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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:29:15 UTC
HMDB IDHMDB14621
Secondary Accession NumbersNone
Metabolite Identification
Common NameRimantadine
DescriptionRimantadine is only found in individuals that have used or taken this drug. It is an RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza. [PubChem]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.
Structure
Thumb
Synonyms
ValueSource
RimantadinChEMBL
Rimantadine hydrochlorideHMDB
Chemical FormulaC12H21N
Average Molecular Weight179.3018
Monoisotopic Molecular Weight179.167399677
IUPAC Name1-(adamantan-1-yl)ethan-1-amine
Traditional Namerimantadine
CAS Registry Number13392-28-4
SMILES
CC(N)C12CC3CC(CC(C3)C1)C2
InChI Identifier
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
InChI KeyInChIKey=UBCHPRBFMUDMNC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassPrimary amines
Direct ParentMonoalkylamines
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antiviral Agents
  • Nucleic Acid Synthesis Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.15e-03 g/LNot Available
LogP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0092 mg/mLALOGPS
logP3.28ALOGPS
logP2.22ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)10.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity54.52 m3·mol-1ChemAxon
Polarizability21.79 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00478
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00478
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00478
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4893
KEGG Compound IDC07236
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRimantadine
NuGOwiki LinkHMDB14621
Metagene LinkHMDB14621
METLIN IDNot Available
PubChem Compound5071
PDB IDNot Available
ChEBI ID193858
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available