amifampridine   Click here for help

GtoPdb Ligand ID: 8032

Synonyms: 3,4-DAP | 3,4-diaminopyridine | Firdapse® | Ruzurgi® | Zenas®
Approved drug PDB Ligand
amifampridine is an approved drug (EMA (2009), FDA (2018))
Compound class: Synthetic organic
Comment: Amifampridine is a potassium channel blocker.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 64.93
Molecular weight 109.06
XLogP -0.86
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES Nc1cnccc1N
Isomeric SMILES Nc1cnccc1N
InChI InChI=1S/C5H7N3/c6-4-1-2-8-3-5(4)7/h1-3H,7H2,(H2,6,8)
InChI Key OYTKINVCDFNREN-UHFFFAOYSA-N
References
1. Rees JH. (2004)
Paraneoplastic syndromes: when to suspect, how to confirm, and how to manage.
J Neurol Neurosurg Psychiatr, 75 Suppl 2: ii43-50. [PMID:15146039]
2. Takamori M. (2008)
Lambert-Eaton myasthenic syndrome: search for alternative autoimmune targets and possible compensatory mechanisms based on presynaptic calcium homeostasis.
J Neuroimmunol, 201-202: 145-52. [PMID:18653248]
3. Tarr TB, Lacomis D, Reddel SW, Liang M, Valdomir G, Frasso M, Wipf P, Meriney SD. (2014)
Complete reversal of Lambert-Eaton myasthenic syndrome synaptic impairment by the combined use of a K+ channel blocker and a Ca2+ channel agonist.
J Physiol (Lond.), 592 (Pt 16): 3687-96. [PMID:25015919]
4. Verschuuren JJ, Wirtz PW, Titulaer MJ, Willems LN, van Gerven J. (2006)
Available treatment options for the management of Lambert-Eaton myasthenic syndrome.
Expert Opin Pharmacother, 7 (10): 1323-36. [PMID:16805718]