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SML0325

Sigma-Aldrich

Retigabine

≥98% (HPLC)

Synonym(s):

D-23129, Ezogabine, N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic acid ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C16H18FN3O2
CAS Number:
150812-12-7
Molecular Weight:
303.33
Beilstein:
8072099
MDL number:
MFCD04307735
UNSPSC Code:
12352200
PubChem Substance ID:
329825330
NACRES:
NA.77

Quality Level

100

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

Gene Information

human ... KCNQ1(3784) , KCNQ2(3785) , KCNQ3(3786) , KCNQ4(9132) , KCNQ5(56479)

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Biochem/physiol Actions

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

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301 + H331,H410

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Michele A Faulkner et al.
Expert opinion on drug safety, 12(6), 847-855 (2013-07-26)
Complex-partial seizures are frequently resistant to antiepileptic therapy. Two new medications with mechanisms of action novel within the antiepileptic class have recently received approval for the adjunctive treatment of partial (focal) seizures. A Medline search was conducted to identify preclinical
Philip N Patsalos et al.
Expert opinion on pharmacotherapy, 13(5), 699-715 (2012-03-13)
The search for new, more effective antiepileptic drugs (AEDs) continues. The three most recently approved drugs, the so-called third-generation AEDs, include lacosamide, retigabine and eslicarbazepine acetate and are licensed as adjunctive treatment of partial epilepsy in adults. For the above
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
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
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
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