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SML0325

Sigma-Aldrich

Retigabine

≥98% (HPLC)

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Synonym(s):
D-23129, Ezogabine, N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic acid ethyl ester
Empirical Formula (Hill Notation):
C16H18FN3O2
CAS Number:
Molecular Weight:
303.33
Beilstein/REAXYS Number:
8072099
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

drug control

USDEA Schedule V

color

white to light brown

solubility

DMSO: >15 mg/mL

storage temp.

room temp

SMILES string

FC1=CC=C(CNC2=CC(N)=C(NC(OCC)=O)C=C2)C=C1

InChI

1S/C16H18FN3O2/c1-2-22-16(21)20-15-8-7-13(9-14(15)18)19-10-11-3-5-12(17)6-4-11/h3-9,19H,2,10,18H2,1H3,(H,20,21)

InChI key

PCOBBVZJEWWZFR-UHFFFAOYSA-N

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1 of 4

This Item
90221SML1738SML0284
Retigabine ≥98% (HPLC)

SML0325

Retigabine

Retigabine analytical standard

90221

Retigabine

RL648_81 ≥98% (HPLC)

SML1738

RL648_81

Mycophenolate mofetil ≥98% (HPLC)

SML0284

Mycophenolate mofetil

assay

≥98% (HPLC)

assay

≥98.0% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

drug control

USDEA Schedule V

drug control

USDEA Schedule IV

drug control

-

drug control

-

storage temp.

room temp

storage temp.

2-8°C

storage temp.

room temp

storage temp.

room temp

solubility

DMSO: >15 mg/mL

solubility

-

solubility

DMSO: 25 mg/mL, clear

solubility

DMSO: ≥15 mg/mL

color

white to light brown

color

-

color

white to beige

color

white to beige

Biochem/physiol Actions

Retigabine (Ezogabine) is a Kv7.2-7.5 (KCNQ2-5) neuronal potassium channel opener witrh anticonvulsant activity.

pictograms

Skull and crossbonesEnvironment

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Sylvain Rheims et al.
Expert review of neurotherapeutics, 12(5), 509-517 (2012-05-04)
Ezogabine/retigabine (RTG) is a novel antiepileptic compound that activates a voltage-sensitive neuronal-specific outward potassium current that decreases neuronal excitability. RTG has been evaluated in three pivotal placebo-controlled randomized trials as adjunctive therapy in adult drug-resistant partial epilepsy. In comparison to
Emma D Deeks
CNS drugs, 25(10), 887-900 (2011-09-23)
Retigabine (ezogabine in the US) opens neuronal voltage-gated potassium channels, resulting in resting membrane potential stabilization, neuronal subthreshold excitability control and anticonvulsant effects. The clinical efficacy of adjunctive oral retigabine in adults with inadequately controlled, partial-onset seizures was demonstrated in
Carl E Stafstrom et al.
Nature reviews. Drug discovery, 10(10), 729-730 (2011-10-01)
Ezogabine (Potiga; Valeant Pharmaceuticals/GlaxoSmithKline), a potassium channel opener, was approved in June 2011 by the U.S. Food and Drug Administration (F.D.A.) for the adjunctive treatment of partial-onset seizures in adult patients. The same drug was granted marketing authorization for this
Ewa Zwierzyńska et al.
Postepy higieny i medycyny doswiadczalnej (Online), 67, 973-981 (2013-10-04)
Retigabine belongs to a new generation of antiepileptic drugs. Its mechanism of action is different from that previously known. Retigabine opens potassium channels of subfamily Kv 7, especially Kv 7.2 and Kv 7.3. The drug enhances GABA-ergic transmission. It is
Lyubov I Brueggemann et al.
Molecular pharmacology, 86(3), 330-341 (2014-06-20)
Recent research suggests that smooth muscle cells express Kv7.4 and Kv7.5 voltage-activated potassium channels, which contribute to maintenance of their resting membrane voltage. New pharmacologic activators of Kv7 channels, ML213 (N-mesitybicyclo[2.2.1]heptane-2-carboxamide) and ICA-069673 N-(6-chloropyridin-3-yl)-3,4-difluorobenzamide), have been reported to discriminate among

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