N-carbamimidoyl-2-(2,6-dichlorophenyl)acetamide

• ChemBase ID: 891
• Molecular Formular: C9H9Cl2N3O
• Molecular Mass: 246.09326
• Monoisotopic Mass: 245.01226728
• SMILES: c1(CC(=O)NC(=N)N)c(cccc1Cl)Cl
• Canonical SMILES: O=C(Cc1c(Cl)cccc1Cl)NC(=N)N
• InChI: InChI=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)
• InChIKey: INJOMKTZOLKMBF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-carbamimidoyl-2-(2,6-dichlorophenyl)acetamide
• IUPAC Traditional name: @guanfacine; guanfacine
• Brand Name: Estulic; Tenex; Intuniv
• Synonyms: SPD 503; Guanfacine; Guanfacina [INN-Spanish]; Guanfacine HCl; Guanfacine Hydrochloride; Guanfacinum [INN-Latin]; guanfacine; N-(Aminoiminomethyl)-2,6-dichlorobenzeneacetamide; N-Amidino-2-(2,6-dichlorophenyl)acetamide; [(2,6-Dichlorophenyl)acetyl]guanidine; Guanfascine; Guarfacine; Guanfacin

Database IDs

• CAS Number: 29110-47-2
• PubChem SID: 160964354; 46506169
• PubChem CID: 3519

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.937506
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.58233494
• LogD (pH = 7.4): 1.666594
• Log P: 1.7370318
• Molar Refractivity: 69.6341 cm^3
• Polarizability: 22.76446 Å^3
• Polar Surface Area: 78.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.28
• LOG S: -3.25
• Solubility (Water): 1.39e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1892 mg/L; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 200-203°C
• Hydrophobicity(logP): 1.7

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB01018

• Drug Groups: approved; investigational
• Description: A centrally acting antihypertensive agent. The drug lowers both systolic and diastolic blood pressure by activating the central nervous system alpha-2 adrenoreceptors, which results in reduced sympathetic outflow leading to reduced vascular tone. Its adverse reactions include dry mouth, sedation, and constipation. [PubChem]
• Indication: For use alone or in combination with other classes of antihypertensive agents in the management of hypertension. Has also been used for the treatment of attention deficit hyperactivity disorder (ADHD) in pediatric patients.
• Pharmacology: Guanfacine is a phenylacetyl-guanidine derivative hypotensive and a centrally-acting, alpha(2)-adrenergic receptor agonist used alone or in combination with other drugs for the treatment of hypertension.
• Toxicity: Symptoms of overdose include drowsiness, lethargy, bradycardia and hypotension. LD₅₀=165mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Rapid and complete, with an oral bioavailability of approximately 80%.
• Half Life: 17 hours (range 10-30 hours)
• Protein Binding: Approximately 70% bound to plasma proteins, independent of drug concentration.
• Elimination: In individuals with normal renal function, guanfacine and its metabolites are excreted primarily in the urine.
• Distribution: * 6.3 L/kg
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - G816000

Guanfacine centrally acting α-adrenoceptor agonist. Guanfacine is an antihypertensive.

REFERENCES

• Urosevic, D., et al.: Br. J. Pharmacol., 142, 609 (2004)
• Remko, M., et al.: Bioorg. Med. Chem., 14, 1715 (2004)
• Nikolic, K., et al.: Bioorg. Med. Chem., 16, 7134 (2008).