Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H6N2.ClH |
| Molecular Weight | 130.575 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NC1=CC=NC=C1
InChI
InChIKey=CBFZWGRQXZYRRR-UHFFFAOYSA-N
InChI=1S/C5H6N2.ClH/c6-5-1-3-7-4-2-5;/h1-4H,(H2,6,7);1H
| Molecular Formula | C5H6N2 |
| Molecular Weight | 94.1145 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
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 Date2010 |
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: |
unhealthy, 52.1 ± 8.8 Health Status: unhealthy Age Group: 52.1 ± 8.8 Sex: M+F Sources: |
Disc. AE: Seizure, Myocardial infarction... AEs leading to discontinuation/dose reduction: Seizure (1.1%) Sources: Myocardial infarction (1.1%) |
300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Weakness, Consciousness decreased... AEs leading to discontinuation/dose reduction: Weakness Sources: Consciousness decreased Memory loss Hypophonia Structural brain disorders NEC |
40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sex: F Sources: |
Disc. AE: Complex partial seizures, Confusion... AEs leading to discontinuation/dose reduction: Complex partial seizures Sources: Confusion |
60 mg single, oral Overdose Dose: 60 mg Route: oral Route: single Dose: 60 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Mental state abnormal... AEs leading to discontinuation/dose reduction: Mental state abnormal Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Seizures... AEs leading to discontinuation/dose reduction: Seizures Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Headache, Balance disorder... AEs leading to discontinuation/dose reduction: Headache (0.5%) Sources: Balance disorder (0.5%) Dizziness (0.5%) Confusional state (0.5%) |
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: |
unhealthy, 52.1 ± 8.8 Health Status: unhealthy Age Group: 52.1 ± 8.8 Sex: M+F Sources: |
| 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: |
unhealthy, 52.1 ± 8.8 Health Status: unhealthy Age Group: 52.1 ± 8.8 Sex: M+F Sources: |
| Consciousness decreased | Disc. AE | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
| Hypophonia | Disc. AE | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
| Memory loss | Disc. AE | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
| Structural brain disorders NEC | Disc. AE | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
| Weakness | Disc. AE | 300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
| Complex partial seizures | Disc. AE | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sex: F Sources: |
| Confusion | Disc. AE | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sex: F Sources: |
| Mental state abnormal | Disc. AE | 60 mg single, oral Overdose Dose: 60 mg Route: oral Route: single Dose: 60 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| General rules for the packing of hydrogen-bonded crystals as derived from the analysis of squaric acid anions: aminoaromatic nitrogen base co-crystals. | 2001-08 |
|
| Resolving the gating charge movement associated with late transitions in K channel activation. | 2001-08 |
|
| A model for 4-aminopyridine action on K channels: similarities to tetraethylammonium ion action. | 2001-08 |
|
| Fenfluramine-induced pulmonary vasoconstriction: role of serotonin receptors and potassium channels. | 2001-08 |
|
| The relaxation induced by S-nitroso-glutathione and S-nitroso-N-acetylcysteine in rat aorta is not related to nitric oxide production. | 2001-08 |
|
| A novel mechanical dissociation technique for studying acutely isolated maturing Drosophila central neurons. | 2001-07-30 |
|
| High glucose impairs voltage-gated K(+) channel current in rat small coronary arteries. | 2001-07-20 |
|
| Lamotrigine inhibition of glutamate release from isolated cerebrocortical nerve terminals (synaptosomes) by suppression of voltage-activated calcium channel activity. | 2001-07-20 |
|
| Gap junctions synchronize the firing of inhibitory interneurons in guinea pig hippocampus. | 2001-07-13 |
|
| Diversity of K+ channels in circular smooth muscle of opossum lower esophageal sphincter. | 2001-07 |
|
| 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. | 2001-07 |
|
| Imaging of 4-AP-induced, GABA(A)-dependent spontaneous synchronized activity mediated by the hippocampal interneuron network. | 2001-07 |
|
| KT3.2 and KT3.3, two novel human two-pore K(+) channels closely related to TASK-1. | 2001-07 |
|
| Long-term recordings of networks of immortalized GnRH neurons reveal episodic patterns of electrical activity. | 2001-07 |
