Identification

Name
Amantadine
Accession Number
DB00915  (APRD00787)
Type
Small Molecule
Groups
Approved
Description

An antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. The mechanisms of its effects in movement disorders are not well understood but probably reflect an increase in synthesis and release of dopamine, with perhaps some inhibition of dopamine uptake. [PubChem]

Structure
Thumb
Synonyms
  • 1-adamantanamine
  • 1-adamantylamine
  • 1-aminoadamantane
  • Amantadina
  • Amantadine
  • Amantadinum
  • Amantidine
  • Aminoadamantane
  • Tricyclo[3.3.1.1(3,7)]decan-1-amine
  • Tricyclo[3.3.1.1(3,7)]decan-1-ylamine
  • Tricyclo[3.3.1.1(3,7)]decane-1-amine
  • Viregyt
  • Virosol
Product Ingredients
IngredientUNIICASInChI Key
Amantadine hydrochlorideM6Q1EO9TD0665-66-7WOLHOYHSEKDWQH-UHFFFAOYSA-N
Amantadine sulfate9921T5P01931377-23-8MYWTWSQFJLXGGQ-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-amantadine Hydrochloride Capsules-100mgCapsule100 mgOralDominion Pharmacal1998-03-20Not applicableCanada
EndantadineCapsule100 mgOralBristol Myers Squibb1993-12-312008-04-25Canada
Endantadine Cap 100mgCapsule100 mgOralDupont Merck Pharma Inc.1993-12-311999-07-20Canada
GocovriCapsule, coated pellets137 mg/1OralAdamas Pharma, Llc2017-08-24Not applicableUs
GocovriCapsule, coated pellets68.5 mg/1OralAdamas Pharma, Llc2017-08-24Not applicableUs
Med-amantidine - Cap 100mgCapsule100 mgOralMedican Pharma Incorporated1996-07-302011-03-29Canada
Mylan-amantadineCapsule100 mgOralMylan Pharmaceuticals1994-12-312016-06-28Canada
Pdp-amantadine Hydrochloride CapsulesCapsule100 mgOralPendopharm Division Of De Pharmascience Inc1992-12-31Not applicableCanada
Pdp-amantadine Hydrochloride SyrupSyrup10 mgOralPendopharm Division Of De Pharmascience Inc1993-12-31Not applicableCanada
PHL-amantadineCapsule100 mgOralPharmel Inc1998-09-032009-10-26Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmantadineCapsule100 mg/1OralAlembic Pharmaceuticals Limited2017-06-22Not applicableUs
AmantadineCapsule100 mg/1OralAlembic Pharmaceuticals Limited2017-06-22Not applicableUs
Amantadine HClCapsule, liquid filled100 mg/1OralBanner Life Sciences Llc.2015-09-07Not applicableUs
Amantadine HClCapsule100 mg/1OralRebel Distributors2008-11-01Not applicableUs
Amantadine HClCapsule, liquid filled100 mg/1OralAv Kare, Inc.2013-08-07Not applicableUs
Amantadine HClCapsule100 mg/1Oralbryant ranch prepack2008-11-01Not applicableUs
Amantadine HClCapsule, liquid filled100 mg/1OralBionpharma Inc.2016-08-15Not applicableUs
Amantadine HClCapsule, liquid filled100 mg/1OralBanner Pharmacaps2012-11-01Not applicableUs
Amantadine HClCapsule, liquid filled100 mg/1OralPreferreed Pharmaceuticals Inc.2013-12-20Not applicableUs
Amantadine HClCapsule, liquid filled100 mg/1OralAv Pak2014-03-28Not applicableUs
International/Other Brands
PK-Merz / Symadine / Symmetrel (Endo Pharmaceuticals)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Gapeam BudibacAmantadine hydrochloride + Baclofen + Bupivacaine hydrochloride + Cyclobenzaprine Hydrochloride + Diclofenac sodium + Gabapentin + PentoxifyllineKitTopicalAlvix Laboratories2014-12-05Not applicableUs
Categories
UNII
BF4C9Z1J53
CAS number
768-94-5
Weight
Average: 151.2487
Monoisotopic: 151.136099549
Chemical Formula
C10H17N
InChI Key
DKNWSYNQZKUICI-UHFFFAOYSA-N
InChI
InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2
IUPAC Name
adamantan-1-amine
SMILES
NC12CC3CC(CC(C3)C1)C2

Pharmacology

Indication

For the chemoprophylaxis, prophylaxis, and treatment of signs and symptoms of infection caused by various strains of influenza A virus. Also for the treatment of parkinsonism and drug-induced extrapyramidal reactions.

