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Identification
NameRimantadine
Accession NumberDB00478  (APRD01219)
TypeSmall Molecule
GroupsApproved
DescriptionAn RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza. [PubChem]
Structure
Thumb
Synonyms
Rimantadin
Rimantadine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FlumadineTablet100 mg/1OralCaraco Pharma, Inc.2009-09-22Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Rimantadine HydrochlorideTablet, film coated100 mg/1OralSTAT Rx USA LLC2005-04-01Not applicableUs
Rimantadine HydrochlorideTablet, film coated100 mg/1OralImpax Generics2005-04-01Not applicableUs
Rimantadine HydrochlorideTablet, film coated100 mg/1OralH.J. Harkins Company, Inc.2005-04-01Not applicableUs
Rimantadine HydrochlorideTablet, film coated100 mg/1Oralbryant ranch prepack2005-04-01Not applicableUs
Rimantadine HydrochlorideTablet, film coated100 mg/1OralCarilion Materials Management2005-04-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
RimantalistPhysician Therapeutics Llc
Salts
Name/CASStructureProperties
Rimantadine Hydrochloride
1501-84-4
Thumb
  • InChI Key: OZBDFBJXRJWNAV-UHFFFAOYNA-N
  • Monoisotopic Mass: 215.144077416
  • Average Mass: 215.763
DBSALT000833
Categories
UNII0T2EF4JQTU
CAS number13392-28-4
WeightAverage: 179.3018
Monoisotopic: 179.167399677
Chemical FormulaC12H21N
InChI KeyUBCHPRBFMUDMNC-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-(adamantan-1-yl)ethan-1-amine
SMILES
CC(N)C12CC3CC(CC(C3)C1)C2
Pharmacology
IndicationFor the prophylaxis and treatment of illness caused by various strains of influenza A virus in adults.
Structured Indications
PharmacodynamicsRimantadine, 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 actionThe 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Matrix protein 2Proteinyes
other/unknown
Influenza A virus (strain A/Ann Arbor/6/1960 H2N2)P21430 details
Related Articles
AbsorptionWell absorbed, with the tablet and syrup formulations being equally absorbed after oral administration.
Volume of distributionNot Available
Protein bindingApproximately 40% over typical plasma concentrations.
Metabolism

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 eliminationFollowing oral administration, rimantadine is extensively metabolized in the liver with less than 25% of the dose excreted in the urine as unchanged drug.
Half life25 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).
ClearanceNot Available
ToxicityOral 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis Reference

DrugSyn.org

US3352912
General ReferencesNot Available
External Links
ATC CodesJ05AC02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (62.4 KB)
MSDSDownload (62.7 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9798
Caco-2 permeable+0.6348
P-glycoprotein substrateNon-substrate0.6811
P-glycoprotein inhibitor INon-inhibitor0.8751
P-glycoprotein inhibitor IINon-inhibitor0.919
Renal organic cation transporterNon-inhibitor0.7654
CYP450 2C9 substrateNon-substrate0.8329
CYP450 2D6 substrateNon-substrate0.7244
CYP450 3A4 substrateNon-substrate0.6785
CYP450 1A2 substrateNon-inhibitor0.9086
CYP450 2C9 inhibitorNon-inhibitor0.8923
CYP450 2D6 inhibitorNon-inhibitor0.7561
CYP450 2C19 inhibitorNon-inhibitor0.872
CYP450 3A4 inhibitorNon-inhibitor0.7651
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8323
Ames testNon AMES toxic0.7955
CarcinogenicityNon-carcinogens0.8471
BiodegradationNot ready biodegradable0.9782
Rat acute toxicity2.0121 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9845
hERG inhibition (predictor II)Non-inhibitor0.8704
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Forest laboratories inc
  • Caraco pharmaceutical laboratories ltd
  • Actavis totowa llc
  • Corepharma llc
  • Impax laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral100 mg/1
Tablet, film coatedOral100 mg/1
Kit
Prices
Unit descriptionCostUnit
Levofloxacin hemihydr 100% powder42.69USD g
Levaquin 750 mg leva-pak tablet27.51USD tablet
Levaquin 750 mg tablet27.51USD tablet
Iquix 1.5% eye drops15.71USD ml
Levaquin 500 mg tablet14.69USD tablet
Levaquin 250 mg tablet14.09USD tablet
Quixin 0.5% eye drops12.21USD ml
Rimantadine hcl 100 mg tablet2.44USD tablet
Flumadine 100 mg tablet2.4USD tablet
Levaquin i.v. 25 mg/ml vial1.94USD ml
Levaquin 500 mg/100 ml d5w0.44USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point>300 °CNot Available
water solubilityHydrochloride salt freely soluble (50 mg/ml at 20 °C)Not Available
logP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00915 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
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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

Targets

Kind
Protein
Organism
Influenza A virus (strain A/Ann Arbor/6/1960 H2N2)
Pharmacological action
yes
Actions
other/unknown
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:
M
Uniprot ID:
P21430
Molecular Weight:
11165.62 Da
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:17016423 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:11