|
| Relaxation to authentic nitric oxide and SIN-1 in rat isolated mesenteric arteries: variable role for smooth muscle hyperpolarization. | 2001-07 |
|
| Bcl-2 decreases voltage-gated K+ channel activity and enhances survival in vascular smooth muscle cells. | 2001-07 |
|
| Developmental characteristics of epileptiform activity in immature rat neocortex: a comparison of four in vitro seizure models. | 2001-06-29 |
|
| "Use-dependent" effects of cisapride on postrest action potentials in rabbit ventricular myocardium. | 2001-06-22 |
|
| Theoretical analysis of the molecular determinants responsible for the K(+) channel blocking by aminopyridines. | 2001-06-15 |
|
| Potassium channel blocker TEA prevents CA1 hippocampal injury following transient forebrain ischemia in adult rats. | 2001-06-08 |
|
| Mechanisms underlying presynaptic facilitatory effect of cyclothiazide at the calyx of Held of juvenile rats. | 2001-06-01 |
|
| Functional and molecular expression of a voltage-dependent K(+) channel (Kv1.1) in interstitial cells of Cajal. | 2001-06-01 |
|
| Skin surface electric potential induced by ion-flux through epidermal cell layers. | 2001-06-01 |
|
| Dopamine D4 receptor-deficient mice display cortical hyperexcitability. | 2001-06-01 |
|
| Membrane resonance and subthreshold membrane oscillations in mesencephalic V neurons: participants in burst generation. | 2001-06-01 |
|
| Role of K+ -channels in homotaurine-induced analgesia. | 2001-06 |
|
| Normal coordinate analysis of 4-aminopyridine. Effect of substituent on pyridine ring in metal complexes of 4-substituted pyridines. | 2001-06 |
|
| Focal cooling rapidly terminates experimental neocortical seizures. | 2001-06 |
|
| Pharmacological modulation of SK3 channels. | 2001-06 |
|
| Tonotopic map of potassium currents in chick auditory hair cells using an intact basilar papilla. | 2001-06 |
|
| Alterations in a redox oxygen sensing mechanism in chronic hypoxia. | 2001-06 |
|
| Superfusion of synaptosomes to study presynaptic mechanisms involved in neurotransmitter release from rat brain. | 2001-06 |
|
| Synchronized Ca2+ signals mediated by Ca2+ action potentials in the hippocampal neuron network in vitro. | 2001-06 |
|
| Potassium channels regulate tone in rat pulmonary veins. | 2001-06 |
|
| minK-related peptide 1 associates with Kv4.2 and modulates its gating function: potential role as beta subunit of cardiac transient outward channel? | 2001-05-25 |
|
| Stretch-dependent potassium channels in murine colonic smooth muscle cells. | 2001-05-15 |
|
| Oxygen dilation in fetal pulmonary arterioles: role of K(+) channels. | 2001-05-15 |
|
| Inhibition of glutamate release by BIA 2-093 and BIA 2-024, two novel derivatives of carbamazepine, due to blockade of sodium but not calcium channels. | 2001-05-15 |
|
| 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. | 2001-05-11 |
|
| Ion channels associated with the ectopic discharges generated after segmental spinal nerve injury in the rat. | 2001-05-04 |
|
| A redox-based mechanism for the contractile and relaxing effects of NO in the guinea-pig gall bladder. | 2001-05-01 |
|
| Capsaicin-induced relaxation in rabbit coronary artery. | 2001-05 |
|
| Time-dependent distribution and neuronal localization of c-fos protein in the rat hippocampus following 4-aminopyridine seizures. | 2001-05 |
|
| The expression and regulation of depolarization-activated K+ channels in the insulin-secreting cell line INS-1. | 2001-04 |
|
| Differential expression of KV and KCa channels in vascular smooth muscle cells during 1-day culture. | 2001-04 |
|
| Modulation of voltage-dependent K+ channel current in vascular smooth muscle cells from rat mesenteric arteries. | 2001-03-15 |
|
| The effects of different 4-aminopyridine and morphine combinations on the intensity of morphine abstinence. | 2001-03 |
|
| Chloride distribution in the CA1 region of newborn and adult hippocampus by light microscopic histochemistry. | 2001-02 |
|
| The effect of acidosis on the ECG of the rat heart. | 2001-01 |
|
| BTS 72664-- a novel CNS drug with potential anticonvulsant, neuroprotective, and antimigraine properties. | 2001 |
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.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
897AWS9WZQ
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| Record Status |
Validated (UNII)
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| Record Version |
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