Rimantadine

Identification

Summary

Rimantadine is an RNA synthesis inhibitor used to prevent influenza A infection.

Generic Name
Rimantadine
DrugBank Accession Number
DB00478
Background

An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 179.3018
Monoisotopic: 179.167399677
Chemical Formula
C12H21N
Synonyms
  • alpha-Methyl-1-adamantanemethylamine
  • alpha-Methyladamantanemethylamine
  • Rimantadina
  • Rimantadine
  • Rimantadinum

Pharmacology

Indication

For the prophylaxis and treatment of illness caused by various strains of influenza A virus in adults.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatInfluenza aCombination Product in combination with: Arginine (DB00125)•••••••••••••••••
Used in combination for prophylaxis ofInfluenza aCombination Product in combination with: Arginine (DB00125)••••••••••••
Prophylaxis ofInfluenza a••••••••••••
Treatment ofInfluenza a•••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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. The protein coded by the M2 gene of influenza A may play an important role in rimantadine susceptibility.

TargetActionsOrganism
AMatrix protein 2
other/unknown
Influenza A virus (strain A/Ann Arbor/6/1960 H2N2)
Absorption

Well absorbed, with the tablet and syrup formulations being equally absorbed after oral administration.

Volume of distribution

Not Available

Protein binding

Approximately 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 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.

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).

Clearance

Not Available

Adverse Effects
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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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Rimantadine.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Rimantadine.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Rimantadine.
Bacillus calmette-guerin substrain russian BCG-I live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Rimantadine.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Rimantadine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Rimantadine hydrochlorideJEI07OOS8Y1501-84-4OZBDFBJXRJWNAV-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FlumadineSyrup50 mg/5mLOralAllergan, Inc.1993-09-172008-01-31US flag
FlumadineTablet100 mg/1OralPhysicians Total Care, Inc.2009-09-222010-06-30US flag
FlumadineTablet100 mg/1OralAllergan, Inc.1993-09-172009-09-22US flag
FlumadineTablet100 mg/1OralSun Pharmaceutical Industries, Inc.2009-09-222017-08-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Rimantadine HydrochlorideTablet, film coated100 mg/1OralA-S Medication Solutions2005-04-012017-12-31US flag
Rimantadine HydrochlorideTablet, film coated100 mg/1OralCarilion Materials Management2005-04-01Not applicableUS flag
Rimantadine HydrochlorideTablet, film coated100 mg/1OralH.J. Harkins Company2005-04-01Not applicableUS flag
Rimantadine HydrochlorideTablet, film coated100 mg/1Oralbryant ranch prepack2005-04-01Not applicableUS flag
Rimantadine HydrochlorideTablet, film coated100 mg/1OralStat Rx USA2005-04-01Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
RimantalistRimantadine hydrochloride (100 mg/1) + Arginine (60 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag

Categories

ATC Codes
J05AC02 — Rimantadine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Monoalkylamines
Alternative Parents
Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Aliphatic homopolycyclic compound / Hydrocarbon derivative / Organopnictogen compound / Primary aliphatic amine
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Human Influenza A Virus

Chemical Identifiers

UNII
0T2EF4JQTU
CAS number
13392-28-4
InChI Key
UBCHPRBFMUDMNC-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

References

Synthesis Reference
US3352912
General References
Not Available
Human Metabolome Database
HMDB0014621
KEGG Drug
D08483
KEGG Compound
C07236
PubChem Compound
5071
PubChem Substance
46505973
ChemSpider
4893
BindingDB
50216627
RxNav
9386
ChEBI
94440
ChEMBL
CHEMBL959
Therapeutic Targets Database
DAP001087
PharmGKB
PA164748038
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Rimantadine
FDA label
Download (62.4 KB)
MSDS
Download (62.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers (HV)1
Not AvailableCompletedNot AvailableHepatitis C Virus (HCV) Infection1

Pharmacoeconomics

Manufacturers
  • Forest laboratories inc
  • Caraco pharmaceutical laboratories ltd
  • Actavis totowa llc
  • Corepharma llc
  • Impax laboratories inc
Packagers
  • Caraco Pharmaceutical Labs
  • Corepharma LLC
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Forest Pharmaceuticals
  • Global Pharmaceuticals
  • H.J. Harkins Co. Inc.
  • Impax Laboratories Inc.
  • Inwood Labs
  • McNeil Laboratories
  • Medisca Inc.
  • Nucare Pharmaceuticals Inc.
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prescript Pharmaceuticals
  • Sandoz
  • Southwood Pharmaceuticals
  • Vistakon Pharmaceuticals LLC
Dosage Forms
FormRouteStrength
SyrupOral50 mg/5mL
TabletOral100 mg/1
CapsuleOral100.000 mg
SolutionOral5.000 g
Tablet, film coatedOral100 mg/1
KitOral
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>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 RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9300000000-072e253cf8a14a11c5d8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01q9-0900000000-eba8c1b56d44c1b807c1
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03e9-0900000000-c08f5da97f667f13b1db
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1900000000-972fa1a7c772a975ad9a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-2900000000-c96720c327f1f9caf8ce
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-5900000000-ba6a44c981963072ddb1
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-06sl-9700000000-010211db22cfecb7a5c2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03e9-2900000000-3b569e326b02422cd07b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-4c5f0d7ce39b67866dca
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-b1c3a37a7a2509ef9966
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-7bed381f98e29c966fbb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-75c0770f1c5d0c6ff032
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-4661084061f92f70c251
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01p9-0900000000-7cd5c1a0208b02a75657
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-140.1059766
predicted
DarkChem Lite v0.1.0
[M-H]-143.84157
predicted
DeepCCS 1.0 (2019)
[M+H]+140.7453766
predicted
DarkChem Lite v0.1.0
[M+H]+146.19958
predicted
DeepCCS 1.0 (2019)
[M+Na]+140.0627766
predicted
DarkChem Lite v0.1.0
[M+Na]+154.61546
predicted
DeepCCS 1.0 (2019)

Targets

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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 endocytos...
Gene Name
M
Uniprot ID
P21430
Uniprot Name
Matrix protein 2
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:34