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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

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)

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Martin J Gunthorpe et al.
Epilepsia, 53(3), 412-424 (2012-01-10)
The pharmacologic profile of retigabine [RTG (international nonproprietary name); ezogabine, EZG (U.S. adopted name)], is different from all currently approved antiepileptic drugs (AEDs). Its primary mechanism of action (MoA) as a positive allosteric modulator of KCNQ2-5 (K(v) 7.2-7.5) ion channels
Roger J Porter et al.
Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics, 4(1), 149-154 (2007-01-03)
Retigabine is a novel antiseizure drug that acts through potassium channels and has activity in a broad range of animal models of epilepsy. It is also effective in several preclinical pain models. The drug has been extensively studied in phase
Gökce Orhan et al.
Expert opinion on pharmacotherapy, 13(12), 1807-1816 (2012-07-13)
Epilepsy is a serious and common chronic neurological disease with an urgent need for novel treatment options, because 30% of all epilepsy patients do not respond to currently available drugs. Retigabine/Ezogabine (RTG) is a third-generation antiepileptic drug (AED) with a
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
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