rimantadine
Trade name: flumadine
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
Earliest trial started Aug 1, 2009 (NCT01172847)
Timeline
1990s
- Sep 17, 1993
Roche — Earliest FDA Approval
- Sep 17, 1993
Forest Laboratories — NDA Secondary Org
- Sep 17, 1993
Sun Pharmaceuticals — NDA Secondary Org
- Sep 17, 1993
Roche — NDA Organization
2000s
- Aug 30, 2002
Impax Laboratories — Marketing Organization
- Jan 14, 2003
Actavis — Marketing Organization
- Jan 14, 2003
Heritage Pharma — Marketing Organization
- Jan 14, 2003
Chartwell Pharmaceuticals — Marketing Organization
- Jan 1, 2009
Indications
Mechanism of action
- Influenza virus A matrix protein M2INHIBITOR
M2 inhibitor
Approval history
- approvedPriority reviewSep 17, 1993
Chemistry & pharmacology
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
- ChEMBLCHEMBL959 ↗
- WikipediaRimantadine ↗
- NCATS0T2EF4JQTU ↗
- ChEMBLCHEMBL535396 ↗
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 ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT01172847 | Phase 1 | Aug 1, 2009 | Roche |
Organizations
Research & Development (1)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Roche | For profit | 1 | 1 | 1 | 2009 |
Marketing (9)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Actavis | For profit | MKTG | Jan 14, 2003 |
| Chartwell Pharmaceuticals | For profit | MKTG | Jan 14, 2003 |
| Forest Laboratories | For profit | NDA2 | Sep 17, 1993 |
| Heritage Pharma | For profit | SYN | Jan 14, 2003 |
| Heritage Pharma | For profit | MKTG | Jan 14, 2003 |
| Impax Laboratories | For profit | MKTG | Aug 30, 2002 |
| Impax Laboratories | For profit | SYN | Nov 2, 2001 |
| Roche | For profit | NDA | Sep 17, 1993 |
| Sun Pharmaceuticals | For profit | NDA2 | Sep 17, 1993 |