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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (3) Show 7 proteins XML

enzymes (4)transporters (3) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015051

Secondary Accession Numbers

HMDB15051

Metabolite Identification

Common Name

Amantadine

Description

Amantadine, also known as 1-adamantanamine or 1-aminoadamantane, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Amantadine is a drug which is used 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. 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. 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. Amantadine is a very strong basic compound (based on its pKa). In humans, amantadine is involved in loratadine h1-antihistamine action. Amantadine is a potentially toxic compound. Pulmonary edema and respiratory distress (including ARDS) have been reported.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0015051
HETATM    1  N1  UNL     1       2.606   0.006   0.780  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.203   0.074   0.368  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.318  -0.392   1.532  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.114  -0.363   1.099  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.279  -1.343  -0.063  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.439  -0.898  -1.218  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.710   0.505  -1.667  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.623   1.440  -0.485  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.569   0.977   0.599  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.780   1.467   0.035  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.018  -0.911  -0.740  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.144  -0.108  -0.127  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.709  -0.919   1.277  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.593  -1.465   1.686  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.499   0.223   2.429  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.759  -0.658   1.936  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.832  -2.306   0.311  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.338  -1.512  -0.309  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.588  -1.574  -2.059  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.639   0.642  -2.222  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.138   0.779  -2.363  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.941   2.454  -0.810  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.707   1.729   1.371  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.575   0.818   0.121  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.750   2.037   1.010  1.00  0.00           H  
HETATM   26  H15 UNL     1       1.476   2.012  -0.617  1.00  0.00           H  
HETATM   27  H16 UNL     1       1.159  -1.934  -0.297  1.00  0.00           H  
HETATM   28  H17 UNL     1       1.719  -0.781  -1.578  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3   10   11
CONECT    3    4   14   15
CONECT    4    5    9   16
CONECT    5    6   17   18
CONECT    6    7   11   19
CONECT    7    8   20   21
CONECT    8    9   10   22
CONECT    9   23   24
CONECT   10   25   26
CONECT   11   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Adamantanamine	ChEBI
1-Adamantylamine	ChEBI
1-Aminoadamantane	ChEBI
Amantadina	ChEBI
Amantadinum	ChEBI
Amantidine	ChEBI
Aminoadamantane	ChEBI
Tricyclo[3.3.1.1(3,7)]decan-1-amine	ChEBI
Tricyclo[3.3.1.1(3,7)]decan-1-ylamine	ChEBI
Tricyclo[3.3.1.1(3,7)]decane-1-amine	ChEBI
Viregyt	ChEBI
Virosol	ChEBI
Adamantamine	HMDB
Adamantanamine	HMDB
Adamantylamine	HMDB
Amantadine base	HMDB
Amantadine HCL	HMDB
Amantadine hydrochloride	HMDB
AL, amantadin	HMDB
Adekin	HMDB
Alliance brand OF amantadine hydrochloride	HMDB
Aman	HMDB
Amanta-sulfate-azu	HMDB
AmantaHCIAZU	HMDB
Amantadin al	HMDB
Amantadin neuraxpharm	HMDB
Amantadin ratiopharm	HMDB
Amantadin-neuraxpharm	HMDB
Amantadina juventus	HMDB
Amantadinratiopharm	HMDB
Desitin brand OF amantadine hydrochloride	HMDB
Infecto-flu	HMDB
Krewel brand OF amantadine hydrochloride	HMDB
Merz brand OF amantadine sulfate	HMDB
Novartis brand OF amantadine hydrochloride	HMDB
PMSAmantadine	HMDB
Solvay brand OF amantadine hydrochloride	HMDB
Stada brand OF amantadine hydrochloride	HMDB
Symmetrel	HMDB
Tregor	HMDB
AbZ brand OF amantadine hydrochloride	HMDB
Aliud brand OF amantadine sulfate	HMDB
Amanta-hci-azu	HMDB
Amantadina llorente	HMDB
Azupharma brand OF amantadine hydrochloride	HMDB
Azupharma brand OF amantadine sulfate	HMDB
Cerebramed	HMDB
Gen amantadine	HMDB
GenAmantadine	HMDB
Hexal brand OF amantadine sulfate	HMDB
Infecto flu	HMDB
Infectopharm brand OF amantadine hydrochloride	HMDB
Neuro hexal brand OF amantadine sulfate	HMDB
PMS-Amantadine	HMDB
Pharmascience brand OF amantadine hydrochloride	HMDB
Symadine	HMDB
Thiemann brand OF amantadine hydrochloride	HMDB
AZU, amantadin	HMDB
Amanta	HMDB
Amanta hci azu	HMDB
Amantadin stada	HMDB
Amantadin-ratiopharm	HMDB
Gen-amantadine	HMDB
Genpharm brand OF amantadine hydrochloride	HMDB
Hormosan brand OF amantadine sulfate	HMDB
Hydrochloride, amantadine	HMDB
Juventus, amantadina	HMDB
Mantadix	HMDB
Stada brand OF amantadine sulfate	HMDB
Stada, amantadin	HMDB
Sulfate, amantadine	HMDB
1 Aminoadamantane	HMDB
Amanta sulfate azu	HMDB
Amantasulfateazu	HMDB
Amantadin azu	HMDB
Amantadine sulfate	HMDB
Amantadinneuraxpharm	HMDB
Amixx	HMDB
Ciba geigy brand OF amantadine hydrochloride	HMDB
Ciba-geigy brand OF amantadine hydrochloride	HMDB
Du pont brand OF amantadine hydrochloride	HMDB
Endantadine	HMDB
endo Brand OF amantadine hydrochloride	HMDB
InfectoFlu	HMDB
Infex	HMDB
Juventus brand OF amantadine hydrochloride	HMDB
Llorente brand OF amantadine hydrochloride	HMDB
Llorente, amantadina	HMDB
Midantan	HMDB
Orion brand OF amantadine hydrochloride	HMDB
PMS Amantadine	HMDB
Wiregyt	HMDB
Neuraxpharm brand OF amantadine sulfate	HMDB
Ratiopharm brand OF amantadine hydrochloride	HMDB

