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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-03-02 21:33:38 UTC
HMDB IDHMDB15051
Secondary Accession NumbersNone
Metabolite Identification
Common NameAmantadine
DescriptionAn 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
ValueSource
1-AdamantanamineChEBI
1-AdamantylamineChEBI
1-AminoadamantaneChEBI
AmantadinaChEBI
AmantadinumChEBI
AmantidineChEBI
AminoadamantaneChEBI
tricyclo[3.3.1.1(3,7)]Decan-1-amineChEBI
tricyclo[3.3.1.1(3,7)]Decan-1-ylamineChEBI
tricyclo[3.3.1.1(3,7)]Decane-1-amineChEBI
ViregytChEBI
VirosolChEBI
AdamantamineHMDB
AdamantanamineHMDB
AdamantylamineHMDB
Amantadine baseHMDB
Amantadine HCLHMDB
Amantadine hydrochlorideHMDB
AL, amantadinMeSH
AdekinMeSH
Alliance brand OF amantadine hydrochlorideMeSH
AmanMeSH
Amanta-sulfate-azuMeSH
AmantaHCIAZUMeSH
Amantadin alMeSH
Amantadin neuraxpharmMeSH
Amantadin ratiopharmMeSH
Amantadin-neuraxpharmMeSH
Amantadina juventusMeSH
AmantadinratiopharmMeSH
Desitin brand OF amantadine hydrochlorideMeSH
infecto-FluMeSH
Krewel brand OF amantadine hydrochlorideMeSH
Merz brand OF amantadine sulfateMeSH
Novartis brand OF amantadine hydrochlorideMeSH
PMSAmantadineMeSH
Solvay brand OF amantadine hydrochlorideMeSH
Stada brand OF amantadine hydrochlorideMeSH
SymmetrelMeSH
TregorMeSH
AbZ brand OF amantadine hydrochlorideMeSH
Aliud brand OF amantadine sulfateMeSH
Amanta-hci-azuMeSH
Amantadina llorenteMeSH
Azupharma brand OF amantadine hydrochlorideMeSH
Azupharma brand OF amantadine sulfateMeSH
CerebramedMeSH
Gen amantadineMeSH
GenAmantadineMeSH
Hexal brand OF amantadine sulfateMeSH
infecto FluMeSH
Infectopharm brand OF amantadine hydrochlorideMeSH
neuro Hexal brand OF amantadine sulfateMeSH
PMS-AmantadineMeSH
Pharmascience brand OF amantadine hydrochlorideMeSH
SymadineMeSH
Thiemann brand OF amantadine hydrochlorideMeSH
AZU, amantadinMeSH
AmantaMeSH
Amanta hci azuMeSH
Amantadin stadaMeSH
Amantadin-ratiopharmMeSH
Gen-amantadineMeSH
Genpharm brand OF amantadine hydrochlorideMeSH
Hormosan brand OF amantadine sulfateMeSH
Hydrochloride, amantadineMeSH
Juventus, amantadinaMeSH
MantadixMeSH
Stada brand OF amantadine sulfateMeSH
Stada, amantadinMeSH
Sulfate, amantadineMeSH
1 AminoadamantaneMeSH
Amanta sulfate azuMeSH
AmantasulfateazuMeSH
Amantadin azuMeSH
Amantadine sulfateMeSH
AmantadinneuraxpharmMeSH
AmixxMeSH
Ciba geigy brand OF amantadine hydrochlorideMeSH
Ciba-geigy brand OF amantadine hydrochlorideMeSH
Du pont brand OF amantadine hydrochlorideMeSH
EndantadineMeSH
endo Brand OF amantadine hydrochlorideMeSH
InfectoFluMeSH
InfexMeSH
Juventus brand OF amantadine hydrochlorideMeSH
Llorente brand OF amantadine hydrochlorideMeSH
Llorente, amantadinaMeSH
MidantanMeSH
Orion brand OF amantadine hydrochlorideMeSH
PMS AmantadineMeSH
WiregytMeSH
Neuraxpharm brand OF amantadine sulfateMeSH
Ratiopharm brand OF amantadine hydrochlorideMeSH
Chemical FormulaC10H17N
Average Molecular Weight151.2487
Monoisotopic Molecular Weight151.136099549
IUPAC Nameadamantan-1-amine
Traditional Nameamantadine
CAS Registry Number768-94-5
SMILES
NC12CC3CC(CC(C3)C1)C2
InChI Identifier
InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2
InChI KeyDKNWSYNQZKUICI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentMonoalkylamines
Alternative Parents
Substituents
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Analgesics, Non-Narcotic
  • Antiparkinson Agents
  • Antiviral Agents
  • Dopamine Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point180 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.46e-02 g/LNot Available
LogP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.085 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
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
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-44ff981fd5fa6c48df97View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00915
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00915
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-7 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00915
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2045
KEGG Compound IDC06818
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmantadine
NuGOwiki LinkHMDB15051
Metagene LinkHMDB15051
METLIN IDNot Available
PubChem Compound2130
PDB IDNot Available
ChEBI ID2618
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase 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 tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
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. [6891223 ]
General function:
Involved in carboxy-lyase activity
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
Molecular weight:
53893.755
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. [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. [9871440 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
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. [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. [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. 1999;106(5-6):409-21. [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. [9098680 ]
General function:
Involved in ionotropic glutamate receptor activity
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 play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism
Gene Name:
GRIN3A
Uniprot ID:
Q8TCU5
Molecular weight:
125464.1
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. [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. 1999;106(5-6):409-21. [10443547 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
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. [12438524 ]
General function:
Involved in ion 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-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4
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. [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. [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. [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. [15640376 ]
General function:
Involved in ion 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, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular weight:
62564.0
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. [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. [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. [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. [15640376 ]