Structure via PubChem · Public domain (PubChem)
آمپرناویر
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