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Details

Stereochemistry ACHIRAL
Molecular Formula C5H6N2
Molecular Weight 94.1145
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DALFAMPRIDINE

SMILES

NC1=CC=NC=C1

InChI

InChIKey=NUKYPUAOHBNCPY-UHFFFAOYSA-N
InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)

HIDE SMILES / InChI

Description

Dalfampridine is a potassium channel blocker, used as a research tool in characterizing subtypes of the potassium channel. Dalfampridine has also been used as a drug, to manage some of the symptoms of multiple sclerosis, and is indicated for symptomatic improvement of walking in adults with several variations of the disease. The mechanism by which dalfampridine exerts its therapeutic effect has not been fully elucidated. Dalfampridine is a broad spectrum potassium channel blocker. In animal studies, dalfampridine has been shown to increase conduction of action potentials in demyelinated axons through inhibition of potassium channels.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
195.0 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMPYRA
PubMed

PubMed

TitleDatePubMed
Treatment of the neuromuscular junction with 4-aminopyridine results in improved reinnervation following nerve injury in neonatal rats.
2001
The expression and regulation of depolarization-activated K+ channels in the insulin-secreting cell line INS-1.
2001 Apr
Differential expression of KV and KCa channels in vascular smooth muscle cells during 1-day culture.
2001 Apr
Inhibition of vesicular glutamate storage and exocytotic release by Rose Bengal.
2001 Apr
Okadaic acid and cyclosporin A modulate [(3)H]GABA release from rat brain synaptosomes.
2001 Apr
General rules for the packing of hydrogen-bonded crystals as derived from the analysis of squaric acid anions: aminoaromatic nitrogen base co-crystals.
2001 Aug
Resolving the gating charge movement associated with late transitions in K channel activation.
2001 Aug
A model for 4-aminopyridine action on K channels: similarities to tetraethylammonium ion action.
2001 Aug
Fenfluramine-induced pulmonary vasoconstriction: role of serotonin receptors and potassium channels.
2001 Aug
The relaxation induced by S-nitroso-glutathione and S-nitroso-N-acetylcysteine in rat aorta is not related to nitric oxide production.
2001 Aug
Chloride distribution in the CA1 region of newborn and adult hippocampus by light microscopic histochemistry.
2001 Feb
Large-conductance calcium-activated potassium channels in neonatal rat intracardiac ganglion neurons.
2001 Feb
Validation of a CE assay for the analysis of isomeric aminopyridines and diaminopyridines.
2001 Feb
Coordinated control of cell Ca(2+) loading and triggered release from the sarcoplasmic reticulum underlies the rapid inotropic response to increased L-type Ca(2+) current.
2001 Feb 2
The effect of acidosis on the ECG of the rat heart.
2001 Jan
Three types of K(+) currents in murine osteocyte-like cells (MLO-Y4).
2001 Jan
Phorbol ester-induced inhibition of potassium currents in rat sensory neurons requires voltage-dependent entry of calcium.
2001 Jan
Role of potassium channels in regulation of brain arteriolar tone: comparison of cerebrum versus brain stem.
2001 Jan
Neurogenic bladder in Lambert-Eaton myasthenic syndrome and its response to 3,4-diaminopyridine.
2001 Jan 15
Diversity of K+ channels in circular smooth muscle of opossum lower esophageal sphincter.
2001 Jul
Pharmacological evidence for the activation of potassium channels as the mechanism involved in the hypotensive and vasorelaxant effect of dioclein in rat small resistance arteries.
2001 Jul
Imaging of 4-AP-induced, GABA(A)-dependent spontaneous synchronized activity mediated by the hippocampal interneuron network.
2001 Jul
KT3.2 and KT3.3, two novel human two-pore K(+) channels closely related to TASK-1.
2001 Jul
Long-term recordings of networks of immortalized GnRH neurons reveal episodic patterns of electrical activity.
2001 Jul
Relaxation to authentic nitric oxide and SIN-1 in rat isolated mesenteric arteries: variable role for smooth muscle hyperpolarization.
2001 Jul
Bcl-2 decreases voltage-gated K+ channel activity and enhances survival in vascular smooth muscle cells.
2001 Jul
Gap junctions synchronize the firing of inhibitory interneurons in guinea pig hippocampus.
2001 Jul 13
High glucose impairs voltage-gated K(+) channel current in rat small coronary arteries.
2001 Jul 20
Lamotrigine inhibition of glutamate release from isolated cerebrocortical nerve terminals (synaptosomes) by suppression of voltage-activated calcium channel activity.
2001 Jul 20
A novel mechanical dissociation technique for studying acutely isolated maturing Drosophila central neurons.
2001 Jul 30
Role of K+ -channels in homotaurine-induced analgesia.
2001 Jun
Normal coordinate analysis of 4-aminopyridine. Effect of substituent on pyridine ring in metal complexes of 4-substituted pyridines.
2001 Jun
Focal cooling rapidly terminates experimental neocortical seizures.
2001 Jun
Tonotopic map of potassium currents in chick auditory hair cells using an intact basilar papilla.
2001 Jun
Superfusion of synaptosomes to study presynaptic mechanisms involved in neurotransmitter release from rat brain.
2001 Jun
Mechanisms underlying presynaptic facilitatory effect of cyclothiazide at the calyx of Held of juvenile rats.
2001 Jun 1
Theoretical analysis of the molecular determinants responsible for the K(+) channel blocking by aminopyridines.
2001 Jun 15
"Use-dependent" effects of cisapride on postrest action potentials in rabbit ventricular myocardium.
2001 Jun 22
Developmental characteristics of epileptiform activity in immature rat neocortex: a comparison of four in vitro seizure models.
2001 Jun 29
Modulation of voltage-dependent K+ channel current in vascular smooth muscle cells from rat mesenteric arteries.
2001 Mar 15
Capsaicin-induced relaxation in rabbit coronary artery.
2001 May
Sites and ionic mechanisms of hypoxic vasoconstriction in frog skin.
2001 May
Ion channels associated with the ectopic discharges generated after segmental spinal nerve injury in the rat.
2001 May 4
BTS 72664-- a novel CNS drug with potential anticonvulsant, neuroprotective, and antimigraine properties.
2001 Summer
Patents

