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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL660
CHEMBL660
Compound Name AMANTADINE
ChEMBL Synonyms MANTADINE | ADAMANTANAMINE HYDROCHLORIDE | Amantadine Sulfate | Symmetrel | GOCOVRI | AMANTADINE HYDROCHLORIDE | LYSOVIR | Symadine | AMANTADINE | EXP-105-1 | SYMMETREL | SYMADINE
Max Phase 4 (Approved)
Trade Names SYMMETREL | AMANTADINE HYDROCHLORIDE | GOCOVRI | LYSOVIR | SYMADINE | MANTADINE
Molecular Formula C10H17N

Additional synonyms for CHEMBL660 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NC12CC3CC(CC(C3)C1)C2
Standard InChI InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6, ...
Download InChI
Standard InChI Key DKNWSYNQZKUICI-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • GSK Malaria Screening
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • St Jude Leishmania Screening
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL660

Molecule Features

CHEMBL660 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Glutamate [NMDA] receptor antagonist Glutamate [NMDA] receptor DailyMed
Matrix protein 2 inhibitor Matrix protein 2 DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Parkinson DiseaseD010300EFO:0002508Parkinson's disease4ATC
ClinicalTrials
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Wounds and InjuriesD014947EFO:0000546injury2ClinicalTrials
Hepatitis CD006526EFO:0003047hepatitis C infection2ClinicalTrials
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Hepatitis C, ChronicD019698EFO:0004220Chronic Hepatitis C infection3ClinicalTrials
Mood DisordersD019964EFO:0004247mood disorder1ClinicalTrials
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Cocaine-Related DisordersD019970EFO:0002610cocaine dependence2ClinicalTrials
Intracranial ArteriosclerosisD002537EFO:1000860cerebral atherosclerosis4DailyMed
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Brain InfarctionD020520EFO:0004277brain infarction2ClinicalTrials
Parkinson Disease, SecondaryD010302EFO:1001175secondary Parkinson disease4DailyMed
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Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus2ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
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Multiple SclerosisD009103EFO:0003885multiple sclerosis3ClinicalTrials
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Attention Deficit Disorder with HyperactivityD001289EFO:0003888attention deficit hyperactivity disorder2ClinicalTrials
Influenza, HumanD007251EFO:0001669influenza infection4DailyMed
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ClinicalTrials
InfectionD007239EFO:0000544infection4DailyMed
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FDA
ClinicalTrials
Psychotic DisordersD011618EFO:0005411schizoaffective disorder3ClinicalTrials
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Parkinson Disease, PostencephaliticD010301EFO:1001402postencephalitic Parkinson disease4DailyMed
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Clinical Data

ClinicalTrials.gov AMANTADINE
The Cochrane Collaboration AMANTADINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL660. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL3638334 Opioid growth factor receptor-like protein 1 Homo sapiens 1.000
CHEMBL4235 11-beta-hydroxysteroid dehydrogenase 1 Homo sapiens 1.000
CHEMBL2409 Epoxide hydratase Homo sapiens 1.000
CHEMBL3910 11-beta-hydroxysteroid dehydrogenase 1 Mus musculus 1.000
CHEMBL2888 Metabotropic glutamate receptor 3 Homo sapiens 0.996
CHEMBL2391 11-beta-hydroxysteroid dehydrogenase 1 Rattus norvegicus 0.996
CHEMBL4140 Epoxide hydratase Mus musculus 0.988
CHEMBL1968 Epoxide hydrolase 1 Homo sapiens 0.958
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 0.716
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 0.641
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 0.550
CHEMBL3419 Carboxypeptidase B2 isoform A Homo sapiens 0.429
CHEMBL237 Kappa opioid receptor Homo sapiens 0.427
CHEMBL304 Norepinephrine transporter Rattus norvegicus 0.417
CHEMBL233 Mu opioid receptor Homo sapiens 0.363
CHEMBL3746 11-beta-hydroxysteroid dehydrogenase 2 Homo sapiens 0.342
CHEMBL2470 Cannabinoid CB2 receptor Rattus norvegicus 0.341



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3638334 Opioid growth factor receptor-like protein 1 Homo sapiens 1.000
CHEMBL4235 11-beta-hydroxysteroid dehydrogenase 1 Homo sapiens 1.000
CHEMBL3910 11-beta-hydroxysteroid dehydrogenase 1 Mus musculus 1.000
CHEMBL2409 Epoxide hydratase Homo sapiens 1.000
CHEMBL2391 11-beta-hydroxysteroid dehydrogenase 1 Rattus norvegicus 0.997
CHEMBL2888 Metabotropic glutamate receptor 3 Homo sapiens 0.995
CHEMBL4140 Epoxide hydratase Mus musculus 0.982
CHEMBL1968 Epoxide hydrolase 1 Homo sapiens 0.973
CHEMBL3746 11-beta-hydroxysteroid dehydrogenase 2 Homo sapiens 0.906
CHEMBL4573 Metabotropic glutamate receptor 6 Homo sapiens 0.901
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 0.816
CHEMBL3419 Carboxypeptidase B2 isoform A Homo sapiens 0.726
CHEMBL233 Mu opioid receptor Homo sapiens 0.722
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 0.715
CHEMBL237 Kappa opioid receptor Homo sapiens 0.639
CHEMBL304 Norepinephrine transporter Rattus norvegicus 0.502
CHEMBL2748 Sucrase-isomaltase Homo sapiens 0.355
CHEMBL218 Cannabinoid CB1 receptor Homo sapiens 0.329
CHEMBL338 Dopamine transporter Rattus norvegicus 0.326
CHEMBL2470 Cannabinoid CB2 receptor Rattus norvegicus 0.294

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
151.3 151.1361 1.91 0 26.02 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
1 1 0 1 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 10.76 2.44 -.47 0 11 0.56

Structural Alerts

There are 1 structural alerts for CHEMBL660. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N04 - ANTI-PARKINSON DRUGS
N04B - DOPAMINERGIC AGENTS
N04BB - Adamantane derivatives
N04BB01 - amantadine

ChemSpider ChemSpider:DKNWSYNQZKUICI-UHFFFAOYSA-N
DailyMed amantadine hydrochloride
PubChem SID: 104171100 SID: 11110715 SID: 124879107 SID: 144203619 SID: 170464860 SID: 26755640 SID: 26755641 SID: 50110918 SID: 50110919 SID: 90340894
Wikipedia Amantadine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL660



ACToR 768-94-5
BindingDB 50033369
Brenda 16839 200826
ChEBI 2618
ChemicalBook CB3259991
DrugBank DB00915
DrugCentral 144
eMolecules 27515804 476391
EPA CompTox Dashboard DTXSID8022117
FDA SRS BF4C9Z1J53
Guide to Pharmacology 4128
Human Metabolome Database HMDB0015051
IBM Patent System EC206C62E6C79CD111C5F3D8BB20ED9B
KEGG Ligand C06818
LINCS LSM-3571
Mcule MCULE-9686682307
MolPort MolPort-001-661-700
NMRShiftDB 10006057
PharmGKB PA448360
PubChem 2130
PubChem: Thomson Pharma 15219251
SureChEMBL SCHEMBL4098
ZINC ZINC000000968256

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/DKNWSYNQZKUICI-UHFFFAOYSA-N spacer
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