Structured Indications
Pharmacodynamics

Amantadine is an antiviral drug which also acts as an antiparkinson agent, for which it is usually combined with L-DOPA when L-DOPA responses decline (probably due to tolerance). It is a derivate of adamantane, like a similar drug rimantadine. The mechanism of action of amantadine in the treatment of Parkinson's disease and drug-induced extrapyramidal reactions is not known. It has been shown to cause an increase in dopamine release in the animal brain, and does not possess anticholinergic activity.

Mechanism of action

The mechanism of its antiparkinsonic effect is not fully understood, but it appears to be releasing dopamine from the nerve endings of the brain cells, together with stimulation of norepinephrine response. It also has NMDA receptor antagonistic effects. The antiviral mechanism seems to be unrelated. The drug interferes with a viral protein, M2 (an ion channel), which is needed for the viral particle to become "uncoated" once it is taken inside the cell by endocytosis.

TargetActionsOrganism
AMatrix protein 2
inhibitor
Influenza A virus (strain A/Ann Arbor/6/1960 H2N2)
AGlutamate receptor ionotropic, NMDA 3A
antagonist
Human
AD(2) dopamine receptor
agonist
Human
Absorption

Amantadine is well absorbed orally from the gastrointestinal tract.

Volume of distribution
  • 3 to 8 L/kg [healthy subjects]
Protein binding

Approximately 67% bound to plasma proteins over a concentration range of 0.1 to 2.0 µg/mL.

Metabolism

No appreciable metabolism, although negligible amounts of an acetyl metabolite have been identified.

Route of elimination

It is primarily excreted unchanged in the urine by glomerular filtration and tubular secretion.

Half life

Mean half-lives ranged from 10 to 14 hours, however renal function impairment causes a severe increase in half life to 7 to 10 days.

Clearance
  • 0.2 - 0.3 L/hr/kg
  • 0.10 +/- 0.04 L/hr/kg [healthy, elderly male]
Toxicity

Deaths have been reported from overdose with amantadine. The lowest reported acute lethal dose was 2 grams. Drug overdose has resulted in cardiac, respiratory, renal or central nervous system toxicity. Cardiac dysfunction includes arrhythmia, tachycardia and hypertension. Pulmonary edema and respiratory distress (including ARDS) have been reported. Renal dysfunction including increased BUN, decreased creatinine clearance and renal insufficiency can occur. Central nervous system effects that have been reported include insomnia, anxiety, aggressive behavior, hypertonia, hyperkinesia, tremor, confusion, disorientation, depersonalization, fear, delirium, hallucination, psychotic reactions, lethargy, somnolence and coma. Seizures may be exacerbated in patients with prior history of seizure disorders. Hyperthermia has also been observed in cases where a drug overdose has occurred.

