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Guanfacine

Basic information Safety Supplier Related

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
  • Guanfacine Solution, 100ppm
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
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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
pka
11.92±0.46(Predicted)
BCS Class
1
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Guanfacine Usage And Synthesis

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.

GuanfacineSupplier

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