Amantadine

Identification

Summary

Amantadine is a medication used to treat dyskinesia in Parkinson's patients receiving levodopa, as well as extrapyramidal side effects of medications.

Brand Names
Gocovri, Osmolex
Generic Name
Amantadine
DrugBank Accession Number
DB00915
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 151.2487
Monoisotopic: 151.136099549
Chemical Formula
C10H17N
Synonyms
  • 1-adamantanamine
  • 1-adamantylamine
  • 1-aminoadamantane
  • Amantadina
  • Amantadine
  • Amantadinum
  • Amantidine
  • Aminoadamantane

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofDrug-induced extrapyramidal side effects••••••••••••
Treatment ofDrug-induced extrapyramidal side effects••••••••••••
Adjunct therapy in management ofDyskinesia•••••••••••••••••••• •••••••• •••••••
Adjunct therapy in management ofDyskinesia•••••••••••••••••••• •••••••• •••••••
Prophylaxis ofInfluenza a virus infection••••••••••••
Contraindications & Blackbox Warnings
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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
Humans
ADopamine D2 receptor
agonist
Humans
UNeuronal acetylcholine receptor subunit alpha-7
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-4
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-3
antagonist
Humans
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]
Adverse Effects
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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.

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
AbacavirAmantadine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Amantadine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Amantadine which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Amantadine which could result in a lower serum level and potentially a reduction in efficacy.
AcetylcholineThe risk or severity of adverse effects can be increased when Amantadine is combined with Acetylcholine.
Food Interactions
  • Avoid alcohol.
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Amantadine hydrochlorideM6Q1EO9TD0665-66-7WOLHOYHSEKDWQH-UHFFFAOYSA-N
Amantadine sulfate9921T5P01931377-23-8MYWTWSQFJLXGGQ-UHFFFAOYSA-N
Product Images
International/Other Brands
PK-Merz / Symadine / Viregyt / Virosol
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Amantadine HydrochlorideSolution100 mg/10mLOralPharmaceutical Associates, Inc.2006-10-072007-05-31US flag
Amantadine HydrochlorideSyrup50 mg/5mLOralVintage Pharmaceuticals, LLC2007-05-312007-05-31US flag
EndantadineCapsule100 mgOralBristol Myers Squibb1993-12-312008-04-25Canada flag
Endantadine Cap 100mgCapsule100 mg / capOralDupont Merck Pharma Inc.1993-12-311999-07-20Canada flag
GocovriCapsule, coated pellets137 mg/1OralAdamas Pharma, Llc2017-08-24Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AmantadineCapsule100 mg/1OralAmerican Health Packaging2019-05-01Not applicableUS flag
AmantadineCapsule100 mg/1OralAlembic Pharmaceuticals Inc.2017-06-22Not applicableUS flag
AmantadineTablet100 mg/1OralAlembic Pharmaceuticals Limited2020-10-20Not applicableUS flag
AmantadineTablet100 mg/1OralAlembic Pharmaceuticals Inc.2020-10-20Not applicableUS flag
AmantadineCapsule100 mg/1OralAlembic Pharmaceuticals Limited2017-06-22Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Osmolex ERAmantadine (129 mg/1) + Amantadine (193 mg/1)Kit; Tablet, extended releaseOralVertical Pharmaceuticals, LLC2018-06-012023-03-31US flag
Osmolex ERAmantadine (129 mg/1) + Amantadine (193 mg/1)Kit; Tablet, extended releaseOralVertical Pharmaceuticals, LLC2018-06-012023-03-31US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Gapeam BudibacAmantadine hydrochloride (1 g/1g) + Baclofen (1 g/1g) + Bupivacaine hydrochloride anhydrous (1 g/1g) + Cyclobenzaprine hydrochloride (1 g/1g) + Diclofenac sodium (1 g/1g) + Gabapentin (1 g/1g) + Pentoxifylline (1 g/1g)KitTopicalAlvix Laboratories2014-12-052018-03-08US flag
Innoprax-5Amantadine hydrochloride (8 g/8g) + Baclofen (3 g/3g) + Diclofenac sodium (3 g/3g) + Gabapentin (6 g/6g) + Lidocaine hydrochloride (5 g/5g)KitTopicalAccumix Pharmaceuticals2014-12-152015-07-17US flag

