2-[4-(2,3-dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine

• ChemBase编号: 472
• 分子式: C23H25N5O5
• 平均质量: 451.4751
• 单一同位素质量: 451.18556893
• SMILES: O1C(C(=O)N2CCN(CC2)c2nc3c(c(n2)N)cc(OC)c(OC)c3)COc2c1cccc2
• Canonical SMILES: COc1cc2nc(nc(c2cc1OC)N)N1CCN(CC1)C(=O)C1COc2c(O1)cccc2
• InChI: InChI=1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
• InChIKey: RUZYUOTYCVRMRZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-[4-(2,3-dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine
• IUPAC传统名: 2-[4-(2,3-dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine; doxazosin
• 商标名: Alfadil; Cardenalin; Cardular; Cardura; Cardura-1; Cardura-2; Cardura-4; Carduran; Diblocin; Normothen; Supressin; Cardura XL
• 别名: Doxazosin mesilate; Doxazosin mesylate; Doxazosin; 2-[4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine

登记号

• CAS号: 74191-85-8
• MDL号: MFCD00800482
• PubChem SID: 46506825; 160963935
• PubChem CID: 3157

理论计算性质

JChem

• Acid pKa: 12.670158
• 质子受体: 9
• 质子供体: 1
• LogD (pH = 5.5): 0.6322931
• LogD (pH = 7.4): 1.9103665
• Log P: 2.135759
• 摩尔折射率: 121.6383 cm^3
• 极化性: 46.96491 Å^3
• 极化表面积: 112.27 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.53
• LOG S: -2.76
• 溶解度: 7.90e-01 g/l

分子性质

理化性质

• 溶解度: 24 mg/L
• 熔点: 279 - 281°C
• 疏水性(logP): 2.1; 3.532

产品相关信息

• 纯度: 95%

详细说明

DrugBank - DB00590

• Drug Groups: approved
• Description: Doxazosin is a quinazoline-derivative that selectively antagonizes postsynaptic α₁-adrenergic receptors. It may be used to mild to moderate hypertension and in the management of symptomatic benign prostatic hyperplasia (BPH). α₁-Receptors mediate contraction and hypertrophic growth of smooth muscle cells. Antagonism of these receptors leads to smooth muscle relaxation in the peripheral vasculature and prostate gland.
• Indication: For treatment and management of mild to moderate hypertension and urinary obstruction symptoms caused by BPH.
• Pharmacology: Doxazosin is an alpha-adrenergic blocking agent used to treat hypertension and benign prostatic hyperplasia. Accordingly, Doxazosin is a selective inhibitor of the alpha1 subtype of alpha adrenergic receptors. In the human prostate, Doxazosin antagonizes phenylephrine (alpha1 agonist)-induced contractions, in vitro, and binds with high affinity to the alpha1c adrenoceptor, which is thought to be the predominant functional type in the prostate. Studies in normal human subjects have shown that Doxazosin competitively antagonized the pressor effects of phenylephrine (an alpha1 agonist) and the systolic pressor effect of norepinephrine. The antihypertensive effect of Doxazosin results from a decrease in systemic vascular resistance and the parent compound Doxazosin is primarily responsible for the antihypertensive activity.
• Toxicity: Symptoms of overdose include hypotension. Oral LD₅₀ is greater than 1000 mg/kg in mice and rats.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: 65%
• Half Life: 22 hours
• Protein Binding: 98%
• Elimination: On average only 4.8% of the dose was excreted as unchanged drug in the feces and only a trace of the total radioactivity in the urine was attributed to unchanged drug.
• References: Cushman WC, Ford CE, Cutler JA, Margolis KL, Davis BR, Grimm RH, Black HR, Hamilton BP, Holland J, Nwachuku C, Papademetriou V, Probstfield J, Wright JT Jr, Alderman MH, Weiss RJ, Piller L, Bettencourt J, Walsh SM: Success and predictors of blood pressure control in diverse North American settings: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT). J Clin Hypertens (Greenwich). 2002 Nov-Dec;4(6):393-404. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

参考文献

• Cushman WC, Ford CE, Cutler JA, Margolis KL, Davis BR, Grimm RH, Black HR, Hamilton BP, Holland J, Nwachuku C, Papademetriou V, Probstfield J, Wright JT Jr, Alderman MH, Weiss RJ, Piller L, Bettencourt J, Walsh SM: Success and predictors of blood pressure control in diverse North American settings: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT). J Clin Hypertens (Greenwich). 2002 Nov-Dec;4(6):393-404. Pubmed