Guanfacine

Guanfacine Basic information
Product Name:Guanfacine
Synonyms:Guanfacine;1-(α-Oxo-2,6-dichlorophenethyl)guanidine;2-(2,6-Dichlorophenylacetyl)guanidine;C07037;BenzeneacetaMide, N-(aMinoiMinoMethyl)-2,6-dichloro-;[(2,6-Dichlorophenyl)acetyl]guanidine;N-carbaMiMidoyl-2-(2,6-dichlorophenyl)acetaMide;N-Amidino-2-[2,6-dichlorophenyl] acetamide
CAS:29110-47-2
MF:C9H9Cl2N3O
MW:246.09
EINECS:249-442-8
Product Categories:Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:29110-47-2.mol
Guanfacine Structure
Guanfacine Chemical Properties
Melting point 227-230?C
density 1.50±0.1 g/cm3(Predicted)
storage temp. Refrigerator
solubility Soluble in DMSO
form Powder
pka11.92±0.46(Predicted)
BCS Class1
Safety Information
MSDS Information
Guanfacine Usage And Synthesis
Chemical PropertiesWhite Solid
OriginatorEstulic,Sandoz,Switz.,1980
UsesCentrally acting α-adrenoceptor agonist. Antihypertensive.
UsesGuanfacine centrally acting α-adrenoceptor agonist. Guanfacine is an antihypertensive.
DefinitionChEBI: Guanfacine is a member of acetamides.
Manufacturing Process2,6-Dichlorophenyl-acetyl-guanidine: A solution of 3.245 g (0.055 mol) of guanidine in isopropanol is added to a solution of 11.7 g (0.05 mol) of 2,6- dichlorophenyl-acetic acid ethyl ester (BP 142°C to 143°C/12 mm of Hg) in 20cc of isopropanol. The reaction mixture is allowed to stand overnight and is subsequently concentrated by evaporation. After recrystallizing the residue from methanol/ether 2,6-dichlorophenyl-acetyl-guanidine is obtained in the form of white grains having a MP of 225°C to 227°C.
2,6-Dichlorophenyl-acetyl-guanidine hydrochloride: A solution of 5.6 g (0.025 mol) of 2,-dichlorophenylacetic acid chloride (BP 137°C to 138°C/12 mm of Hg) in 10 cc of toluene is added dropwise to a mixture of 4.5 g (0.076 mol) of guanidine and 60 cc of toluene. The reaction mixture is allowed to stand at room temperature for 20 minutes, is then heated on a steam bath for 2 hours and is subsequently cooled. The resulting precipitate is filtered off and washed twice with 25 cc amounts of water in order to separate the guanidine hydrochloride. The residue (2,6-dichlorophenyl-acetyl-guanidine) is washed with chloroform for further purification and is then dissolved in 50 cc of isopropanol. The pH-value of the solution is adjusted to 6 with ethanolic hydrochloric acid and the solution is cooled. The resulting white needles are again washed with chloroform. The resulting 2.6-dichlorophenyl-acetylguanidine hydrochloride has a MP of 213°C to 216°C.
Brand nameTenex (Dr. Reddy’s).
Therapeutic FunctionAntihypertensive
General DescriptionGuanfacine is more selective for 2-receptors than isclonidine. Their mechanism of action is the same as that ofclonidine. Differences between clonidine and its twoanalogs are seen in their elimination half-life values and intheir metabolism and urinary excretion patterns. The eliminationhalf-life of clonidine ranges from 20 to 25 hours,whereas that for guanfacine is about 17 hours. Guanabenzhas the shortest DOA of these three agents, with a half-lifeof about 6 hours. Clonidine and guanfacine are excretedunchanged in the urine to the extent of 60% and 50%,respectively. Very little of guanabenz is excreted unchangedin the urine.
SynthesisGuanfacin, N-amidino-2-(2,6-dichlorophenyl)acetamide (22.3.2), is also synthesized in a very easy synthesis of reacting the acid chloride or ester of 2,6- dichlorophenylacetic acid with guanidine.

Synthesis_29110-47-2

Guanfacine Preparation Products And Raw materials
Raw materialsGUANIDINE-->Hydrochloric acid-->2,6-Dichlorophenylacetic acid chloride
Fluphenazine decanoate Robenidine hydrochloride Propionyl chloride Unii-4bmh7izt98 Clonidine Memantine 2,6-DICHLOROPHENYLACETAMIDE GUANFACINE HCL,GUANFACINE HYDROCHLORIDE SALT,GUANFACINE HYDROCHLORIDE Guanfacine-13C, 15N3 2,6-DICHLOROPHENETHYLAMINE GUANFACINE HYDROCHLORIDE,GUANFACINE HYDROCHLORIDE SALT,GUANFACINE HCL Guanfacine GUANFACINE HCL USP(CRM STANDARD)

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