rimantadine

Trade name: flumadine

Small moleculeapproved

Approved

Sep 17, 1993

Rimantadine (INN, sold under the trade name Flumadine) is an orally administered antiviral drug used to treat, and in rare cases prevent, influenzavirus A infection. Rimantadine is an M2 ion channel inhibitor which specifically inhibits the replication of influenza A viruses by interfering with the uncoating process of the virus. M2 inhibitors block the ion channel formed by the M2 protein that spans the viral membrane (Hay 1985, Sugrue 1991). The influenza virus enters its host cell by receptor-mediated endocytosis. Thereafter, acidification of the endocytotic vesicles is required for the dissociation of the M1 protein from the ribonucleoprotein complexes. Only then are the ribonucleoprotein particles imported into the nucleus via the nuclear pores. The hydrogen ions needed for acidification pass through the M2 channel. The drug is effective against all influenza A subtypes that have previously caused disease in humans (H1N1, H2N2, and H3N2), but not against influenza B virus because the M2 protein is unique to influenza A viruses. Rimantadine is not active against the avian flu subtype H5N1 strains that have recently caused disease in humans. — NCATS

Clinical trial activity

1 trials · 1 clinical orgs · 7 marketing orgs

Phase 1
1
Phase 2
0
Phase 3
0
Phase 4
0

Earliest trial started Aug 1, 2009 (NCT01172847)

Timeline

1990s

  1. Sep 17, 1993

    Roche — Earliest FDA Approval

  2. Sep 17, 1993

    Forest Laboratories — NDA Secondary Org

  3. Sep 17, 1993

    Sun Pharmaceuticals — NDA Secondary Org

  4. Sep 17, 1993

    Roche — NDA Organization

2000s

  1. Aug 30, 2002

    Impax Laboratories — Marketing Organization

  2. Jan 14, 2003

    Actavis — Marketing Organization

  3. Jan 14, 2003

    Heritage Pharma — Marketing Organization

  4. Jan 14, 2003

    Chartwell Pharmaceuticals — Marketing Organization

  5. Jan 1, 2009

    Roche — Earliest Phase 1 Sponsor(trial)

Indications

Mechanism of action

Approval history

  • approvedPriority reviewSep 17, 1993

Chemistry & pharmacology

Loading structure…

SMILES

CC(N)C12CC3CC(CC(C3)C1)C2
Mol. weight
179.31 g/mol
Lipinski Ro5
Pass
Rule of 3
Yes
Chirality
Racemic Mixture
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 1-rimantadine
  • algirem
  • exp-126
  • exp-126
  • flumadine
  • flumadine
  • flumadine
  • meradan
  • meradan
  • rimantadin
  • rimantadin
  • rimantadin
  • rimantadine
  • rimantadine
  • rimantadine
  • rimantadine
  • rimantadine
  • rimantadine
  • rimantadine
  • rimantadine
  • rimantadine
  • rimantadine
  • (+/-)-rimantadine
  • rimantadine hcl
  • rimantadine hcl
  • rimantadine hcl
  • rimantadine hydrochloride
  • rimantadine hydrochloride
  • rimantadine hydrochloride
  • rimantadine hydrochloride
  • roflual
  • roflual

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT01172847Phase 1Aug 1, 2009Roche
Showing 1 of 1 trials
Page 1 / 1

Organizations

Research & Development (1)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
RocheFor profit1112009
1 organizations
Page 1 / 1

Marketing (9)

OrganizationOrg typeRelationshipDate
ActavisFor profitMKTGJan 14, 2003
Chartwell PharmaceuticalsFor profitMKTGJan 14, 2003
Forest LaboratoriesFor profitNDA2Sep 17, 1993
Heritage PharmaFor profitSYNJan 14, 2003
Heritage PharmaFor profitMKTGJan 14, 2003
Impax LaboratoriesFor profitMKTGAug 30, 2002
Impax LaboratoriesFor profitSYNNov 2, 2001
RocheFor profitNDASep 17, 1993
Sun PharmaceuticalsFor profitNDA2Sep 17, 1993