amantadine   Click here for help

GtoPdb Ligand ID: 4128

Synonyms: ADS-5102 | Gocovri® | Symadine® | Symmetrel®
Approved drug
amantadine is an approved drug (FDA (1966))
Compound class: Synthetic organic
Comment: Chemically amantadine has an adamantane backbone with an amino group substituted at one of the four methyne positions. Clinically it has antiviral (blocking the viral M2 proton channel) and antiparkinsonian actions.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 26.02
Molecular weight 151.14
XLogP 2.31
No. Lipinski's rules broken 0
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Canonical SMILES NC12CC3CC(C2)CC(C1)C3
Isomeric SMILES NC12CC3CC(C2)CC(C1)C3
InChI InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2
1. Dravid SM, Erreger K, Yuan H, Nicholson K, Le P, Lyuboslavsky P, Almonte A, Murray E, Mosely C, Barber J et al.. (2007)
Subunit-specific mechanisms and proton sensitivity of NMDA receptor channel block.
J Physiol (Lond.), 581 (Pt 1): 107-28. [PMID:17303642]
2. Oertel W, Eggert K, Pahwa R, Tanner CM, Hauser RA, Trenkwalder C, Ehret R, Azulay JP, Isaacson S, Felt L et al.. (2017)
Randomized, placebo-controlled trial of ADS-5102 (amantadine) extended-release capsules for levodopa-induced dyskinesia in Parkinson's disease (EASE LID 3).
Mov Disord, 32 (12): 1701-1709. [PMID:28833562]