Affected organisms
  • Humans and other mammals
  • Various viruses
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Amantadine.Approved
AmiodaroneAmantadine may increase the QTc-prolonging activities of Amiodarone.Approved, Investigational
AmisulprideThe therapeutic efficacy of Amisulpride can be decreased when used in combination with Amantadine.Approved, Investigational
AnagrelideAmantadine may increase the QTc-prolonging activities of Anagrelide.Approved
AripiprazoleThe therapeutic efficacy of Amantadine can be decreased when used in combination with Aripiprazole.Approved, Investigational
Arsenic trioxideAmantadine may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherAmantadine may increase the QTc-prolonging activities of Artemether.Approved
AsenapineAmantadine may increase the QTc-prolonging activities of Asenapine.Approved
AzithromycinAmantadine may increase the QTc-prolonging activities of Azithromycin.Approved
BedaquilineAmantadine may increase the QTc-prolonging activities of Bedaquiline.Approved
BlonanserinThe therapeutic efficacy of Amantadine can be decreased when used in combination with Blonanserin.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Amantadine.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Amantadine.Approved
BupropionThe risk or severity of adverse effects can be increased when Amantadine is combined with Bupropion.Approved
CariprazineThe therapeutic efficacy of Amantadine can be decreased when used in combination with Cariprazine.Approved
CeritinibAmantadine may increase the QTc-prolonging activities of Ceritinib.Approved
ChloroquineAmantadine may increase the QTc-prolonging activities of Chloroquine.Approved, Vet Approved
ChlorpromazineThe therapeutic efficacy of Chlorpromazine can be decreased when used in combination with Amantadine.Approved, Vet Approved
ChlorprothixeneThe therapeutic efficacy of Chlorprothixene can be decreased when used in combination with Amantadine.Approved, Investigational, Withdrawn
CiprofloxacinAmantadine may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideAmantadine may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramAmantadine may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinAmantadine may increase the QTc-prolonging activities of Clarithromycin.Approved
ClozapineThe therapeutic efficacy of Amantadine can be decreased when used in combination with Clozapine.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Amantadine.Approved
CrizotinibAmantadine may increase the QTc-prolonging activities of Crizotinib.Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Amantadine.Approved
DisopyramideAmantadine may increase the QTc-prolonging activities of Disopyramide.Approved
DofetilideAmantadine may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronAmantadine may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneAmantadine may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Amantadine.Approved, Investigational
DronedaroneAmantadine may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolThe therapeutic efficacy of Droperidol can be decreased when used in combination with Amantadine.Approved, Vet Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Amantadine.Approved
EliglustatAmantadine may increase the QTc-prolonging activities of Eliglustat.Approved
ErythromycinAmantadine may increase the QTc-prolonging activities of Erythromycin.Approved, Vet Approved
EscitalopramAmantadine may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
EthanolEthanol may increase the central nervous system depressant (CNS depressant) activities of Amantadine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Amantadine.Approved
FlecainideAmantadine may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FluoxetineAmantadine may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolAmantadine may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FluphenazineThe therapeutic efficacy of Fluphenazine can be decreased when used in combination with Amantadine.Approved
Gadobenic acidAmantadine may increase the QTc-prolonging activities of Gadobenic acid.Approved
GemifloxacinAmantadine may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GlycopyrroniumAmantadine may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational, Vet Approved
GoserelinAmantadine may increase the QTc-prolonging activities of Goserelin.Approved
GranisetronAmantadine may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
HaloperidolThe therapeutic efficacy of Haloperidol can be decreased when used in combination with Amantadine.Approved
IbutilideAmantadine may increase the QTc-prolonging activities of Ibutilide.Approved
IloperidoneAmantadine may increase the QTc-prolonging activities of Iloperidone.Approved
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Amantadine.Approved
LenvatinibAmantadine may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideAmantadine may increase the QTc-prolonging activities of Leuprolide.Approved, Investigational
LevofloxacinAmantadine may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LopinavirAmantadine may increase the QTc-prolonging activities of Lopinavir.Approved
LoxapineThe therapeutic efficacy of Loxapine can be decreased when used in combination with Amantadine.Approved
LumateperoneThe therapeutic efficacy of Amantadine can be decreased when used in combination with Lumateperone.Investigational
LumefantrineAmantadine may increase the QTc-prolonging activities of Lumefantrine.Approved
LurasidoneThe therapeutic efficacy of Amantadine can be decreased when used in combination with Lurasidone.Approved
MelperoneThe therapeutic efficacy of Amantadine can be decreased when used in combination with Melperone.Approved, Investigational
