Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H6N2 |
Molecular Weight | 94.1145 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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)
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugs.com/cdi/dalfampridine.html | https://clinicaltrials.gov/ct2/show/NCT01356940 | https://www.ncbi.nlm.nih.gov/pubmed/22497693 | https://www.ncbi.nlm.nih.gov/pubmed/15084131
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/cdi/dalfampridine.html | https://clinicaltrials.gov/ct2/show/NCT01356940 | https://www.ncbi.nlm.nih.gov/pubmed/22497693 | https://www.ncbi.nlm.nih.gov/pubmed/15084131
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4633 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15084131 |
195.0 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AMPYRA Approved UseAMPYRA (dalfampridine) is indicated as a treatment to improve walking in patients with multiple sclerosis (MS). This was demonstrated by an increase in walking speed [see Clinical Studies (14) Launch Date1.2641184E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23.77 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22058101/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
DALFAMPRIDINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
246.48 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22058101/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
DALFAMPRIDINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.16 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22058101/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
DALFAMPRIDINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
97% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22058101/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
DALFAMPRIDINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: Page: p.3 |
unhealthy, 52.1 ± 8.8 n = 269 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 52.1 ± 8.8 Sex: M+F Population Size: 269 Sources: Page: p.3 |
Disc. AE: Seizure, Myocardial infarction... AEs leading to discontinuation/dose reduction: Seizure (1.1%) Sources: Page: p.3Myocardial infarction (1.1%) |
300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 1 Sources: Page: p.3 |
Disc. AE: Weakness, Consciousness decreased... AEs leading to discontinuation/dose reduction: Weakness Sources: Page: p.3Consciousness decreased Memory loss Hypophonia Structural brain disorders NEC |
40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Sex: F Population Size: 1 Sources: Page: p.3 |
Disc. AE: Complex partial seizures, Confusion... AEs leading to discontinuation/dose reduction: Complex partial seizures Sources: Page: p.3Confusion |
60 mg single, oral Overdose Dose: 60 mg Route: oral Route: single Dose: 60 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 1 Sources: Page: p.3 |
Disc. AE: Mental state abnormal... AEs leading to discontinuation/dose reduction: Mental state abnormal Sources: Page: p.3 |
10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: Page: p.2 |
unhealthy n = 400 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 400 Sources: Page: p.2 |
Disc. AE: Headache, Balance disorder... AEs leading to discontinuation/dose reduction: Headache (0.5%) Sources: Page: p.2Balance disorder (0.5%) Dizziness (0.5%) Confusional state (0.5%) |
10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Multiple sclerosis Sources: Page: p.1 |
Disc. AE: Seizures... AEs leading to discontinuation/dose reduction: Seizures Sources: Page: p.1 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Myocardial infarction | 1.1% Disc. AE |
10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: Page: p.3 |
unhealthy, 52.1 ± 8.8 n = 269 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 52.1 ± 8.8 Sex: M+F Population Size: 269 Sources: Page: p.3 |
Seizure | 1.1% Disc. AE |
10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: Page: p.3 |
unhealthy, 52.1 ± 8.8 n = 269 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 52.1 ± 8.8 Sex: M+F Population Size: 269 Sources: Page: p.3 |
Consciousness decreased | Disc. AE | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 1 Sources: Page: p.3 |
Hypophonia | Disc. AE | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 1 Sources: Page: p.3 |
Memory loss | Disc. AE | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 1 Sources: Page: p.3 |
Structural brain disorders NEC | Disc. AE | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 1 Sources: Page: p.3 |
Weakness | Disc. AE | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 1 Sources: Page: p.3 |
Complex partial seizures | Disc. AE | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Sex: F Population Size: 1 Sources: Page: p.3 |
Confusion | Disc. AE | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Sex: F Population Size: 1 Sources: Page: p.3 |
Mental state abnormal | Disc. AE | 60 mg single, oral Overdose Dose: 60 mg Route: oral Route: single Dose: 60 mg Sources: Page: p.3 |
unhealthy n = 1 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 1 Sources: Page: p.3 |
Balance disorder | 0.5% Disc. AE |
10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: Page: p.2 |
unhealthy n = 400 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 400 Sources: Page: p.2 |
Confusional state | 0.5% Disc. AE |
10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: Page: p.2 |
unhealthy n = 400 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 400 Sources: Page: p.2 |
Dizziness | 0.5% Disc. AE |
10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: Page: p.2 |
unhealthy n = 400 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 400 Sources: Page: p.2 |
Headache | 0.5% Disc. AE |
10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: Page: p.2 |
unhealthy n = 400 Health Status: unhealthy Condition: Multiple sclerosis Population Size: 400 Sources: Page: p.2 |
Seizures | Disc. AE | 10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Multiple sclerosis Sources: Page: p.1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
Page: 41, (ClinPharm) 28, 50 |
no | |||
Page: 41, (ClinPharm) 28, 50 |
no | |||
no | ||||
Page: 41, (ClinPharm) 28, 50 |
no | |||
no | ||||
