface area
- 140 Ų
- H-bond donors
- 3
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1999
- Admin. routes
- oral
- Indications
- HIV infection, AIDS, viral disease
via ChEMBL · EBI
Research
900 papers- Amprenavir.Drugs · 1998
- Amprenavir: a review of its clinical potential in patients with HIV infection.Drugs · 2000
- Amprenavir: a new human immunodeficiency virus type 1 protease inhibitor.Clinical therapeutics · 2000
- From amprenavir to GW433908.Journal of HIV therapy · 2001
- Amprenavir or fosamprenavir plus ritonavir in HIV infection: pharmacology, efficacy and tolerability profile.Drugs · 2005
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 505.225
- Has use
- medication
Show 9 more facts
- subject has role
- protease inhibitor
- chemical formula
- C₂₅H₃₅N₃O₆S
- significant drug interaction
- rifapentine
- medical condition treated
- HIV/AIDS
- World Health Organisation international non-proprietary name
- amprenavir
- canonical SMILES
- CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
- isomeric SMILES
- CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
- defined daily dose
- 1.2
- Commons category
- Amprenavir
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Background
- References
- External links
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.
Excerpted from Wikipedia’s “amprenavir” article, available under the CC BY-SA 4.0 licence.