AMANTADINE HYDROCHLORIDE

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Trade Names
Synonyms
Status
Molecule Category Salt-form
UNII M6Q1EO9TD0
EPA CompTox DTXSID50874031
Parent Compound: AMANTADINE

Structure

InChI Key WOLHOYHSEKDWQH-UHFFFAOYSA-N
Smiles Cl.NC12CC3CC(CC(C3)C1)C2
InChI
InChI=1S/C10H17N.ClH/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;/h7-9H,1-6,11H2;1H

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H18ClN
Molecular Weight 187.71
AlogP 1.91
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 26.02
Molecular species BASE
Aromatic Rings 0.0
Heavy Atoms 11.0

Bioactivity

Mechanism of Action Action Reference
Glutamate [NMDA] receptor antagonist ANTAGONIST DailyMed Wikipedia
Protein: Glutamate [NMDA] receptor
Description: Glutamate receptor ionotropic, NMDA 2D
Organism : Homo sapiens
O15399 ENSG00000105464
Protein: Glutamate [NMDA] receptor
Description: Glutamate receptor ionotropic, NMDA 3B
Organism : Homo sapiens
O60391 ENSG00000116032
Protein: Glutamate [NMDA] receptor
Description: Glutamate receptor ionotropic, NMDA 1
Organism : Homo sapiens
Q05586 ENSG00000176884
Protein: Glutamate [NMDA] receptor
Description: Glutamate receptor ionotropic, NMDA 2A
Organism : Homo sapiens
Q12879 ENSG00000183454
Protein: Glutamate [NMDA] receptor
Description: Glutamate receptor ionotropic, NMDA 2B
Organism : Homo sapiens
Q13224 ENSG00000273079
Protein: Glutamate [NMDA] receptor
Description: Glutamate receptor ionotropic, NMDA 2C
Organism : Homo sapiens
Q14957 ENSG00000161509
Protein: Glutamate [NMDA] receptor
Description: Glutamate receptor ionotropic, NMDA 3A
Organism : Homo sapiens
Q8TCU5 ENSG00000198785
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Ligand-gated ion channel Ionotropic glutamate receptor NMDA receptor
- 75000 - - -
Ion channel Other ion channel Miscellaneous ion channel Type A influenza virus matrix-2 channel family
- - - - 0-35
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 61
Assay Description Organism Bioactivity Reference
Binding affinity to influenza A virus A/chicken/Germany/27 H7N7 weybridge strain M2 ion channel expressed in Escherichia coli Influenza A virus 320.0 nM
Antiviral activity against influenza A virus H3N2 X31(A/Hong kong/1/68 x A/Puerto Rico/8/34 reassortant ) in MDCK cells assessed as reduction of virus-induced cytopathogenicity Influenza A virus 900.0 nM
Inhibition of Influenza A Virus M2 proton channel expressed in Xenopus laevis oocytes at 100 uM after 2 mins by two-electrode patch clamp assay Influenza A virus 91.0 %
Inhibition of Influenza A Virus M2 proton channel V27A mutant expressed in Xenopus laevis oocytes at 100 uM after 2 mins by two-electrode patch clamp assay Influenza A virus 0.0 %
Inhibition of Influenza A Virus M2 proton channel S31N mutant expressed in Xenopus laevis oocytes at 100 uM after 2 mins by two-electrode patch clamp assay Influenza A virus 35.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 60.52 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 88.29 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 17.85 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -0.07 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 13.94 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 10.58 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 16.01 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.06 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -3.67 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 6.78 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.99 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.54 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.54 %

Cross References

Resources Reference
ChEBI 2619
ChEMBL CHEMBL1569
FDA SRS M6Q1EO9TD0
Guide to Pharmacology 4128
KEGG C07939
PDB 308
PubChem 64150
SureChEMBL SCHEMBL40713
ZINC ZINC00968256
CONTENTS