2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

• ChemBase编号: 96
• 分子式: C12H18N2O4
• 平均质量: 254.28232
• 单一同位素质量: 254.12665707
• SMILES: OC(c1c(OC)ccc(OC)c1)CNC(=O)CN
• Canonical SMILES: COc1ccc(cc1C(CNC(=O)CN)O)OC
• InChI: InChI=1S/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16)
• InChIKey: PTKSEFOSCHHMPD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide
• IUPAC传统名: midodrine
• 商标名: ProAmatine
• 别名: Midodrina [INN-Spanish]; Midodrine HCL; midodrine hydrochloride; Midodrinum [INN-Latin]; Midodrin; Midodrine

登记号

• CAS号: 133163-28-7
• PubChem SID: 46507373; 160963559
• PubChem CID: 4195

理论计算性质

JChem

• Log P: -0.95194644
• 摩尔折射率: 66.2238 cm^3
• 极化性: 26.112099 Å^3
• 极化表面积: 93.81 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true
• Acid pKa: 13.765054
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -3.4449556
• LogD (pH = 7.4): -1.7617897

ALOGPS 2.1

• LOG S: -1.76
• 溶解度: 4.45e+00 g/l
• Log P: -0.49

分子性质

理化性质

• 溶解度: Soluble
• 疏水性(logP): -0.5

详细说明

DrugBank - DB00211

• Drug Groups: approved
• Description: An ethanolamine derivative that is an adrenergic alpha agonist. It is used as a vasoconstrictor agent in the treatment of hypotension. [PubChem]
• Indication: For the treatment of symptomatic orthostatic hypotension (OH).
• Pharmacology: Midodrine is a prodrug, i.e., the therapeutic effect of orally administered midodrine is due to the major metabolite desglymidodrine formed by deglycination of midodrine. Desglymidodrine diffuses poorly across the blood-brain barrier, and is therefore not associated with effects on the central nervous system. Administration of midodrine results in a rise in standing, sitting, and supine systolic and diastolic blood pressure in patients with orthostatic hypotension of various etiologies. Standing systolic blood pressure is elevated by approximately 15 to 30 mmHg at 1 hour after a 10-mg dose of midodrine, with some effect persisting for 2 to 3 hours. Midodrine has no clinically significant effect on standing or supine pulse rates in patients with autonomic failure.
• Toxicity: Symptoms of overdose could include hypertension, piloerection (goosebumps), a sensation of coldness and urinary retention. The single doses that would be associated with symptoms of overdosage or would be potentially life- threatening are unknown. The oral LD₅₀ is approximately 30 to 50 mg/kg in rats, 675 mg/kg in mice, and 125 to 160 mg/kg in dogs. Desglymidodrine is dialyzable.
• Affected Organisms: Humans and other mammals
• Biotransformation: Thorough metabolic studies have not been conducted, but it appears that deglycination of midodrine to desglymidodrine takes place in many tissues, and both compounds are metabolized in part by the liver.
• Absorption: Rapidly absorbed following oral administration. The absolute bioavailability of midodrine (measured as desglymidodrine) is 93% and is not affected by food.
• Half Life: The plasma levels of the prodrug peak after about half an hour, and decline with a half-life of approximately 25 minutes, while the metabolite reaches peak blood concentrations about 1 to 2 hours after a dose of midodrine and has a half-life of about 3 to 4 hours.
• Clearance: * Renal cl=385 mL/minute
• References: Hebenstreit G: [Treatment of hypotension caused by psychopharmacological drugs (author's transl)] Wien Med Wochenschr. 1981 Feb 28;131(4):109-12. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Hebenstreit G: [Treatment of hypotension caused by psychopharmacological drugs (author's transl)] Wien Med Wochenschr. 1981 Feb 28;131(4):109-12. Pubmed