U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of RIMANTADINE

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

HIDE SMILES / InChI

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 ( + / - )

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
FLUMADINE

Approved Use

Rimantadine 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 Date

1993
Curative
FLUMADINE

Approved Use

Rimantadine 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 Date

1993
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
20300 ng × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
healthy, 32.1
n = 64
Health Status: healthy
Age Group: 32.1
Sex: M+F
Population Size: 64
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Antiviral agents. 2. Structure-activity relationships of compounds related to 1-adamantanamine.
1971 Jun
Influence of membrane (M) protein on influenza A virus virion transcriptase activity in vitro and its susceptibility to rimantadine.
1980 Feb
Combined interferon-alpha 2, rimantadine hydrochloride, and ribavirin inhibition of influenza virus replication in vitro.
1984 Jan
Rimantadine and seizures.
1989 Feb 15
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
A novel approach to antiviral therapy for influenza.
1999 Nov
What should we advise about adjunctive therapies, including herbal medicines, for hepatitis C?
2000 May
A rapid assay for evaluation of antiviral activity against coxsackie virus B3, influenza virus A, and herpes simplex virus type 1.
2001 Jun
Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.
2002 Oct
Heterocyclic rimantadine analogues with antiviral activity.
2003 Dec 1
Potentiation of azole antifungals by 2-adamantanamine.
2013 Aug
Patents

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:34:06 GMT 2023
Edited
by admin
on Fri Dec 15 16:34:06 GMT 2023
Record UNII
0T2EF4JQTU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIMANTADINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
rimantadine [INN]
Common Name English
RIMANTADINE [HSDB]
Common Name English
(RS)-1-(1-ADAMANTYL)ETHANAMINE
Systematic Name English
RIMANTADINE [MI]
Common Name English
RIMANTADINE [VANDF]
Common Name English
Rimantadine [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175543
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
NCI_THESAURUS C281
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
WHO-ATC J05AC02
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
WHO-VATC QJ05AC02
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
LIVERTOX NBK547927
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
NDF-RT N0000175542
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C61927
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID2023561
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PRIMARY
SMS_ID
100000080585
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY
FDA UNII
0T2EF4JQTU
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY
LACTMED
Rimantadine
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY
EVMPD
SUB10320MIG
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY
DRUG BANK
DB00478
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY
HSDB
7438
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PRIMARY
INN
2292
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PRIMARY
CAS
13392-28-4
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PRIMARY
RXCUI
9386
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PRIMARY RxNorm
DRUG CENTRAL
2383
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PRIMARY
DAILYMED
0T2EF4JQTU
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY
PUBCHEM
5071
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY
MERCK INDEX
m9621
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY Merck Index
MESH
D012299
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PRIMARY
ChEMBL
CHEMBL959
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY
WIKIPEDIA
RIMANTADINE
Created by admin on Fri Dec 15 16:34:06 GMT 2023 , Edited by admin on Fri Dec 15 16:34:06 GMT 2023
PRIMARY
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