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Guanfacine

CAS No.29110-47-2
Chemical Name:Guanfacine
CBNumber:CB3875216
Molecular Formula:C9H9Cl2N3O
Formula Weight:246.09
MOL File:29110-47-2.mol

Guanfacine Property

Melting point 227-230?C
Density 1.50±0.1 g/cm3(Predicted)
storage temp. Refrigerator
solubility Soluble in DMSO
form Powder
pka 11.92±0.46(Predicted)
color White to off-white
BCS Class 1
EWG's Food Scores 1
FDA UNII 30OMY4G3MK
ATC code C02AC02

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H301
Precautionary statements P264-P270-P301+P310-P321-P330-P405-P501

Guanfacine Chemical Properties,Usage,Production

Chemical Properties White Solid
Originator Estulic,Sandoz,Switz.,1980
Uses Centrally acting α-adrenoceptor agonist. Antihypertensive.
Uses Guanfacine centrally acting α-adrenoceptor agonist. Guanfacine is an antihypertensive.
Definition ChEBI: Guanfacine is a member of acetamides.
Manufacturing Process 2,6-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 name Tenex (Dr. Reddy’s).
Therapeutic Function Antihypertensive
General Description Guanfacine 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.
Synthesis Guanfacin, 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.