MemantineThe risk or severity of adverse effects can be increased when Amantadine is combined with Memantine.Approved, Investigational
MesoridazineThe therapeutic efficacy of Mesoridazine can be decreased when used in combination with Amantadine.Approved, Investigational
MethadoneAmantadine may increase the QTc-prolonging activities of Methadone.Approved
MethotrimeprazineThe therapeutic efficacy of Methotrimeprazine can be decreased when used in combination with Amantadine.Approved
MethylphenidateThe risk or severity of adverse effects can be increased when Methylphenidate is combined with Amantadine.Approved, Investigational
MetoclopramideThe therapeutic efficacy of Amantadine can be decreased when used in combination with Metoclopramide.Approved, Investigational
MifepristoneMifepristone may increase the QTc-prolonging activities of Amantadine.Approved, Investigational
MolindoneThe therapeutic efficacy of Molindone can be decreased when used in combination with Amantadine.Approved
MoxifloxacinAmantadine may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Amantadine.Approved
NilotinibAmantadine may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
OfloxacinAmantadine may increase the QTc-prolonging activities of Ofloxacin.Approved
OlanzapineThe therapeutic efficacy of Amantadine can be decreased when used in combination with Olanzapine.Approved, Investigational
OndansetronAmantadine may increase the QTc-prolonging activities of Ondansetron.Approved
PaliperidoneAmantadine may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatAmantadine may increase the QTc-prolonging activities of Panobinostat.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Amantadine.Approved
PentamidineAmantadine may increase the QTc-prolonging activities of Pentamidine.Approved
PerflutrenAmantadine may increase the QTc-prolonging activities of Perflutren.Approved
PerospironeThe therapeutic efficacy of Amantadine can be decreased when used in combination with Perospirone.Approved
PerphenazineThe therapeutic efficacy of Perphenazine can be decreased when used in combination with Amantadine.Approved
PimavanserinThe therapeutic efficacy of Amantadine can be decreased when used in combination with Pimavanserin.Approved, Investigational
PimozideAmantadine may increase the QTc-prolonging activities of Pimozide.Approved
PrimaquineAmantadine may increase the QTc-prolonging activities of Primaquine.Approved
ProcainamideAmantadine may increase the QTc-prolonging activities of Procainamide.Approved
ProchlorperazineThe therapeutic efficacy of Prochlorperazine can be decreased when used in combination with Amantadine.Approved, Vet Approved
PromazineThe therapeutic efficacy of Promazine can be decreased when used in combination with Amantadine.Approved, Vet Approved
PropafenoneAmantadine may increase the QTc-prolonging activities of Propafenone.Approved
PropericiazineThe therapeutic efficacy of Propericiazine can be decreased when used in combination with Amantadine.Approved
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Amantadine.Approved
QuetiapineAmantadine may increase the QTc-prolonging activities of Quetiapine.Approved
QuinidineAmantadine may increase the QTc-prolonging activities of Quinidine.Approved
QuinineAmantadine may increase the QTc-prolonging activities of Quinine.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Amantadine.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Amantadine.Approved, Investigational
RisperidoneThe therapeutic efficacy of Amantadine can be decreased when used in combination with Risperidone.Approved, Investigational
RP5063The therapeutic efficacy of Amantadine can be decreased when used in combination with RP5063.Investigational
SaquinavirAmantadine may increase the QTc-prolonging activities of Saquinavir.Approved, Investigational
SertindoleThe therapeutic efficacy of Amantadine can be decreased when used in combination with Sertindole.Approved, Investigational, Withdrawn
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Amantadine.Approved
SotalolAmantadine may increase the QTc-prolonging activities of Sotalol.Approved
SulfisoxazoleAmantadine may increase the QTc-prolonging activities of Sulfisoxazole.Approved, Vet Approved
TelavancinAmantadine may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinAmantadine may increase the QTc-prolonging activities of Telithromycin.Approved
TetrabenazineAmantadine may increase the QTc-prolonging activities of Tetrabenazine.Approved
ThioproperazineThe therapeutic efficacy of Thioproperazine can be decreased when used in combination with Amantadine.Approved
ThioridazineAmantadine may increase the QTc-prolonging activities of Thioridazine.Approved, Withdrawn
ThiothixeneThe therapeutic efficacy of Thiothixene can be decreased when used in combination with Amantadine.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Amantadine.Approved, Investigational
ToremifeneAmantadine may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
TrifluoperazineThe therapeutic efficacy of Trifluoperazine can be decreased when used in combination with Amantadine.Approved
TrimethoprimThe risk or severity of adverse effects can be increased when Trimethoprim is combined with Amantadine.Approved, Vet Approved
VandetanibAmantadine may increase the QTc-prolonging activities of Vandetanib.Approved
VemurafenibAmantadine may increase the QTc-prolonging activities of Vemurafenib.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Amantadine.Approved, Investigational
ZiprasidoneAmantadine may increase the QTc-prolonging activities of Ziprasidone.Approved
ZotepineThe therapeutic efficacy of Amantadine can be decreased when used in combination with Zotepine.Approved, Investigational
ZuclopenthixolAmantadine may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

