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Showing drug card for Rimantadine (DB00478)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:33
Primary Accession Number DB00478
Secondary Accession Number
  • APRD01219
Name Rimantadine
Drug Type
  • Approved
  • Small Molecule
Description An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza. [PubChem]
Synonyms Not Available
Brand Names
  1. Flumadine
  2. Levofloxacin hydrochloride
  3. Rimantadine HCL
Brand Mixtures Not Available
Chemical IUPAC Name 1-(1-adamantyl)ethanamine
Chemical Formula C12H21N
Chemical Structure Structure
CAS Registry Number 13392-28-4
InChI Identifier InChI=1/C12H21N/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12/h8-11H,2-7,13H2,1H3
InChI Key UBCHPRBFMUDMNC-UHFFFAOYAV
KEGG Drug Not Available
KEGG Compound C07236 Link Image
PubChem Compound 5071 Link Image
PubChem Substance 9445 Link Image
ChEBI ID Not Available
PharmGKB ID PA451252 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link http://www.rxlist.com/cgi/generic/rimantadine.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Rimantadine Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 179.3018
Monoisotopic Molecular Weight 179.1674
State Solid
Melting Point >300oC
Experimental Water Solubility Hydrochloride salt freely soluble (50 mg/ml at 20°C) Source: PhysProp
Predicted Water Solubility 9.15e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.6 Source: PhysProp
Predicted LogP 3.28 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.29 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES C[C@@H](N)[C@]12C[C@H]3C[C@H](C[C@H](C3)C1)C2
Canonical SMILES CC(N)C12CC3CC(CC(C3)C1)C2
Drug Category
  • Antiviral Agents
  • Nucleic Acid Synthesis Inhibitors
ATC Codes
AHFS Codes Not Available
Indication For the prophylaxis and treatment of illness caused by various strains of influenza A virus in adults.
Pharmacology 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.
Absorption Well absorbed, with the tablet and syrup formulations being equally absorbed after oral administration.
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.
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.
Half Life 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).
Dosage Forms
Form Route
Syrup Oral
Tablet, film coated Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
  2. RxList Link Image
Organisms Affected
  • Human Influenza A Virus
Targets
  1. Matrix protein 2
Drug Target 1 [top]
Target 1 ID 694
Target 1 Name Matrix protein 2
Target 1 Synonyms
  1. Proton channel protein M2
Target 1 Gene Name M
Target 1 Protein Sequence >Matrix protein 2 
MSLLTEVETPIRNEWGCRCNDSSDPLVVAASIIGILHLILWILDHLFFKCIYRFFKHGLK
RGPSTEGVPESMREEYRKEQQSAVDADDSHFVSIELE
Target 1 Number of Residues 98
Target 1 Molecular Weight 11166
Target 1 Theoretical pI 4.87
Target 1 GO Classification Not Available
Target 1 General Function Not Available
Target 1 Specific Function Forms a highly low-pH gated proton-selective channel. When the environmental pH is lower than a threshold, the M2 channel is activated and selectively transports protons across the membrane from the extracellular side to the cytoplasmic side. Crucial for the uncoating process. When the virion is internalized into the endosome, the channel acidifies the virion's interior, promoting the dissociation of matrix protein 1 (M1) from the ribonucleoprotein (RNP) thus allowing the transport of the RNP from the virion into the cell's nucleus. Also plays a role in viral proteins secretory pathway. Elevates the intravesicular pH of normally acidic compartments, such as trans-Golgi network, preventing newly formed hemagglutinin from premature switching to the fusion-active conformation
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 23-43
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 324265 Link Image
Target 1 UniProtKB/Swiss-Prot ID P21430 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name M2_IAANN Link Image
Target 1 PDB ID 1NYJ Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Virion
  • apical cell membrane
  • single-pass type III membrane protein
  • virion membrane. Cell membrane
Target 1 Gene Sequence >294 bp 
ATGAGTCTTCTAACCGAGGTCGAAACGCCTATCAGAAACGAATGGGGGTGCAGATGCAAC
GATTCAAGTGACCCTCTTGTTGTTGCCGCGAGTATCATTGGGATCTTGCACTTGATATTG
TGGATTCTTGATCATCTTTTTTTCAAATGCATTTATCGCTTCTTTAAACACGGTCTGAAA
AGAGGGCCTTCTACGGAAGGAGTACCAGAGTCTATGAGGGAAGAATATCGAAAGGAACAG
CAGAGTGCTGTGGATGCTGACGATAGTCATTTTGTCAGCATAGAGCTGGAGTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Lear JD: Proton conduction through the M2 protein of the influenza A virus; a quantitative, mechanistic analysis of experimental data. FEBS Lett. 2003 Sep 18;552(1):17-22. [PubMed Link Image]
  2. Wu Y, Voth GA: Computational studies of proton transport through the M2 channel. FEBS Lett. 2003 Sep 18;552(1):23-7. [PubMed Link Image]
  3. Cox NJ, Kitame F, Kendal AP, Maassab HF, Naeve C: Identification of sequence changes in the cold-adapted, live attenuated influenza vaccine strain, A/Ann Arbor/6/60 (H2N2). Virology. 1988 Dec;167(2):554-67. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.