U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C5H6N2
Molecular Weight 94.1147
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DALFAMPRIDINE

SMILES

c1c[nH]ccc1=N

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
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.

Originator

Sources: Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (1915), 47, 835-8.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
195.0 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMPYRA

Approved Use

AMPYRA (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 Date

1.2641184E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
23.77 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
246.48 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
0.16 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
97%
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

Doses

DosePopulationAdverse 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%)
Myocardial infarction (1.1%)
Sources: Page: p.3
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
Consciousness decreased
Memory loss
Hypophonia
Structural brain disorders NEC
Sources: Page: p.3
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
Confusion
Sources: Page: p.3
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%)
Balance disorder (0.5%)
Dizziness (0.5%)
Confusional state (0.5%)
Sources: Page: p.2
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

AEs

AESignificanceDosePopulation
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
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
weak [IC50 195 uM]
weak [IC50 270 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
minor
minor
minor
minor
minor
minor
minor
minor
minor
minor
minor
no
Tox targets
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
KCNA10: a novel ion channel functionally related to both voltage-gated potassium and CNG cation channels.
2000 Jun
Inhibition of vesicular glutamate storage and exocytotic release by Rose Bengal.
2001 Apr
Effects of phosphodiesterase inhibitors on hypoxic pulmonary vasoconstriction. Influence of K(+) channels and nitric oxide.
2001 Apr 6
Distinguishing cochlear pathophysiology in 4-aminopyridine and furosemide treated ears using a nonlinear systems identification technique.
2001 Feb
H3 receptor-mediated inhibition of intestinal acetylcholine release: pharmacological characterization of signal transduction pathways.
2001 Feb
Pharmacological properties of excitation-contraction mechanisms in isolated mouse left atria.
2001 Feb
Modulation of diaphragm action potentials by K(+) channel blockers.
2001 Feb
Swim stress alters the behavioural response of mice to GABA-related and some GABA-unrelated convulsants.
2001 Feb
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
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
Three types of K(+) currents in murine osteocyte-like cells (MLO-Y4).
2001 Jan
Direct depolarization and antidromic action potentials transiently suppress dendritic IPSPs in hippocampal CA1 pyramidal cells.
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
Dendritic coincidence detection of EPSPs and action potentials.
2001 Jan
Two kinds of transient outward currents, I(A) and I(Adepol), in F76 and D1 soma membranes of the subesophageal ganglia of Helix aspersa.
2001 Jan 1
Localization and mechanisms of action of cannabinoid receptors at the glutamatergic synapses of the mouse nucleus accumbens.
2001 Jan 1
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
Role of K+ -channels in homotaurine-induced analgesia.
2001 Jun
Alterations in a redox oxygen sensing mechanism in chronic hypoxia.
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
Functional and molecular expression of a voltage-dependent K(+) channel (Kv1.1) in interstitial cells of Cajal.
2001 Jun 1
Developmental characteristics of epileptiform activity in immature rat neocortex: a comparison of four in vitro seizure models.
2001 Jun 29
Positive and negative contractile effects of somatostatin-14 on rat ventricular cardiomyocytes.
2001 Mar
Influence of admixed carboxymethylcellulose on release of 4-aminopyridine from hydroxypropyl methylcellulose matrix tablets.
2001 Mar 23
Effects of pituitary adenylate cyclase activating polypeptide on lumbosacral preganglionic neurons in the neonatal rat spinal cord.
2001 Mar 23
Capsaicin-induced relaxation in rabbit coronary artery.
2001 May
Time-dependent distribution and neuronal localization of c-fos protein in the rat hippocampus following 4-aminopyridine seizures.
2001 May
Targeted replacement of KV1.5 in the mouse leads to loss of the 4-aminopyridine-sensitive component of I(K,slow) and resistance to drug-induced qt prolongation.
2001 May 11
Oxygen dilation in fetal pulmonary arterioles: role of K(+) channels.
2001 May 15
BTS 72664-- a novel CNS drug with potential anticonvulsant, neuroprotective, and antimigraine properties.
2001 Summer
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
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
DALFAMPRIDINE [USP MONOGRAPH]
Common 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 Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
FDA ORPHAN DRUG 18186
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
FDA ORPHAN DRUG 214205
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
FDA ORPHAN DRUG 104497
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
EMA ASSESSMENT REPORTS FAMPYRA (AUTHORIZED: MULTIPLE SCLEROSIS)
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
EU-Orphan Drug EU/3/07/458
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
NDF-RT N0000192795
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
FDA ORPHAN DRUG 713019
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
LIVERTOX 259
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
WHO-ATC N07XX07
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
WHO-VATC QN07XX07
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
EPA PESTICIDE CODE 69201
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
Code System Code Type Description
INN
7283
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
PUBCHEM
1727
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
MERCK INDEX
M4072
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY Merck Index
HSDB
6037
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
IUPHAR
2416
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
DRUG CENTRAL
4163
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
NCI_THESAURUS
C76777
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
EPA CompTox
504-24-5
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
LACTMED
Dalfampridine
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
CAS
504-24-5
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-987-9
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
USP_CATALOG
1162454
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY USP-RS
MESH
D015761
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
FDA UNII
BH3B64OKL9
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
EVMPD
SUB07505MIG
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
DRUG BANK
DB06637
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
WIKIPEDIA
4-AMINOPYRIDINE
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
ChEMBL
CHEMBL284348
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY
RXCUI
897018
Created by admin on Sat Jun 26 07:05:38 UTC 2021 , Edited by admin on Sat Jun 26 07:05:38 UTC 2021
PRIMARY RxNorm