10289. Retigabine

Nomenclature

CAS number: 150812-12-7
N-[2-Amino-4-[[(4-fluorophenyl)methyl]amino]phenyl]carbamic acid ethyl ester; 2-amino-4-(4-fluorobenzylamino)-1-ethoxycarbonylaminobenzene; N-[2-amino-4-(4-fluorobenzylamino)phenyl] carbamic acid ethyl ester; D-23129.
C16H18FN3O2; mol wt 303.33.
C 63.35%, H 5.98%, F 6.26%, N 13.85%, O 10.55%.

Description and references

Neuronal potassium channel opener acting at Kv7.2-7.5 (KCNQ2-5) channels. Prepn: H.-R. Dieter et al., DE 4200259; eidem, US 5384330 (1993, 1995 both to Asta Medica). HPLC/MS/MS determn in plasma: N. G. Knebel et al., J. Chromatogr. B 748, 97 (2000) DOI. LC/MS/MS determn of the active, N-acetyl metabolite in plasma: W. Bu et al., J. Chromatogr. B 852, 465 (2007) DOI PubMed. Characterization of binding site and channel activation: T. V. Wuttke et al., Mol. Pharmacol. 67, 1009 (2005) DOI PubMed; A. Schenzer et al., J. Neurosci. 25, 5051 (2005) DOI PubMed. Clinical pharmacokinetics: G. M. Ferron et al., J. Clin. Pharmacol. 42, 175 (2002) DOI PubMed. Clinical evaluation in partial-onset seizures: R. J. Porter et al., Neurology 68, 1197 (2007) DOI PubMed. Review of development and pharmacology: G. Blackburn-Munro et al., CNS Drug Rev. 11, 1-20 (2005) PubMed; and clinical experience in epilepsy: R. J. Porter et al., Neurotherapeutics 4, 149-154 (2007) DOI PubMed.

Chemical structure

Properties

White to slightly colored, odorless, tasteless, non-hygroscopic crystalline powder, mp 138-145°. pKa 10.8.

Derivative

Dihydrochloride.

Nomenclature

CAS number: 150812-13-8
D-20443.
C16H18FN3O2.2HCl; mol wt 376.25.
C 51.08%, H 5.36%, F 5.05%, N 11.17%, O 8.50%, Cl 18.85%.

Properties

Colorless to slightly pink crystals from ethanol ether, mp 182-186°. Hygroscopic.

Therapeutic Category

Anticonvulsant.

Keywords

Potassium Channel Activator/Opener; Anticonvulsant