Sample Use Guides

In Vivo Use Guide
The maximum recommended dose of AMPYRA is one 10 mg tablet twice daily, taken with or without food, and should not be exceeded.
Route of Administration: Oral
In Vitro Use Guide
At DIV25, the differentiating cells were re-seeded to Matrigel coated 12-mm glass coverslips in densities of 400,000 cells per well. Media was replaced completely the next day by fresh maturation media. Media containing either 100 mM 4-Aminopyridine diluted in DMSO or the equivalent amount DMSO only was given to the cells 72 hours before the start of week 7 (DIV42) and lasted until the cells were analyzed during week 7. Half the media was replaced every third day. Final electrophysiological recordings of the treated vs. non-treated cells rigorously were taken in pairs of one treated and one nontreated coverslip within a time frame of 48 hours.
Name Type Language
DALFAMPRIDINE
DASH   HSDB   II   MI   ORANGE BOOK   USAN   USP-RS   VANDF  
USAN  
Official Name English
FAMPRIDINE [INN]
Common Name English
DALFAMPRIDINE [HSDB]
Common Name English
FAMPRIDINE
EMA EPAR   INN   MART.   VANDF   WHO-DD  
INN  
Official Name English
DALFAMPRIDINE [II]
Common Name English
DALFAMPRIDINE [MI]
Common Name English
4-AP
Common Name English
FAMPRIDINE [MART.]
Common Name English
DALFAMPRIDINE [ORANGE BOOK]
Common Name English
AMPYRA
Brand Name English
DALFAMPRIDINE [USAN]
Common Name English
FAMPRIDINE [WHO-DD]
Common Name English
DALFAMPRIDINE [VANDF]
Common Name English
PYRIDIN-4-AMINE
Systematic Name English
FAMPRIDINE (4-AMINOPYRIDINE) [VANDF]
Common Name English
DALFAMPRIDINE [USP-RS]
Common Name English
4-PYRIDINAMINE
Systematic Name English
FAMPRIDINE [VANDF]
Common Name English
FAMPRIDINE [EMA EPAR]
Common Name English
4-AMINOPYRIDINE
Systematic Name English
EL-970
Code English
NSC-15041
Code English
FAMPYRA
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C93038
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
FDA ORPHAN DRUG 18186
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
FDA ORPHAN DRUG 214205
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
FDA ORPHAN DRUG 104497
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
EMA ASSESSMENT REPORTS FAMPYRA (AUTHORIZED: MULTIPLE SCLEROSIS)
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
EU-Orphan Drug EU/3/07/458
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
NDF-RT N0000192795
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
LIVERTOX 259
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
WHO-ATC N07XX07
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
WHO-VATC QN07XX07
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
EPA PESTICIDE CODE 69201
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
Code System Code Type Description
INN
7283
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
PUBCHEM
1727
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
MERCK INDEX
M4072
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY Merck Index
HSDB
504-24-5
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
IUPHAR
2416
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
NCI_THESAURUS
C76777
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
EPA CompTox
504-24-5
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
CAS
504-24-5
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
ECHA (EC/EINECS)
207-987-9
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
MESH
D015761
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
EVMPD
SUB07505MIG
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
DRUG BANK
DB06637
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
WIKIPEDIA
4-AMINOPYRIDINE
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
ChEMBL
CHEMBL284348
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY
RXCUI
897018
Created by admin on Mon Oct 21 20:45:50 UTC 2019 , Edited by admin on Mon Oct 21 20:45:50 UTC 2019
PRIMARY RxNorm