150812-13-8

Basic information

• Product Name: Retigabine Dihydrochloride
• Synonyms: D 20443;Ethyl [2-amino-4-[[(4-fluorophenyl)methyl]amino]phenyl]carbamate Dihydrochloride;N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic Acid Ethyl Ester Dihydrochloride;Retigabine Dihydrochloride;Retigabine 2HCL;Retigabine HCl;D 20443 dihydrochloride;D20443 dihydrochloride
• CAS NO: 150812-13-8
• Molecular Formula: C16H20Cl2FN3O2
• Molecular Weight: 339.79
• EINECS: 2017-001-1
• Product Categories: Chemical Amines;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;API
• Mol File: 150812-13-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 168-170°C
• Boiling Point: 430 °C at 760 mmHg
• Flash Point: 213.9 °C
• Appearance: Off-white powder
• Vapor Pressure: 1.34E-07mmHg at 25°C
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: ≥18.8 mg/mL in DMSO; ≥52.4 mg/mL in H2O with gentle warming; ≥8.71 mg/mL in EtOH with gentle warming and ultrasonic
• CAS DataBase Reference: Retigabine Dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Retigabine Dihydrochloride(150812-13-8)
• EPA Substance Registry System: Retigabine Dihydrochloride(150812-13-8)

Safety Data

• Hazardous Substances Data: 150812-13-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Powder

Biological Activity

retigabine is a first-in-class k+ channel (kcnq) opener. kcnq channels are reported to be expressed predominantly in neurons and are critical determinants of cellular excitability, as shown by the occurrence of human genetic mutations in kcnq channels which underlie inheritable disorders including the syndrome of benign familial neonatal convulsions.

in vitro

retigabine was found to combine a novel mode of actions, which were namely potassium channel opening (kcnq2, kcnq3 as well as kcnq4 channels). retigabine also showed activities with some potentiation of gamma amino butyric acid (gaba)-evoked currents at its higher concentrations [1].

in vivo

animal models of epileptic seizures showed that retigabine treatment was effective at an oral dose as low as 0.01 mg/kg. studies performed in mice also indicated that combining retigabine with another anticonvulsant agent leads to an additive effect [1].

references

[1] ferron gm,patat a,parks v,rolan p,troy sm. lack of pharmacokinetic interaction between retigabine and phenobarbitone at steady-state in healthy subjects. br j clin pharmacol.2003 jul;56(1):39-45.

InChI:InChI=1/C16H18FN3O2.ClH/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);1H

Upstream product

• 150812-12-7 Retigabine 
• 73895-87-1 5-amino-2-ethoxycarbonylaminonitrobenzene 
• 721943-05-1 1-ethoxycarbonylamino-4-phthalimidobenzene 
• 150812-24-1 2-ethoxycarbonylamino-5-phthalimidonitrobenzene 
• 57399-97-0 N-(4-aminophenyl)carbamic acid ethyl ester 
• 150812-23-0 2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 1314406-56-8 2-ethoxycarbonylamino-5-(4-fluorobenzylideneamino)nitrobenzene 
• 491871-67-1 4-N-[(4-fluorophenyl)methyl]benzene-1,2,4-triamine 
• 541-41-3 chloroformic acid ethyl ester 

Relevant articles and documents

SALTS OR CO-CRYSTALS OF ETHYL N-[2-AMINO-4-[(4-FLUOROPHENYL)METHYLAMINO]-PHENYL]CARBAMATE

A salt or co-crystal of ethyl N-[2-amino-4-[(4-fluorophenyl)methylamino]- phenyl]carbamate and one acid selected from the group consisting of hydrobromic acid, hydrochloric acid, methanesulphonic acid, benzenesulphonic acid, fumaric acid and salicylic aci

DIETHYL 4-(4-FLUOROBENZYLAMINO)-1,2-PHENYLENEDICARBAMATE, AND SALTS THEREOF

Disclosed are diethyl 4-(4-fluorobenzylamino)-l,2-phenylenedicarbamate (IV) and salts thereof, which are useful as reference markers and reference standards for analyzing samples comprising retigabine or salts thereof. Also disclosed is a process for prep