Categories

ATC Codes
N04BB01 — Amantadine
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
adamantanes, primary aliphatic amine (CHEBI:2618)
Affected organisms
  • Humans and other mammals
  • Various viruses

Chemical Identifiers

UNII
BF4C9Z1J53
CAS number
768-94-5
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

References

Synthesis Reference

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

General References
Not Available
Human Metabolome Database
HMDB0015051
KEGG Compound
C06818
PubChem Compound
2130
PubChem Substance
46507081
ChemSpider
2045
BindingDB
50033369
RxNav
620
ChEBI
2618
ChEMBL
CHEMBL660
ZINC
ZINC000000968256
Therapeutic Targets Database
DAP000781
PharmGKB
PA448360
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Amantadine
FDA label
Download (197 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedOtherParkinson's Disease (PD)1
4CompletedTreatmentAtaxia / Chorea / Dystonia / Fatigue / Parkinsonism1
4CompletedTreatmentDelirium / Posttraumatic Confusional State / Traumatic Brain Injury (TBI)1
4CompletedTreatmentParkinson's Disease (PD)2
4CompletedTreatmentTraumas, Brain1

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
  • Anip Acquisition Co.
  • A-S Medication Solutions LLC
  • Banner Pharmacaps Inc.
  • Bristol-Myers Squibb Co.
  • Carolina Medical Products Co.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Endo Pharmaceuticals Inc.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Hi Tech Pharmacal Co. Inc.
  • Lake Erie Medical and Surgical Supply
  • Lannett Co. Inc.
  • Major Pharmaceuticals
  • Mikart Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Patient First Corp.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Association
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Sandoz
  • Southwood Pharmaceuticals
  • Spectrum Pharmaceuticals
  • Tya Pharmaceuticals
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Upsher Smith Laboratories
  • USL Pharma Inc.
  • Vangard Labs Inc.
  • Vintage Pharmaceuticals Inc.
  • Wockhardt Ltd.
Dosage Forms
FormRouteStrength
Tablet, film coatedOral100 MG
SolutionOral
Tablet, film coatedOral200 MG
TabletOral100 MG
SolutionOral10 MG/ML
Capsule, liquid filledOral100 mg/1
CapsuleOral100 mg/1
Capsule, gelatin coatedOral100 mg/1
SolutionOral100 mg/10mL
SolutionOral50 mg/5mL
TabletOral100 1/1
Tablet, film coatedOral100 mg/1
SolutionParenteral200 mg
SyrupOral
SolutionOral500.000 mg
TabletOral
CapsuleOral100 mg / cap
SolutionOral2.500 g
SyrupOral0.500 g
SolutionOral55.000 mg
CapsuleOral
Capsule, coated pelletsOral137 mg/1
Capsule, coated pelletsOral68.5 mg/1
KitTopical
TabletOral100.000 mg
TabletOral
Kit; tablet, extended releaseOral
Tablet, extended releaseOral129 mg/1
Tablet, extended releaseOral161 mg/1
Tablet, extended releaseOral193 mg/1
Tablet, extended releaseOral258 mg/1
SyrupOral50 mg / 5 mL
SolutionParenteral0.4 mg/ml
Tablet, film coatedOral150 MG
SolutionIntravenous40.000 mg
SolutionIntravenous1000 ml
CapsuleOral100 mg
SolutionOral
SyrupOral50 mg/5mL
TabletOral100 mg/1
SyrupOral10 mg / mL
TabletOral200 MG
Capsule, coatedOral100 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)Region
USRE39069No2006-04-182018-05-29US flag
US8895616No2014-11-252025-11-23US flag
US8895617No2014-11-252025-11-23US flag
US8741343No2014-06-032030-12-02US flag
US8895615No2014-11-252025-11-23US flag
US8796337No2014-08-052025-11-23US flag
US8389578No2013-03-052028-01-22US flag
US8895618No2014-11-252025-11-23US flag
US8895614No2014-11-252025-11-23US flag
US8889740No2014-11-182025-11-23US flag
US9867792No2018-01-162030-12-02US flag
US9867793No2018-01-162030-12-02US flag
US9867791No2018-01-162030-12-02US flag
US9877933No2018-01-302030-12-02US flag
US8574626No2013-11-052025-11-28US flag
US8252331No2012-08-282030-03-13US flag
US10154971No2018-12-182034-12-04US flag
US10213393No2019-02-262038-02-15US flag
US10213394No2019-02-262038-02-15US flag
US10500171No2019-12-102038-02-15US flag
US10500172No2019-12-102038-02-15US flag
US10500170No2019-12-102038-02-15US flag
US10512617No2019-12-242038-02-15US flag
US10646456No2020-05-122034-06-17US flag
US9072697No2015-07-072025-11-23US flag
US8987333No2015-03-242025-11-23US flag
US11077073No2021-08-032038-08-23US flag
US11065213No2021-07-202038-08-23US flag
US11197835No2021-12-142030-12-02US flag

