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zanamivir

Trade name: relenza

Small moleculeapproved

Approved

Jul 26, 1999

Zanamivir, an antiviral agent, is a neuraminidase inhibitor indicated for treatment of uncomplicated acute illness due to influenza A and B virus in adults and pediatric patients 7 years and older who have been symptomatic for no more than 2 days. Zanamivir has also been shown to significantly inhibit the human sialidases NEU3 and NEU2 in the micromolar range (Ki 3.7 +/-0.48 and 12.9+/-0.07 uM, respectively), which could account for some of the rare side effects of zanamivir. The proposed mechanism of action of zanamivir is via inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release. By binding and inhibiting the neuraminidase protein, the drug renders the influenza virus unable to escape its host cell and infect others. Zanamivir was the first neuraminidase inhibitor commercially developed. It is currently marketed by GlaxoSmithKline under the trade name Relenza as a powder for oral inhalation. — NCATS

Clinical trial activity

20 trials · 22 clinical orgs · 2 marketing orgs

Phase 1
8
Phase 2
12
Phase 3
6
Phase 4
1

Earliest trial started Oct 1, 2007 (NCT00540501)

Timeline

1990s

  1. Jul 26, 1999

    Glaxo Wellcome — Earliest FDA Approval

  2. Jul 26, 1999

    Glaxo Wellcome — NDA Organization

  3. Jul 26, 1999

    GlaxoSmithKline — NDA Secondary Org

2000s

  1. Jan 1, 2007

    GlaxoSmithKline — Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 2008

    Earliest Phase 3 Sponsor(trial)

  3. Jan 1, 2009

    Earliest Phase 2 Sponsor(trial)

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedPriority reviewJul 26, 1999

Chemistry & pharmacology

Loading structure…

SMILES

CC(=O)N[C@@H]1[C@@H](NC(N)=N)C=C(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O
Mol. weight
332.3098 g/mol
Lipinski Ro5
1 violation(s)
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Topical
Availability
Prescription Only

Oral

No

Parenteral

No

Topical

Yes

Sources

Also known as

  • (2r,3r,4s)-3-(acetylamino)-4-carbamimidamido-2-[(1r,2r)-1,2,3-trihydroxypropyl]-3,4-dihydro-2h-pyran-6-carboxylic acid
  • (2r,3r,4s)-3-(acetylamino)-4-carbamimidamido-2-[(1r,2r)-1,2,3-trihydroxypropyl]-3,4-dihydro-2h-pyran-6-carboxylic acid
  • 4-guanidino-2,4-dideoxy-2,3-dehydro-n-acetylneuraminic acid
  • 4-guanidino-2,4-dideoxy-2,3-dehydro-n-acetylneuraminic acid
  • 4-guanidino-neu5ac2en
  • 4-guanidino-neu5ac2en
  • 5-acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-d-glycero-d-galacto-non-2-enonic acid
  • 5-acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-d-glycero-d-galacto-non-2-enonic acid
  • 5-(acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-d-glycero-d-galacto-non-2-enonic acid
  • 5-(acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-d-glycero-d-galacto-non-2-enonic acid
  • gana
  • gana
  • gg167
  • gg167
  • gna
  • gna
  • gr-121167
  • gr-121167
  • gr-121167x
  • gr-121167x
  • modified sialic acid
  • modified sialic acid
  • relenza
  • relenza
  • relenza
  • relenza
  • relenza
  • zanamavir
  • zanamavir
  • zanamavir
  • zanamivir
  • zanamivir
  • zanamivir
  • zanamivir
  • zanamivir
  • zanamivir
  • zanamivir
  • zanamivir
  • zanamivir
  • zanamivir
  • zanamivir
  • zanamivir hydrate
  • zanamivir hydrate
  • zmr
  • zmr

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT05648448Phase 2Dec 22, 2022University of Oxford
NCT04597437Early Phase 1 (Phase 1)Oct 1, 2021Allied Research International, George Washington University, Hospital Infantil de Niño Jesús de Barranquilla (HINJ), United States Navy, Universidad El Bosque, Bogotá
NCT04867707Phase 2Jul 14, 2021University of Missouri
NCT04494412Phase 2Dec 15, 2020GlaxoSmithKline
NCT02377401Phase 1Apr 28, 2015GlaxoSmithKline
NCT01527110Phase 3Jan 1, 2012GlaxoSmithKline
NCT01459081Phase 3Oct 1, 2011Second Military Medical University, Simcere Pharmaceutical Co., Ltd
NCT01353729Phase 1May 1, 2011GlaxoSmithKline
NCT01428479Phase 1Jan 7, 2011GlaxoSmithKline
NCT01231620Phase 3Jan 1, 2011GlaxoSmithKline
NCT01014988Phase 2Nov 1, 2009GlaxoSmithKline
NCT00989404Phase 1Oct 12, 2009GlaxoSmithKline
NCT00979667Phase 3Oct 1, 2009Chinese University of Hong Kong, City University of Hong Kong, Hong Kong Government
NCT00980109Phase 4Sep 1, 2009National Institute of Allergy and Infectious Diseases (NIAID), University of Oxford
NCT00921726Phase 1Jul 1, 2009Johns Hopkins University, Mahidol University, National Institute of Allergy and Infectious Diseases (NIAID)
NCT00867139Phase 1/Phase 2 (Phase 2)Mar 1, 2009University of Washington
NCT00830323Phase 2Jan 1, 2009University of Lyon
NCT00799760Phase 3Dec 1, 2008GlaxoSmithKline, Roche, University of Paris
NCT00784784Phase 3Nov 1, 2008GlaxoSmithKline, Icahn School of Medicine at Mount Sinai, University of Toronto
NCT00540501Phase 1Oct 1, 2007GlaxoSmithKline
Showing 20 of 20 trials
Page 1 / 1

Organizations

Research & Development (22)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
GlaxoSmithKlineFor profit11932007
National Institute of Allergy and Infectious Diseases (NIAID)Government2122009
University of OxfordAcademic/Hospital2222009
Allied Research InternationalFor profit1012021
Chinese University of Hong KongAcademic/Hospital1112009
City University of Hong KongAcademic/Hospital1012009
George Washington UniversityAcademic/Hospital1112021
Hong Kong GovernmentGovernment1012009
Hospital Infantil de Niño Jesús de Barranquilla (HINJ)Academic/Hospital1012021
Icahn School of Medicine at Mount SinaiAcademic/Hospital1012008
Johns Hopkins UniversityAcademic/Hospital1012009
Mahidol UniversityAcademic/Hospital1012009
RocheFor profit1012008
Second Military Medical UniversityGovernment1012011
Simcere Pharmaceutical Co., LtdFor profit1112011
United States NavyGovernment1012021
Universidad El Bosque, BogotáAcademic/Hospital1012021
University of LyonAcademic/Hospital1112009
University of MissouriAcademic/Hospital1112021
University of ParisAcademic/Hospital1112008
22 organizations
Page 1 / 2

Marketing (2)

OrganizationOrg typeRelationshipDate
Glaxo WellcomeFor profitNDAJul 26, 1999
GlaxoSmithKlineFor profitNDA2Jul 26, 1999