|Accession Number||DB00478 (APRD01219)|
An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza. [PubChem]
|External IDs||Not Available|
|Approved Prescription Products|
|Approved Generic Prescription Products|
|Approved Over the Counter Products||Not Available|
|Unapproved/Other Products||Not Available|
|International Brands||Not Available|
|Weight||Average: 179.3018 |
For the prophylaxis and treatment of illness caused by various strains of influenza A virus in adults.
Rimantadine, a cyclic amine, is a synthetic antiviral drug and a derivate of adamantane, like a similar drug amantadine. Rimantadine is inhibitory to the in vitro replication of influenza A virus isolates from each of the three antigenic subtypes (H1N1, H2H2 and H3N2) that have been isolated from man. Rimantadine has little or no activity against influenza B virus. Rimantadine does not appear to interfere with the immunogenicity of inactivated influenza A vaccine.
|Mechanism of action|
The mechanism of action of rimantadine is not fully understood. Rimantadine appears to exert its inhibitory effect early in the viral replicative cycle, possibly inhibiting the uncoating of the virus. Genetic studies suggest that a virus protein specified by the virion M2 gene plays an important role in the susceptibility of influenza A virus to inhibition by rimantadine.
Well absorbed, with the tablet and syrup formulations being equally absorbed after oral administration.
|Volume of distribution||Not Available|
Approximately 40% over typical plasma concentrations.
Following oral administration, rimantadine is extensively metabolized in the liver with less than 25% of the dose excreted in the urine as unchanged drug. Glucuronidation and hydroxylation are the major metabolic pathways.
|Route of elimination|
Following oral administration, rimantadine is extensively metabolized in the liver with less than 25% of the dose excreted in the urine as unchanged drug.
25 to 30 hours in young adults (22 to 44 years old). Approximately 32 hours in elderly (71 to 79 years old) and in patients with chronic liver disease. Approximately 13 to 38 hours in children (4 to 8 years old).
Oral LD50 in rats is 640 mg/kg. Overdoses of a related rug, amantadine, have been reported with adverse reactions consisting of agitation, hallucinations, cardiac arrhythmia and death.
|Pharmacogenomic Effects/ADRs||Not Available|
|Drug Interactions||Not Available|
|Food Interactions||Not Available|
|General References||Not Available|
|ATC Codes||J05AC02 — Rimantadine|
|AHFS Codes||Not Available|
|PDB Entries||Not Available|
|FDA label||Download (62.4 KB)|
|MSDS||Download (62.7 KB)|
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
|Predicted ADMET features|
|Mass Spec (NIST)||Not Available|
|Description||This compound belongs to the class of chemical entities known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.|
|Super Class||Organic compounds|
|Class||Organic nitrogen compounds|
|Sub Class||Organonitrogen compounds|
|Alternative Parents||Organopnictogen compounds / Hydrocarbon derivatives|
|Substituents||Organopnictogen compound / Hydrocarbon derivative / Primary aliphatic amine / Aliphatic homopolycyclic compound|
|Molecular Framework||Aliphatic homopolycyclic compounds|
|External Descriptors||Not Available|
- Influenza A virus (strain A/Ann Arbor/6/1960 H2N2)
- Pharmacological action
- General Function:
- Ion channel activity
- Specific Function:
- Forms a proton-selective ion channel that is necessary for the efficient release of the viral genome during virus entry. After attaching to the cell surface, the virion enters the cell by endocytosis. Acidification of the endosome triggers M2 ion channel activity. The influx of protons into virion interior is believed to disrupt interactions between the viral ribonucleoprotein (RNP), matrix pro...
- Gene Name:
- Uniprot ID:
- Molecular Weight:
- 11165.62 Da
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
- Jing X, Ma C, Ohigashi Y, Oliveira FA, Jardetzky TS, Pinto LH, Lamb RA: Functional studies indicate amantadine binds to the pore of the influenza A virus M2 proton-selective ion channel. Proc Natl Acad Sci U S A. 2008 Aug 5;105(31):10967-72. doi: 10.1073/pnas.0804958105. Epub 2008 Jul 31. [PubMed:18669647 ]
- Melidou A, Kyriazopoulou V, Diza E, Alexiou S, Pierroutsakos Y: Antiviral resistance of influenza A (H3N2) strains isolated in northern Greece between 2004 and 2007. Euro Surveill. 2009 Jan 29;14(4). pii: 19104. [PubMed:19215710 ]
- Chuang GY, Kozakov D, Brenke R, Beglov D, Guarnieri F, Vajda S: Binding hot spots and amantadine orientation in the influenza a virus M2 proton channel. Biophys J. 2009 Nov 18;97(10):2846-53. doi: 10.1016/j.bpj.2009.09.004. [PubMed:19917240 ]
- Intharathep P, Laohpongspaisan C, Rungrotmongkol T, Loisruangsin A, Malaisree M, Decha P, Aruksakunwong O, Chuenpennit K, Kaiyawet N, Sompornpisut P, Pianwanit S, Hannongbua S: How amantadine and rimantadine inhibit proton transport in the M2 protein channel. J Mol Graph Model. 2008 Oct;27(3):342-8. doi: 10.1016/j.jmgm.2008.06.002. Epub 2008 Jun 8. [PubMed:18620883 ]