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amprenavir

Trade name: agenerase

Small moleculeapprovedFast Track FDA

Approved

Apr 15, 1999

Amprenavir is an inhibitor of HIV-1 protease. Amprenavir binds to the active site of HIV-1 protease and thereby prevents the processing of viral gag and gag-pol polyprotein precursors, resulting in the formation of immature non-infectious viral particles. Amprenavir-containing combination regimens have shown virological efficacy, and have generally been well tolerated, in patients with HIV infection (primarily treatment-naive or protease inhibitor-naive). Fosamprenavir (GW433908, Lexiva, Telzir) is an oral prodrug of amprenavir, with a reduced daily pill burden. The use of protease inhibitors has also been associated with dyslipidemia and an increased risk of cardiovascular disease. Amprenavir activates Pregnane X receptor to mediate dyslipidemia. — NCATS

Clinical trial activity

41 trials · 20 clinical orgs · 1 marketing orgs

Phase 1
5
Phase 2
21
Phase 3
6
Phase 4
2

Earliest trial started Nov 1, 1997 (NCT00001758)

Timeline

1990s

  1. Jan 1, 1997

    Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 1998

    Earliest Phase 1 Sponsor(trial)

  3. Jan 1, 1999

    Earliest Phase 3 Sponsor(trial)

  4. Apr 15, 1999

    GlaxoSmithKline — Earliest FDA Approval

  5. Apr 15, 1999

    GlaxoSmithKline — NDA Organization

  6. Apr 15, 1999

    GlaxoSmithKline — NDA Secondary Org

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedAcceleratedFast trackApr 15, 1999

Chemistry & pharmacology

Loading structure…

SMILES

CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)S(=O)(=O)C3=CC=C(N)C=C3
Mol. weight
505.627 g/mol
Lipinski Ro5
1 violation(s)
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Discontinued

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 141w94
  • 141w94
  • 141w94
  • 141 w94
  • 141 w94
  • (3s)-tetrahydro-3-furanyl ((1s,2r)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate
  • (3s)-tetrahydro-3-furanyl ((1s,2r)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate
  • agenerase
  • agenerase
  • agenerase
  • agenerase
  • agenerase
  • amprenavir
  • amprenavir
  • amprenavir
  • amprenavir
  • amprenavir
  • amprenavir
  • amprenavir
  • amprenavir
  • amprenavir
  • amprenavir
  • amprenavir
  • amprenavir
  • amprenavir
  • amprénavir
  • amprénavir
  • amprenavirum
  • amprenavirum
  • angenerase
  • glaxosmithkline brand of amprenavir
  • glaxo wellcome brand of amprenavir
  • kvx-478
  • kvx-478
  • samprenavir
  • tetrahydro-3-furyl n-(3-(4-amino-n-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxypropyl)carbamate
  • vertex vx478
  • vx 478
  • vx-478
  • vx-478
  • vx-478

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT00192660Phase 4Feb 1, 2003National Heart, Lung, and Blood Institute (NHLBI), The National Centre in HIV Epidemiology and Clinical Research, Sydney, University of New South Wales
NCT00056641Phase 2Jan 1, 2003Boehringer Ingelheim
NCT00046033Phase 2Sep 18, 2002National Institute of Allergy and Infectious Diseases (NIAID), University of Pittsburgh
NCT00039741Phase 2/Phase 3 (Phase 3)Aug 1, 2002Duke University, National Institute of Allergy and Infectious Diseases (NIAID), National Institutes of Health (NIH), PENTA Foundation, University of Washington
NCT00038519Phase 2/Phase 3 (Phase 3)Apr 1, 2001Abbott
NCT00038532Phase 2Apr 1, 2001Abbott
NCT00005762N/AMar 1, 2001National Institute of Allergy and Infectious Diseases (NIAID)
NCT00006617N/ADec 6, 2000Glaxo Wellcome, National Institute of Allergy and Infectious Diseases (NIAID)
NCT00006591N/ADec 1, 2000Gathe, Joseph, M.D.
NCT00006578N/ADec 1, 2000National Institute of Allergy and Infectious Diseases (NIAID)
NCT00196625Phase 2Nov 1, 2000French National Agency for Research on AIDS and Viral Hepatitis
NCT00006152Phase 2Aug 7, 2000National Institute of Allergy and Infectious Diseases (NIAID)
NCT00005017Phase 4Apr 3, 2000Glaxo Wellcome
NCT00001968Phase 1Jan 1, 2000National Institute of Allergy and Infectious Diseases (NIAID)
NCT00002205N/ANov 2, 1999Glaxo Wellcome
NCT00002202Phase 3Nov 2, 1999Glaxo Wellcome
NCT00000919N/ANov 2, 1999National Institute of Allergy and Infectious Diseases (NIAID)
NCT00002195Phase 3Nov 2, 1999Glaxo Wellcome
NCT00002193Phase 3Nov 2, 1999Glaxo Wellcome
NCT00001095Phase 2Nov 2, 1999National Institute of Allergy and Infectious Diseases (NIAID)
Showing 20 of 41 trials
Page 1 / 3

Organizations

Research & Development (20)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Glaxo WellcomeFor profit181651999
National Institute of Allergy and Infectious Diseases (NIAID)Government161641997
AbbottFor profit2222001
Boehringer IngelheimFor profit2221999
Department of Veteran AffairsGovernment1011999
Duke UniversityAcademic/Hospital1012002
DuPontFor profit1011999
French National Agency for Research on AIDS and Viral HepatitisGovernment1112000
Gathe, Joseph, M.D.Academic/Hospital1112000
Gilead SciencesFor profit1111999
National Heart, Lung, and Blood Institute (NHLBI)Government1012003
National Institutes of Health (NIH)Government1012002
PENTA FoundationAcademic/Hospital1012002
RocheFor profit1111999
The National Centre in HIV Epidemiology and Clinical Research, SydneyAcademic/Hospital1012003
TrimerisFor profit1011999
University of ColoradoAcademic/Hospital1011999
University of New South WalesAcademic/Hospital1112003
University of PittsburghAcademic/Hospital1012002
University of WashingtonAcademic/Hospital1012002
20 organizations
Page 1 / 1

Marketing (2)

OrganizationOrg typeRelationshipDate
GlaxoSmithKlineFor profitNDAApr 15, 1999
GlaxoSmithKlineFor profitNDA2Apr 15, 1999