fampridine   Click here for help

GtoPdb Ligand ID: 2416

Synonyms: 4-aminopyridine | 4-AP | Ampyra® | EL-970
Approved drug
fampridine is an approved drug (FDA (2010), EMA (2011))
Compound class: Synthetic organic
Comment: Fampridine is the INN for this compound, whereas its USAN is dalfampridine.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

fampridine is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 38.91
Molecular weight 94.05
XLogP -0.05
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES Nc1ccncc1
Isomeric SMILES Nc1ccncc1
InChI InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)
InChI Key NUKYPUAOHBNCPY-UHFFFAOYSA-N
Bioactivity Comments
This drug is non-selective in action and blocks many of the voltage-gated potassium channels. Where we have affinity data for human channels we have tagged these as the primary drug target.
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kir7.1 Hs Channel blocker Antagonist - - 1x10-3 - 1x10-2 11
⤷ Conc range: 1x10-3 - 1x10-2 M [11]
Voltage: -100.0 mV
TRPV2 Mm Channel blocker Inhibition - - 5x10-3 7
⤷ Conc range: 5x10-3 M [7]
Kv1.7 Mm Channel blocker Pore blocker 3.8 pKd - 2
⤷ pKd 3.8 [2]
Kv1.5 Hs Channel blocker Pore blocker 3.6 pKd - 4
⤷ pKd 3.6 (Kd 2.7x10-4 M) [4]
Kv1.2 Rn Channel blocker Pore blocker 3.2 pKd - 4
⤷ pKd 3.2 (Kd 5.9x10-4 M) [4]
Kv3.2 Rn Channel blocker - 4.6 pIC50 - 13
⤷ pIC50 4.6 (IC50 2.4x10-5 M) [13]
Kv3.1 Mm Channel blocker - 4.5 pIC50 - 4
⤷ pIC50 4.5 (IC50 2.9x10-5 M) [4]
Kv1.5 N/A Channel blocker - 4.3 pIC50 - 1
⤷ pIC50 4.3 [1]
Kv1.7 Mm Channel blocker - 3.6 pIC50 - 8
⤷ pIC50 3.6 (IC50 2.45x10-4 M) [8]
Kv2.1 Rn Channel blocker Pore blocker 3.3 pIC50 - 9
⤷ pIC50 3.3 (IC50 5x10-4 M) [9]
Kv3.3 Rn Channel blocker - 2.9 pIC50 - 17
⤷ pIC50 2.9 [17]
Kv1.8 Primary target of this compound Hs Channel blocker - 2.8 pIC50 - 12
⤷ pIC50 2.8 (IC50 1.58x10-3 M) [12]
Kv2.2 Primary target of this compound Hs Channel blocker - 2.8 pIC50 - 14
⤷ pIC50 2.8 (IC50 1.5x10-3 M) [14]
Kv4.3 Mm Channel blocker - 2.4 pIC50 - 18
⤷ pIC50 2.4 [18]
Kv4.2 Mm Channel blocker - 2.3 pIC50 - 3
⤷ pIC50 2.3 [3]
Kv4.1 Primary target of this compound Hs Channel blocker - 2.0 pIC50 - 6
⤷ pIC50 2.0 [6]
Kv4.1 Mm Channel blocker - 2.0 pIC50 - 5
⤷ pIC50 2.0 [5]
Kv1.4 Rn Channel blocker - 1.9 pIC50 - 16
⤷ pIC50 1.9 (IC50 1.25x10-2 M) [16]
Ligand mentioned in the following text fields
Two-pore domain potassium channels (K2P) comments