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Compound Detail

CHEMBL1569

AMANTADINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
Cl.NC12CC3CC(CC(C3)C1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1569
Name AMANTADINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key WOLHOYHSEKDWQH-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL660
Active Moiety CHEMBL660

Known Names

Adamantanamine hydrochloride Amantadine hcl Amantadine hydrochloride EXP-105-1 Gocovri Lysovir Mantadine Mantadix NSC-83653 Osmolex Osmolex er Symadine +1 more
5
Targets
9
Activities
3
Assay Types
0
PK Parameters
20
Publications
13
Known Names
17
Indications
2
Mechanisms

Molecular Properties

151.2
MW (Da)
1.91
ALogP
1
HBA
1
HBD
26.0
PSA (Ų)
0.56
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1968
Availability Prescription
Chirality Achiral

Routes of Administration

Oral
USAN Stem -mantadine
USAN Year 1964

Extended Properties

Molecular Formula C10H18ClN
MW 187.71
Aromatic Rings 0
Heavy Atoms 11
NP-Likeness 0.55

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Glutamate [NMDA] receptor antagonist ANTAGONIST Glutamate [NMDA] receptor ✓ ✓
Matrix protein 2 inhibitor INHIBITOR Matrix protein 2 ✓ ✓

Indications

Infections Influenza, Human Intracranial Arteriosclerosis Parkinson Disease Parkinson Disease, Postencephalitic Parkinson Disease, Secondary Parkinsonian Disorders Multiple Sclerosis Severe Acute Respiratory Syndrome Amyotrophic Lateral Sclerosis Brain Injuries Hepatitis C Neoplasms Mental Disorders Mood Disorders Psychotic Disorders Schizophrenia

Activity Summary

IC50 6 meas. best 5.3
EC50 2 meas. best 5.96
Kd 1 meas. best 6.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 6.5 6.5 320.0 1
H2N2 subtype
CHEMBL612765
 EC50 5.96 5.96 1100.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.3 5.15 5011.9 2
Unchecked
CHEMBL612545
 IC50 4.8 4.8 16000.0 1
Influenza A virus
CHEMBL613740
 EC50 4.31 4.31 49100.0 1
Glutamate NMDA receptor
CHEMBL1907608
 IC50 4.12 4.12 75000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 320.0 nM 6.5 Binding affinity to influenza A virus A/chicken/Germany/27 H7N7 weybridge strain... 18947998
H2N2 subtype EC50 = 1100.0 nM 5.96 Antiviral activity against influenza A virus A/Japan/305/57 H2N2 in MDCK cells a... 18947998
Plasmodium falciparum IC50 = 5011.87 nM 5.3 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Unchecked IC50 = 16000.0 nM 4.8 Inhibition of Influenza A Virus M2 proton channel expressed in Xenopus laevis oo... 21691418
Influenza A virus EC50 = 49100.0 nM 4.31 Antiviral activity against influenza A virus (H3N2)-induced cytopathogenicity in... 17113287
Glutamate NMDA receptor IC50 = 75000.0 nM 4.12 Inhibition of NMDA receptor in rat cerebellar granule neurons assessed as NMDA-i... 18947998

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
18281929 10.1021/jm7014292 Trypanosoma brucei 2
18947998 10.1016/j.bmcl.2008.10.003 Glutamate NMDA receptor 2
21691418 10.1021/ml100297w Matrix protein 2 2
21691418 10.1021/ml100297w Unchecked 2
7473574 10.1021/jm00022a012 MDCK 2
19734910 10.1038/nchembio.215 Plasmodium falciparum 2
18947998 10.1016/j.bmcl.2008.10.003 MDCK 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1
20553011 10.1021/tx1000865 Hepatotoxicity 1
17417631 10.1038/nchembio873 Unchecked 1
18947998 10.1016/j.bmcl.2008.10.003 Influenza B virus 1
18947998 10.1016/j.bmcl.2008.10.003 Influenza A virus 1
18947998 10.1016/j.bmcl.2008.10.003 H2N2 subtype 1
18947998 10.1016/j.bmcl.2008.10.003 Unchecked 1
17113287 10.1016/j.bmcl.2006.10.092 MDCK 1
17113287 10.1016/j.bmcl.2006.10.092 Influenza A virus 1

Data from ChEMBL 36 via Core Engine