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

• ChemBase编号: 891
• 分子式: C9H9Cl2N3O
• 平均质量: 246.09326
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: N-carbamimidoyl-2-(2,6-dichlorophenyl)acetamide
• IUPAC传统名: @guanfacine; guanfacine
• 商标名: Estulic; Tenex; Intuniv
• 别名: 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

登记号

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

理论计算性质

JChem

• Acid pKa: 12.937506
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 0.58233494
• LogD (pH = 7.4): 1.666594
• Log P: 1.7370318
• 摩尔折射率: 69.6341 cm^3
• 极化性: 22.76446 Å^3
• 极化表面积: 78.97 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.28
• LOG S: -3.25
• 溶解度: 1.39e-01 g/l

分子性质

理化性质

• 溶解度: 1892 mg/L; DMSO; Methanol
• 外观: White Solid
• 熔点: 200-203°C
• 疏水性(logP): 1.7

安全信息

• 保存条件: Refrigerator

详细说明

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.

参考文献

• 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).