Guanfacine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Guanfacine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Guanfacine?

The molecule Guanfacine presents a molecular formula of C9H9Cl2N3O and its IUPAC name is N-(diaminomethylidene)-2-(2,6-dichlorophenyl)acetamide.

Guanfacine (brand name Intuniv) is a long-acting, non-stimulant medication used to treat attention deficit hyperactivity disorder (ADHD). It is a second-generation alpha-2A adrenergic receptor agonist, which means it works by affecting certain chemicals in the brain that contribute to hyperactivity and impulsiveness..

Guanfacine was originally approved by the FDA in 1997 for the treatment of hypertension (high blood pressure). It was approved for the treatment of ADHD in 2009..

How does guanfacine work?.

Guanfacine works by affecting certain chemicals in the brain that contribute to hyperactivity and impulsiveness. Specifically, it is a second-generation alpha-2A adrenergic receptor agonist..

Adrenergic receptors are found in the brain and throughout the body. They are part of the sympathetic nervous system, which is responsible for the "fight-or-flight" response..

There are two types of adrenergic receptors, alpha and beta. Guanfacine is an agonist of the alpha-2A receptor. This means it activates the receptor..

Activation of the alpha-2A receptor has been shown to reduce impulsiveness and hyperactivity in animal studies. It is thought to work by inhibiting the release of norepinephrine, a neurotransmitter that participes in attention and focus..

What are the side effects of guanfacine?.

The most common side effects of guanfacine are dry mouth, headache, drowsiness, and fatigue..

Guanfacine may also cause low blood pressure and slow heart rate. These side effects are more common when guanfacine is first started and usually go away with time..

Rare but serious side effects of guanfacine include fainting, slow heart rate, and low blood pressure. If you experience any of these side effects, call your doctor immediately..

Guanfacine may also cause weight gain. This side effect is more common in children than adults..

What are the dosage forms and strengths of guanfacine?.

Guanfacine exists as a tablet and an extended-release tablet. The tablets are available in the following strengths:.

1 mg.

2 mg.

3 mg.

4 mg.

The extended-release tablets are available in the following strengths:.

1 mg.

2 mg.

3 mg.

4 mg.

6 mg.

8 mg.

10 mg.

What is the usual dose of guanfacine?.

The starting dose of guanfacine for children and adolescents 6 to 17 years old is 2 mg once daily. The dose may be increased to 4 mg once daily after one week if needed..

The starting dose of guanfacine for adults is 1 mg once daily. The dose may be increased to 2 mg once daily after one week if needed..

Guanfacine should be taken with or without food..

If you miss a dose of guanfacine, take it as soon as possible. If it is almost time for your next dose, skip the missed dose and continue with your regular dosing schedule. Do not take two doses of guanfacine at the same time..

What are the warnings and precautions for guanfacine?.

Guanfacine may cause drowsiness and slow reflexes. Do not drive or operate heavy machinery until you know how guanfacine affects you..

Guanfacine may cause low blood pressure and slow heart rate. These side effects are more common when guanfacine is first started and usually go away with time..

Guanfacine may also cause weight gain. This side effect is more common in children than adults..

Guanfacine should be used with caution in people with heart problems, including congestive heart failure, heart block, and low blood pressure..

Guanfacine should be used with caution in people with kidney problems..

Guanfacine should be used with caution in people with liver problems..

Guanfacine should be used with caution in people with mental illness..

Guanfacine should be used with caution in people with a history of substance abuse..

Guanfacine should be used with caution in people with a history of fainting..

Guanfacine should be used with caution in people with a history of slow heart rate..

Guanfacine should be used with caution in people with a history of low blood pressure..

Guanfacine should be used with caution in people who are taking other medications that can cause low blood pressure or slow heart rate..

Guanfacine should be used with caution in people who are taking medications that can cause weight gain..

The safety and efficacy of guanfacine in children.

3D structure

Cartesian coordinates

Geometry of Guanfacine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Guanfacine INJOMKTZOLKMBF-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Guanfacine

 

Molecule descriptors

 
IUPAC nameN-(diaminomethylidene)-2-(2,6-dichlorophenyl)acetamide
InChI codeInChI=1S/C9H9Cl2N3O/c10-6-2-1-3-7(11)5(6)4-8(15)14-9(12)13/h1-3H,4H2,(H4,12,13,14,15)
InChI KeyINJOMKTZOLKMBF-UHFFFAOYSA-N
SMILESNC(N)=NC(=O)Cc1c(Cl)cccc1Cl

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (2,6-dichlorophenylacetyl)-guanidine
  • 29110-47-2
  • 30OMY4G3MK
  • A902647
  • A918619
  • AB01563079_01
  • BCP09647
  • BDBM81984
  • BPBio1_000415
  • BSPBio_000377
  • Benzeneacetamide, N-(aminoiminomethyl)-2,6-dichloro-
  • C07037
  • CAS_29110-47-2
  • CCG-204609
  • D08031
  • DB01018
  • Estulic
  • FT-0669067
  • FT-0669068
  • GTPL522
  • GUANFACINE
  • Guanfacina
  • Guanfacine
  • Guanfacine (INN)
  • Guanfacine-13C-15N3
  • Guanfacinum
  • HY-17416A
  • J-017394
  • L000286
  • L013430
  • Lopac-G-1043
  • Lopac0_000519
  • MRF-0000019
  • N-(Diaminomethyliden)-2-(2,6-dichlorophenyl)acetamid
  • N-(diaminomethylidene)-2-(2,6-dichlorophenyl)acetamide
  • N-amidino-2-(2,6-dichlorophenyl)acetamide
  • N-carbamimidoyl-2-(2,6-dichlorophenyl)acetamide
  • NCGC00015469-01
  • NCGC00015469-02
  • NCGC00015469-03
  • NCGC00015469-04
  • NCGC00015469-05
  • NCGC00015469-06
  • NCGC00015469-07
  • NCGC00024950-01
  • NCGC00024950-02
  • NCGC00024950-03
  • NSC 759121
  • NSC-759121
  • NSC_3519
  • Prestwick0_000339
  • Prestwick1_000339
  • Prestwick2_000339
  • Prestwick3_000339
  • Q5613599
  • RASPBERRYKETONEGLUCOSIDE
  • SDCCGSBI-0050502.P002
  • SPD 503
  • Tocris-1030
  • [(2,6-Dichlorophenyl)acetyl]guanidine hydrochloride;Guanfacine HCl
  • [(2,6-dichlorophenyl)acetyl]guanidine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3872738
  • CAS-29110-48-3
  • UNII-30OMY4G3MK
  • AKOS030255657
  • BRD-K32830106-003-03-0
  • BRD-K32830106-003-11-3
  • DTXSID9046944
  • CHEMBL862
  • CHEBI:5558
  • EINECS 249-442-8
  • SPBio_002298
  • SCHEMBL35094

Physico-Chemical properties

IUPAC nameN-(diaminomethylidene)-2-(2,6-dichlorophenyl)acetamide
Molecular formulaC9H9Cl2N3O
Molecular weight246.093
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity60.34
LogP2.7
Topological polar surface area81.5

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.