References

Synthesis Reference

Haaf, W.; U.S. Patent 3,152,180; October 6, 1964; assigned to Studiengesellschaft Kohle mbH, Germany.

General References
Not Available
External Links
Human Metabolome Database
HMDB15051
KEGG Compound
C06818
PubChem Compound
2130
PubChem Substance
46507081
ChemSpider
2045
BindingDB
50033369
ChEBI
2618
ChEMBL
CHEMBL660
Therapeutic Targets Database
DAP000781
PharmGKB
PA448360
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Amantadine
ATC Codes
N04BB01 — Amantadine
AHFS Codes
  • 08:18.04 — Adamantanes
  • 28:36.04 — Adamantanes
FDA label
Download (197 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedDiagnosticCocaine-Related Disorders / Substance-Related Disorders1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentMood Disorders With Psychotic Features / Psychotic Disorder NOS / Schizoaffective Disorders / Schizophrenic Disorders / Schizophreniform Disorder1
1, 2CompletedTreatmentFlu caused by Influenza1
1, 2Unknown StatusEducational/Counseling/TrainingHyperalgesia / Pain / Prostate Cancer1
2CompletedTreatmentChorea / Huntington's Disease (HD)1
2CompletedTreatmentCocaine-Related Disorders2
2CompletedTreatmentDisseminated Sclerosis / Walking Impairment1
2CompletedTreatmentFlu caused by Influenza2
2CompletedTreatmentType 2 Diabetes Mellitus1
2RecruitingDiagnosticCancers1
2RecruitingTreatmentAnoxia / Comatose / Heart Arrest1
2RecruitingTreatmentParkinson's Disease (PD)1
2TerminatedTreatmentInfluenza A Infection1
2TerminatedTreatmentParkinson's Disease (PD) / Perioperative Care1
2Unknown StatusTreatmentAttention Deficit Hyperactivity Disorder (ADHD)1
2, 3CompletedTreatmentDyskinesias / Levodopa Induced Dyskinesia (LID) / Parkinson's Disease (PD)1
2, 3CompletedTreatmentTraumatic Brain Injury (TBI)1
2, 3RecruitingPreventionEffect of Laryngoscopy and Tracheal Intubation1
3Active Not RecruitingTreatmentDyskinesias / Levodopa Induced Dyskinesia (LID) / Parkinson's Disease (PD)1
3CompletedPreventionSchizoaffective Disorders / Schizophrenic Disorders1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
3CompletedTreatmentDyskinesias / Levodopa Induced Dyskinesia (LID) / Parkinson's Disease (PD)1
3CompletedTreatmentDyskinesias / Levodopa-Induced Dyskinesia (LID) / Parkinson's Disease (PD)1
3CompletedTreatmentHCV Infections / Hepatitis C, Chronic1
3RecruitingTreatmentFatigue in Multiple Sclerosis1
3RecruitingTreatmentLevodopa Induced Dyskinesia (LID) / Parkinson's Disease (PD)1
3RecruitingTreatmentLevodopa Induced Dyskinesias (LID) / Parkinson's Disease (PD)1
3TerminatedTreatmentHepatitis C, Chronic1
3TerminatedTreatmentParkinson's Disease (PD)1
3Unknown StatusTreatmentSchizophrenic Disorders1
4CompletedNot AvailableParkinson's Disease (PD)1
4CompletedTreatmentAtaxia / Chorea / Dystonias / Parkinsonism / Tiredness1
4CompletedTreatmentParkinson's Disease (PD)1
4RecruitingTreatmentTraumatic Brain Injury (TBI)1
4TerminatedTreatmentDementias1
4TerminatedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
4Unknown StatusTreatmentDelirium / Posttraumatic Confusional State / Traumatic Brain Injury (TBI)1
Not AvailableActive Not RecruitingTreatmentTraumatic Brain Injury (TBI)1
Not AvailableCompletedDiagnosticHealthy Metabolism1
Not AvailableCompletedTreatmentAggressive Behavior / Brain Injury1
Not AvailableCompletedTreatmentAggressive Behavior / Irritability / Traumatic Brain Injury (TBI)1
Not AvailableNot Yet RecruitingNot AvailableAcquired Brain Injury / Comatose / Minimally Conscious State / Persistent Vegetative State / Traumatic Brain Injury (TBI)1
Not AvailableRecruitingNot AvailableAtypical Parkinson Disease / Corticobasal Degeneration / Gait, Frontal / Multiple System Atrophy (MSA) / Parkinson's Disease (PD) / Parkinsonian Disorders / Progressive Supranuclear Palsy (PSP)1
Not AvailableTerminatedBasic ScienceTraumatic Brain Injury (TBI)1
Not AvailableTerminatedTreatmentParkinson's Disease (PD)1
Not AvailableUnknown StatusTreatmentParkinson's Disease (PD)1