Chemical Formula

C₁₀H₁₇N

Average Molecular Weight

151.2487

Monoisotopic Molecular Weight

151.136099549

IUPAC Name

adamantan-1-amine

Traditional Name

amantadine

CAS Registry Number

768-94-5

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 Key

DKNWSYNQZKUICI-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

adamantanes (CHEBI:2618 )
primary aliphatic amine (CHEBI:2618 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015051)

Process

Not Available

Role

Industrial application

Non-narcotic analgesic (HMDB: HMDB0015051)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Analgesic (HMDB: HMDB0015051)

Pharmaceutical industry

Antiviral drug (HMDB: HMDB0015051)
Antiparkinson drug (HMDB: HMDB0015051)

Biological role

NMDA receptor antagonist (HMDB: HMDB0015051)
Dopaminergic agent (HMDB: HMDB0015051)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	180 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.085 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	138.594	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000698

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.085 g/L	ALOGPS
logP	2.53	ALOGPS
logP	1.47	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	10.71	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.54 m³·mol⁻¹	ChemAxon
Polarizability	17.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.803	31661259
DarkChem	[M-H]-	127.701	31661259
DeepCCS	[M-2H]-	173.702	30932474
DeepCCS	[M+Na]+	148.804	30932474
AllCCS	[M+H]+	134.9	32859911
AllCCS	[M+H-H2O]+	130.5	32859911
AllCCS	[M+NH4]+	138.9	32859911
AllCCS	[M+Na]+	140.1	32859911
AllCCS	[M-H]-	136.3	32859911
AllCCS	[M+Na-2H]-	137.0	32859911
AllCCS	[M+HCOO]-	137.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.18 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4698 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.98 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	137.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1389.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	341.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	194.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	268.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	377.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	357.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	307.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	881.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	277.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	966.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	237.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	272.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	552.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	331.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	343.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amantadine	NC12CC3CC(CC(C3)C1)C2	1472.2	Standard polar	33892256
Amantadine	NC12CC3CC(CC(C3)C1)C2	1276.0	Standard non polar	33892256
Amantadine	NC12CC3CC(CC(C3)C1)C2	1227.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amantadine,1TMS,isomer #1	C[Si](C)(C)NC12CC3CC(CC(C3)C1)C2	1472.3	Semi standard non polar	33892256
Amantadine,1TMS,isomer #1	C[Si](C)(C)NC12CC3CC(CC(C3)C1)C2	1437.8	Standard non polar	33892256
Amantadine,1TMS,isomer #1	C[Si](C)(C)NC12CC3CC(CC(C3)C1)C2	1781.1	Standard polar	33892256
Amantadine,2TMS,isomer #1	C[Si](C)(C)N(C12CC3CC(CC(C3)C1)C2)[Si](C)(C)C	1651.2	Semi standard non polar	33892256
Amantadine,2TMS,isomer #1	C[Si](C)(C)N(C12CC3CC(CC(C3)C1)C2)[Si](C)(C)C	1688.4	Standard non polar	33892256
Amantadine,2TMS,isomer #1	C[Si](C)(C)N(C12CC3CC(CC(C3)C1)C2)[Si](C)(C)C	1913.6	Standard polar	33892256
Amantadine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC12CC3CC(CC(C3)C1)C2	1749.3	Semi standard non polar	33892256
Amantadine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC12CC3CC(CC(C3)C1)C2	1723.7	Standard non polar	33892256
Amantadine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC12CC3CC(CC(C3)C1)C2	1941.5	Standard polar	33892256
Amantadine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C12CC3CC(CC(C3)C1)C2)[Si](C)(C)C(C)(C)C	2138.3	Semi standard non polar	33892256
Amantadine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C12CC3CC(CC(C3)C1)C2)[Si](C)(C)C(C)(C)C	2173.4	Standard non polar	33892256
Amantadine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C12CC3CC(CC(C3)C1)C2)[Si](C)(C)C(C)(C)C	2104.2	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00915	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00915	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00915

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2045

KEGG Compound ID

C06818

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amantadine

METLIN ID

Not Available

PubChem Compound

2130

PDB ID

Not Available

ChEBI ID

2618

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

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

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 ]

Enzyme Details

2. Aromatic-L-amino-acid decarboxylase

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

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 ]
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 ]

Enzyme Details

3. D(2) dopamine receptor

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

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 ]
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 ]
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 ]
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 ]

Enzyme Details

4. Glutamate [NMDA] receptor subunit 3A

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

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 ]
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 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

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

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 ]

Enzyme Details

2. Solute carrier family 22 member 1

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

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 ]
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 ]
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 ]
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 ]

Enzyme Details

3. Solute carrier family 22 member 2

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

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 ]
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 ]
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 ]
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 ]

Showing metabocard for Amantadine (HMDB0015051)

MOL for HMDB0015051 (Amantadine)

3D MOL for HMDB0015051 (Amantadine)

3D SDF for HMDB0015051 (Amantadine)

3D-SDF for HMDB0015051 (Amantadine)

PDB for HMDB0015051 (Amantadine)

3D PDB for HMDB0015051 (Amantadine)

SMILES for HMDB0015051 (Amantadine)

INCHI for HMDB0015051 (Amantadine)

Structure for HMDB0015051 (Amantadine)

3D Structure for HMDB0015051 (Amantadine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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Transporters

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