DT-Web

DB00478 - Rimantadine


Identification
Name Rimantadine
Accession Number DB00478 (APRD01219)
Type small molecule
Description An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza. [PubChem]
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 179.3018
Groups approved
Monoisotopic Weight 179.167399677
Pharmacology
Indication For the prophylaxis and treatment of illness caused by various strains of influenza A virus in adults.
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.
Absorption Well absorbed, with the tablet and syrup formulations being equally absorbed after oral administration.
Protein binding Approximately 40% over typical plasma concentrations.
Biotransformation 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.
Toxicity 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.
Affected organisms
  • Human Influenza A Virus
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Matrix protein 2
Name Matrix protein 2
Gene Name M
Pharmacological action yes
Actions other/unknown
References
  • 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
  • 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. Epub 2008 Jul 31. - Pubmed
  • 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
  • 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. - Pubmed
  • 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. Epub 2008 Jun 8. - Pubmed
DTHybrid score 1.0758

Predictions


Id Partner name Gene Name Score
3876 Aromatic-L-amino-acid decarboxylase DDC 0.0518
706 Glutamate [NMDA] receptor subunit 3A GRIN3A 0.0453
3939 Amine oxidase [flavin-containing] B MAOB 0.0361
6144 Solute carrier family 22 member 2 SLC22A2 0.0341
6145 Solute carrier family 22 member 1 SLC22A1 0.0325
831 D(2) dopamine receptor DRD2 0.0324
1588 Multidrug resistance protein 1 ABCB1 0.0244
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