| Stereochemistry | RACEMIC |
| Molecular Formula | C12H21N |
| Molecular Weight | 179.3018 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(N)C12CC3CC(CC(C3)C1)C2
InChI
InChIKey=UBCHPRBFMUDMNC-UHFFFAOYSA-N
InChI=1S/C12H21N/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12/h8-11H,2-7,13H2,1H3
| Molecular Formula | C12H21N |
| Molecular Weight | 179.3018 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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.
CNS Activity
Originator
Approval Year
Doses
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
Drug as victim
Sourcing
PubMed
Sample Use Guides
100 mg PO q12hr preferably within 48 hours after onset of signs and symptoms of influenza A infection
Route of Administration:
Oral
The rimantadine_resistant variant of influenza virus A/Aichi/68 was obtained as follows. Initially the ED50 value was 0.612 μg/mL, which ensured the inhibition of viral hemagglutinin formation and more than 50% prevention of the development of the virus induced cytopathic effect (CPE). This virus was passaged three times in MDCK cells in the presence of increasing concentrations of rimantadine hydrochloride. Its final concentration was 50 μg/mL. Reproduction of influenza virus in cells MDCK (infectious titer) is not inhibited by the drug at a concentration of 25–50 μg/mL. This virus was denoted by us as A/Aichi/68/Rr.Initially, influenza viruses A/H5N1 and A/H1N1pdm09 were also resistant to rimantadine. Their infectious titer was not inhibited by rimantadine at a concentration of 25 μg/mL.