Pharmacoeconomics

Manufacturers
  • Actavis totowa llc
  • Banner pharmacaps inc
  • Sandoz inc
  • Usl pharma inc
  • Watson laboratories inc
  • Solvay pharmaceuticals
  • Endo pharmaceuticals inc
  • Actavis mid atlantic llc
  • Carolina medical products co
  • Hi tech pharmacal co inc
  • Mikart inc
  • Pharmaceutical assoc inc div beach products
  • Silarx pharmaceuticals inc
  • Teva pharmaceuticals usa
  • Vintage pharmaceuticals llc
  • Wockhardt eu operations (swiss) ag
Packagers
Dosage forms
FormRouteStrength
Capsule, liquid filledOral100 mg/1
CapsuleOral100 mg/1
Capsule, gelatin coatedOral100 mg/1
SolutionOral50 mg/5mL
SyrupOral50 mg/5mL
TabletOral100 mg/1
KitTopical
Capsule, coated pelletsOral137 mg/1
Capsule, coated pelletsOral68.5 mg/1
CapsuleOral100 mg
SyrupOral10 mg
Prices
Unit descriptionCostUnit
Symmetrel 50 mg/5ml Syrup 480ml Bottle151.46USD bottle
Amantadine hcl powder6.7USD g
Symmetrel 100 mg tablet1.45USD tablet
Amantadine HCl 100 mg tablet1.37USD tablet
Amantadine 100 mg tablet1.32USD tablet
Amantadine HCl 100 mg capsule0.78USD capsule
Mylan-Amantadine 100 mg Capsule0.54USD capsule
Pms-Amantadine Hydrochloride 100 mg Capsule0.54USD capsule
Amantadine HCl 50 mg/5ml Syrup0.16USD ml
Pms-Amantadine Hydrochloride 10 mg/ml Syrup0.09USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8895616No2005-11-232025-11-23Us
US8895617No2005-11-232025-11-23Us
US8741343No2010-12-022030-12-02Us
US8895615No2005-11-232025-11-23Us
US8796337No2005-11-232025-11-23Us
US8389578No2008-01-222028-01-22Us
US8895618No2005-11-232025-11-23Us
US8895614No2005-11-232025-11-23Us
US8889740No2005-11-232025-11-23Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)180-192Haaf, W.; U.S. Patent 3,152,180; October 6, 1964; assigned to Studiengesellschaft Kohle mbH, Germany.
water solubility6290 mg/L (freely soluble)Not Available
logP2.44HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0846 mg/mLALOGPS
logP2.53ALOGPS
logP1.47ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)10.71ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.54 m3·mol-1ChemAxon
Polarizability17.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9903
Blood Brain Barrier+0.9769
Caco-2 permeable+0.6248
P-glycoprotein substrateNon-substrate0.7275
P-glycoprotein inhibitor INon-inhibitor0.9277
P-glycoprotein inhibitor IINon-inhibitor0.8549
Renal organic cation transporterNon-inhibitor0.7474
CYP450 2C9 substrateNon-substrate0.8306
CYP450 2D6 substrateNon-substrate0.7092
CYP450 3A4 substrateNon-substrate0.6561
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5886
Ames testNon AMES toxic0.7836
CarcinogenicityNon-carcinogens0.7647
BiodegradationNot ready biodegradable0.9456
Rat acute toxicity2.2564 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9779
hERG inhibition (predictor II)Non-inhibitor0.8695
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.71 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1910000000-c4908efe87e5cdf2ba74
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1910000000-8b7366cc494bf757bb81
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-01b9-6910000000-e6fd5b29f51169a772e5
Mass Spectrum (Electron Ionization)MSsplash10-0006-9100000000-44ff981fd5fa6c48df97
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f79-0900000000-b3511c6e5de6fce544c6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f79-0900000000-ca740a06e33d4850b211
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-f1084780a2940c5afd1b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-a083f7fdcbb679c2996a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-2900000000-496b35f0cfba5aa930ed
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-7900000000-e37809d5efe023b0382d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-1a8aac6647f0187ebdf9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0900000000-88a4152a7398da21333c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-1900000000-76e73b05fc9ac0bdc170
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-002u-9600000000-048cdcfd022184f574b6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004l-9000000000-8bc5ffed5487b0edffaf
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-4aa7b04aaac47d693e8d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udr-0900000000-815d4b207b027466d755
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-7ce8af9197b4d35ecffd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-278de51184b1c34ed88f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-1a9620db53d99baf9c05
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-1a9620db53d99baf9c05
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f79-1900000000-f49f767b2078c543faad
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