Page: 41, (ClinPharm) 28, 50 |
no | |||
Page: 41, (ClinPharm) 28, 50 |
no | |||
no | ||||
Page: 41, (ClinPharm) 28, 50 |
no | |||
Page: 41, (ClinPharm) 28, 50 |
no | |||
no | ||||
no | ||||
Page: 41, (ClinPharm) 28, 50 |
no | |||
no | ||||
Page: 32; Pharmacological Reviews December 2005, 57 (4) 473-508 |
weak [IC50 195 uM] | |||
Page: 33; Pharmacological Reviews December 2005, 57 (4) 473-508 |
weak [IC50 270 uM] |
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Gene structures and expression profiles of three human KCND (Kv4) potassium channels mediating A-type currents I(TO) and I(SA). | 2000 Mar 1 |
|
Treatment of the neuromuscular junction with 4-aminopyridine results in improved reinnervation following nerve injury in neonatal rats. | 2001 |
|
Firing properties of identified superior laryngeal neurons in the nucleus ambiguus in the rat. | 2001 Apr 27 |
|
Effects of phosphodiesterase inhibitors on hypoxic pulmonary vasoconstriction. Influence of K(+) channels and nitric oxide. | 2001 Apr 6 |
|
A model for 4-aminopyridine action on K channels: similarities to tetraethylammonium ion action. | 2001 Aug |
|
Blockage of one class of potassium channel alters the effectiveness of halothane in a brain circuit of Drosophila. | 2001 Feb |
|
Theta-frequency bursting and resonance in cerebellar granule cells: experimental evidence and modeling of a slow k+-dependent mechanism. | 2001 Feb 1 |
|
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 |
|
Activation of potassium conductance by ophiopogonin-D in acutely dissociated rat paratracheal neurones. | 2001 Jan |
|
Phorbol ester-induced inhibition of potassium currents in rat sensory neurons requires voltage-dependent entry of calcium. | 2001 Jan |
|
Development and validation of a capillary electrophoresis assay for the determination of 3,4-diaminopyridine and 4-aminopyridine including related substances. | 2001 Jan 12 |
|
K(ATP) channel blockers selectively interact with A(1)-adenosine receptor mediated modulation of acetylcholine release in the rat hippocampus. | 2001 Jan 19 |
|
Diversity of K+ channels in circular smooth muscle of opossum lower esophageal sphincter. | 2001 Jul |
|
KT3.2 and KT3.3, two novel human two-pore K(+) channels closely related to TASK-1. | 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 |
|
Role of K+ -channels in homotaurine-induced analgesia. | 2001 Jun |
|
Potassium channels regulate tone in rat pulmonary veins. | 2001 Jun |
|
Mechanisms underlying presynaptic facilitatory effect of cyclothiazide at the calyx of Held of juvenile rats. | 2001 Jun 1 |
|
Membrane resonance and subthreshold membrane oscillations in mesencephalic V neurons: participants in burst generation. | 2001 Jun 1 |
|
Theoretical analysis of the molecular determinants responsible for the K(+) channel blocking by aminopyridines. | 2001 Jun 15 |
|
Potassium channel blocker TEA prevents CA1 hippocampal injury following transient forebrain ischemia in adult rats. | 2001 Jun 8 |
|
Effects of pituitary adenylate cyclase activating polypeptide on lumbosacral preganglionic neurons in the neonatal rat spinal cord. | 2001 Mar 23 |
|
Sites and ionic mechanisms of hypoxic vasoconstriction in frog skin. | 2001 May |
|
Mobilization of calcium from intracellular stores, potentiation of neurotransmitter-induced calcium transients, and capacitative calcium entry by 4-aminopyridine. | 2001 May 1 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26946488
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C93038
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FDA ORPHAN DRUG |
18186
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FDA ORPHAN DRUG |
214205
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FDA ORPHAN DRUG |
104497
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EMA ASSESSMENT REPORTS |
FAMPYRA (AUTHORIZED: MULTIPLE SCLEROSIS)
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EU-Orphan Drug |
EU/3/07/458
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NDF-RT |
N0000192795
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FDA ORPHAN DRUG |
713019
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LIVERTOX |
NBK548455
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WHO-ATC |
N07XX07
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WHO-VATC |
QN07XX07
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EPA PESTICIDE CODE |
69201
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1162454
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7283
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1727
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BH3B64OKL9
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m4072
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PRIMARY | Merck Index | ||
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6037
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4-aminopyridine
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2416
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100000081574
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4163
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C76777
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FF-74
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DTXSID0023870
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15041
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Dalfampridine
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504-24-5
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207-987-9
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D015761
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BH3B64OKL9
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SUB07505MIG
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34385
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DB06637
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4-AMINOPYRIDINE
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CHEMBL284348
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897018
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PRIMARY | RxNorm |
ACTIVE MOIETY
METABOLITE INACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
SALT/SOLVATE (PARENT)