Details
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 |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00478 | http://reference.medscape.com/drug/flumadine-rimantadine-342626 | https://www.drugs.com/drug-interactions/rimantadine.html | https://www.ncbi.nlm.nih.gov/pubmed/3346834
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00478 | http://reference.medscape.com/drug/flumadine-rimantadine-342626 | https://www.drugs.com/drug-interactions/rimantadine.html | https://www.ncbi.nlm.nih.gov/pubmed/3346834
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1772930 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25342196 |
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Target ID: CHEMBL1743122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23241029 |
4.4 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | FLUMADINE Approved UseRimantadine hydrochloride tablet is indicated for the prophylaxis and treatment of illness caused by various strains of influenza A virus in adults (17 years and older). Rimantadine hydrochloride tablet is indicated for prophylaxis against influenza A virus in children (1 year to 16 years of age). PROPHYLAXIS In controlled studies of children (1 year to 16 years of age), healthy adults (17 years and older), and elderly patients (65 years of age and older), rimantadine hydrochloride has been shown to be safe and effective in preventing signs and symptoms of infection caused by various strains of influenza A virus. Since rimantadine hydrochloride does not completely prevent the host immune response to influenza A infection, individuals who take this drug may still develop immune responses to natural disease or vaccination and may be protected when later exposed to antigenically-related viruses. Following vaccination during an influenza outbreak, rimantadine hydrochloride prophylaxis should be considered for the 2 to 4 week time period required to develop an antibody response. However, the safety and effectiveness of rimantadine hydrochloride prophylaxis have not been demonstrated for longer than 6 weeks. TREATMENT Rimantadine hydrochloride therapy should be considered for adults (17 years and older) who develop an influenza-like illness during known or suspected influenza A infection in the community. When administered within 48 hours after onset of signs and symptoms of infection caused by influenza A virus strains, rimantadine hydrochloride has been shown to reduce the duration of fever and systemic symptoms. The following points should be considered before initiating treatment or prophylaxis with rimantadine hydrochloride: Rimantadine hydrochloride is not a substitute for early vaccination on an annual basis as recommended by the Centers for Disease Control and Prevention Advisory Committee on Immunization Practices Influenza viruses change over time. Emergence of resistance mutations could decrease drug effectiveness. Other factors (for example, changes in viral virulence) might also diminish clinical benefit of antiviral drugs. Prescribers should consider available information on influenza drug susceptibility patterns and treatment effects when deciding whether to use rimantadine hydrochloride. Launch Date1993 |
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Curative | FLUMADINE Approved UseRimantadine hydrochloride tablet is indicated for the prophylaxis and treatment of illness caused by various strains of influenza A virus in adults (17 years and older). Rimantadine hydrochloride tablet is indicated for prophylaxis against influenza A virus in children (1 year to 16 years of age). PROPHYLAXIS In controlled studies of children (1 year to 16 years of age), healthy adults (17 years and older), and elderly patients (65 years of age and older), rimantadine hydrochloride has been shown to be safe and effective in preventing signs and symptoms of infection caused by various strains of influenza A virus. Since rimantadine hydrochloride does not completely prevent the host immune response to influenza A infection, individuals who take this drug may still develop immune responses to natural disease or vaccination and may be protected when later exposed to antigenically-related viruses. Following vaccination during an influenza outbreak, rimantadine hydrochloride prophylaxis should be considered for the 2 to 4 week time period required to develop an antibody response. However, the safety and effectiveness of rimantadine hydrochloride prophylaxis have not been demonstrated for longer than 6 weeks. TREATMENT Rimantadine hydrochloride therapy should be considered for adults (17 years and older) who develop an influenza-like illness during known or suspected influenza A infection in the community. When administered within 48 hours after onset of signs and symptoms of infection caused by influenza A virus strains, rimantadine hydrochloride has been shown to reduce the duration of fever and systemic symptoms. The following points should be considered before initiating treatment or prophylaxis with rimantadine hydrochloride: Rimantadine hydrochloride is not a substitute for early vaccination on an annual basis as recommended by the Centers for Disease Control and Prevention Advisory Committee on Immunization Practices Influenza viruses change over time. Emergence of resistance mutations could decrease drug effectiveness. Other factors (for example, changes in viral virulence) might also diminish clinical benefit of antiviral drugs. Prescribers should consider available information on influenza drug susceptibility patterns and treatment effects when deciding whether to use rimantadine hydrochloride. Launch Date1993 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
74 ng/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIMANTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
416 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3606083/ |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
RIMANTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
181 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3606083/ |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
RIMANTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20300 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3606083/ |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
RIMANTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8170 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3606083/ |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
RIMANTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25.4 h |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIMANTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
33 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3606083/ |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
RIMANTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
26 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3606083/ |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
RIMANTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
60% |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIMANTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Antiviral agents. 2. Structure-activity relationships of compounds related to 1-adamantanamine. | 1971 Jun |
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Influence of membrane (M) protein on influenza A virus virion transcriptase activity in vitro and its susceptibility to rimantadine. | 1980 Feb |
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Combined interferon-alpha 2, rimantadine hydrochloride, and ribavirin inhibition of influenza virus replication in vitro. | 1984 Jan |
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Rimantadine and seizures. | 1989 Feb 15 |
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4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid is a highly effective inhibitor both of the sialidase (neuraminidase) and of growth of a wide range of influenza A and B viruses in vitro. | 1993 Jul |
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A novel approach to antiviral therapy for influenza. | 1999 Nov |
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What should we advise about adjunctive therapies, including herbal medicines, for hepatitis C? | 2000 May |
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A rapid assay for evaluation of antiviral activity against coxsackie virus B3, influenza virus A, and herpes simplex virus type 1. | 2001 Jun |
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Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds. | 2002 Oct |
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Heterocyclic rimantadine analogues with antiviral activity. | 2003 Dec 1 |
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Potentiation of azole antifungals by 2-adamantanamine. | 2013 Aug |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24795106
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.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 16:34:06 GMT 2023
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on
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Record UNII |
0T2EF4JQTU
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175543
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NCI_THESAURUS |
C281
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WHO-ATC |
J05AC02
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WHO-VATC |
QJ05AC02
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LIVERTOX |
NBK547927
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NDF-RT |
N0000175542
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C61927
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100000080585
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0T2EF4JQTU
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Rimantadine
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SUB10320MIG
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DB00478
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7438
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9386
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2383
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0T2EF4JQTU
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m9621
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D012299
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CHEMBL959
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RIMANTADINE
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SALT/SOLVATE -> PARENT |
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TARGET ORGANISM->INHIBITOR |
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TARGET ORGANISM->INHIBITOR |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
PLASMA; URINE
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ACTIVE MOIETY |
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