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
Organopnictogen compound / Hydrocarbon derivative / Primary aliphatic amine / Aliphatic homopolycyclic compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
adamantanes, primary aliphatic amine (CHEBI:2618)

Targets

Kind
Protein
Organism
Influenza A virus (strain A/Ann Arbor/6/1960 H2N2)
Pharmacological action
Yes
Actions
Inhibitor
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. Wang C, Takeuchi K, Pinto LH, Lamb RA: Ion channel activity of influenza A virus M2 protein: characterization of the amantadine block. J Virol. 1993 Sep;67(9):5585-94. [PubMed:7688826]
  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. Wang J, Cady SD, Balannik V, Pinto LH, DeGrado WF, Hong M: Discovery of spiro-piperidine inhibitors and their modulation of the dynamics of the M2 proton channel from influenza A virus. J Am Chem Soc. 2009 Jun 17;131(23):8066-76. doi: 10.1021/ja900063s. [PubMed:19469531]
  4. Beigel J, Bray M: Current and future antiviral therapy of severe seasonal and avian influenza. Antiviral Res. 2008 Apr;78(1):91-102. doi: 10.1016/j.antiviral.2008.01.003. Epub 2008 Feb 4. [PubMed:18328578]
  5. 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:12972146]
  6. Salom D, Hill BR, Lear JD, DeGrado WF: pH-dependent tetramerization and amantadine binding of the transmembrane helix of M2 from the influenza A virus. Biochemistry. 2000 Nov 21;39(46):14160-70. [PubMed:11087364]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein phosphatase 2a binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May ...
Gene Name
GRIN3A
Uniprot ID
Q8TCU5
Uniprot Name
Glutamate receptor ionotropic, NMDA 3A
Molecular Weight
125464.07 Da
References
  1. Blanpied TA, Clarke RJ, Johnson JW: Amantadine inhibits NMDA receptors by accelerating channel closure during channel block. J Neurosci. 2005 Mar 30;25(13):3312-22. [PubMed:15800186]
  2. Hesselink MB, De Boer AG, Breimer DD, Danysz W: Adaptations of NMDA and dopamine D2, but not of muscarinic receptors following 14 days administration of uncompetitive NMDA receptor antagonists. J Neural Transm (Vienna). 1999;106(5-6):409-21. [PubMed:10443547]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Tomitaka S, Hashimoto K, Narita N, Minabe Y, Tamura A: Amantadine induces c-fos in rat striatum: reversal with dopamine D1 and NMDA receptor antagonists. Eur J Pharmacol. 1995 Oct 16;285(2):207-11. [PubMed:8566141]
  2. Ameri A: Effects of the Aconitum alkaloid songorine on synaptic transmission and paired-pulse facilitation of CA1 pyramidal cells in rat hippocampal slices. Br J Pharmacol. 1998 Oct;125(3):461-8. [PubMed:9806328]