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-MSsplash10-0udi-0900000000-ffe93d952abd2a39e06e
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
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-4a2a714e62109426be5e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-d0e888c03830e640b41b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-bcf7768eabf97f17b19c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-d0e888c03830e640b41b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-3db9299732ed5bbae188
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-24a79a88cbf215779aaf
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
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]-128.8406874
predicted
DarkChem Lite v0.1.0
[M-H]-128.7937874
predicted
DarkChem Lite v0.1.0
[M-H]-137.47629
predicted
DeepCCS 1.0 (2019)
[M+H]+129.5415874
predicted
DarkChem Lite v0.1.0
[M+H]+129.5081874
predicted
DarkChem Lite v0.1.0
[M+H]+139.87221
predicted
DeepCCS 1.0 (2019)
[M+Na]+128.9830874
predicted
DarkChem Lite v0.1.0
[M+Na]+148.8043
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
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. [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. 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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. doi:10.1007/s00415-006-3004-8 [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Toxic substance binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da
References
  1. Matsubayashi H, Swanson KL, Albuquerque EX: Amantadine inhibits nicotinic acetylcholine receptor function in hippocampal neurons. J Pharmacol Exp Ther. 1997 May;281(2):834-44. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Matsubayashi H, Swanson KL, Albuquerque EX: Amantadine inhibits nicotinic acetylcholine receptor function in hippocampal neurons. J Pharmacol Exp Ther. 1997 May;281(2):834-44. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA3
Uniprot ID
P32297
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-3
Molecular Weight
57479.54 Da
References
  1. Matsubayashi H, Swanson KL, Albuquerque EX: Amantadine inhibits nicotinic acetylcholine receptor function in hippocampal neurons. J Pharmacol Exp Ther. 1997 May;281(2):834-44. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. BACTRIM (sulfamethoxazole and trimethoprim) FDA Label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Li L, Song F, Tu M, Wang K, Zhao L, Wu X, Zhou H, Xia Z, Jiang H: In vitro interaction of clopidogrel and its hydrolysate with OCT1, OCT2 and OAT1. Int J Pharm. 2014 Apr 25;465(1-2):5-10. doi: 10.1016/j.ijpharm.2014.02.003. Epub 2014 Feb 11. [Article]
  2. Harrach S, Schmidt-Lauber C, Pap T, Pavenstadt H, Schlatter E, Schmidt E, Berdel WE, Schulze U, Edemir B, Jeromin S, Haferlach T, Ciarimboli G, Bertrand J: MATE1 regulates cellular uptake and sensitivity to imatinib in CML patients. Blood Cancer J. 2016 Sep 16;6:e470. doi: 10.1038/bcj.2016.79. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48