  3. Hesselink MB, De Boer AG, Breimer DD, Danysz W: Adaptations of NMDA and dopamine D2, but not of muscarinic receptors following 14 days administration of uncompetitive NMDA receptor antagonists. J Neural Transm (Vienna). 1999;106(5-6):409-21. [PubMed:10443547]
  4. Cousins MS, Carriero DL, Salamone JD: Tremulous jaw movements induced by the acetylcholinesterase inhibitor tacrine: effects of antiparkinsonian drugs. Eur J Pharmacol. 1997 Mar 19;322(2-3):137-45. [PubMed:9098680]
  5. doi:10.1007/s00415-006-3004-8 [Link]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name
DDC
Uniprot ID
P20711
Uniprot Name
Aromatic-L-amino-acid decarboxylase
Molecular Weight
53925.815 Da
References
  1. Li XM, Juorio AV, Qi J, Boulton AA: Amantadine increases aromatic L-amino acid decarboxylase mRNA in PC12 cells. J Neurosci Res. 1998 Aug 15;53(4):490-3. [PubMed:9710269]
  2. Fisher A, Biggs CS, Starr MS: Effects of glutamate antagonists on the activity of aromatic L-amino acid decarboxylase. Amino Acids. 1998;14(1-3):43-9. [PubMed:9871440]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Wesemann W, Ekenna O: Effect of 1-aminoadamantanes on the MAO activity in brain, liver, and kidney of the rat. Arzneimittelforschung. 1982;32(10):1241-3. [PubMed:6891223]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365]
  2. Busch AE, Karbach U, Miska D, Gorboulev V, Akhoundova A, Volk C, Arndt P, Ulzheimer JC, Sonders MS, Baumann C, Waldegger S, Lang F, Koepsell H: Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52. [PubMed:9687576]
  3. Goralski KB, Lou G, Prowse MT, Gorboulev V, Volk C, Koepsell H, Sitar DS: The cation transporters rOCT1 and rOCT2 interact with bicarbonate but play only a minor role for amantadine uptake into rat renal proximal tubules. J Pharmacol Exp Ther. 2002 Dec;303(3):959-68. [PubMed:12438515]
  4. Ishiguro N, Saito A, Yokoyama K, Morikawa M, Igarashi T, Tamai I: Transport of the dopamine D2 agonist pramipexole by rat organic cation transporters OCT1 and OCT2 in kidney. Drug Metab Dispos. 2005 Apr;33(4):495-9. Epub 2005 Jan 7. [PubMed:15640376]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755]
  2. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880]
  3. Goralski KB, Lou G, Prowse MT, Gorboulev V, Volk C, Koepsell H, Sitar DS: The cation transporters rOCT1 and rOCT2 interact with bicarbonate but play only a minor role for amantadine uptake into rat renal proximal tubules. J Pharmacol Exp Ther. 2002 Dec;303(3):959-68. [PubMed:12438515]
  4. Ishiguro N, Saito A, Yokoyama K, Morikawa M, Igarashi T, Tamai I: Transport of the dopamine D2 agonist pramipexole by rat organic cation transporters OCT1 and OCT2 in kidney. Drug Metab Dispos. 2005 Apr;33(4):495-9. Epub 2005 Jan 7. [PubMed:15640376]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33