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72432-03-2 分子结构
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(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol

ChemBase编号:374
分子式:C8H17NO5
平均质量:207.22428
单一同位素质量:207.11067265
SMILES和InChIs

SMILES:
O[C@@H]1[C@H](N(C[C@H](O)[C@H]1O)CCO)CO
Canonical SMILES:
OCCN1C[C@H](O)[C@H]([C@@H]([C@H]1CO)O)O
InChI:
InChI=1S/C8H17NO5/c10-2-1-9-3-6(12)8(14)7(13)5(9)4-11/h5-8,10-14H,1-4H2/t5-,6+,7-,8-/m1/s1
InChIKey:
IBAQFPQHRJAVAV-ULAWRXDQSA-N

引用这个纪录

CBID:374 http://www.chembase.cn/molecule-374.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
IUPAC传统名
miglitol
(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
商标名
Glyset
别名
Miglitol
Glyset
N -Hydroxyethyl-1-desoxynojirimycin
Diastabol
Miglitol
(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
CAS号
72432-03-2
MDL号
MFCD00867240
PubChem SID
46504492
160963837
PubChem CID
441314

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 12.901322  质子受体
质子供体 LogD (pH = 5.5) -5.2772155 
LogD (pH = 7.4) -3.6036737  Log P -3.1927972 
摩尔折射率 48.1614 cm3 极化性 19.51395 Å3
极化表面积 104.39 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -2.3  LOG S 0.47 
溶解度 6.10e+02 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
Soluble expand 查看数据来源
疏水性(logP)
-1.256 expand 查看数据来源
-2.7 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
生物活性机理
alpha- and beta-Glucosidase inhibitor expand 查看数据来源
纯度
95% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
应用领域
Antidiabetic used in the management of diabetes mellitus expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals
DrugBank -  DB00491 external link
Item Information
Drug Groups approved
Description Miglitol is an oral anti-diabetic drug that acts by inhibiting the ability of the patient to breakdown complex carbohydrates into glucose. It is primarily used in diabetes mellitus type 2 for establishing greater glycemic control by preventing the digestion of carbohydrates (such as disaccharides, oligosaccharides, and polysaccharides) into monosaccharides which can be absorbed by the body.

Miglitol inhibits glycoside hydrolase enzymes called alpha-glucosidases. Since miglitol works by preventing digestion of carbohydrates, it lowers the degree of postprandial hyperglycemia. It must be taken at the start of main meals to have maximal effect. Its effect will depend on the amount of non-monosaccharide carbohydrates in a person's diet.

In contrast to acarbose (another alpha-glucosidase inhibitor), miglitol is systemically absorbed; however, it is not metabolized and is excreted by the kidneys.
Indication For use as an adjunct to diet to improve glycemic control in patients with non-insulin-dependent diabetes mellitus (NIDDM) whose hyperglycemia cannot be managed with diet alone.
Pharmacology Miglitol, an oral alpha-glucosidase inhibitor, is a desoxynojirimycin derivative that delays the digestion of ingested carbohydrates, thereby resulting in a smaller rise in blood glucose concentration following meals. As a consequence of plasma glucose reduction, miglitol reduce levels of glycosylated hemoglobin in patients with Type II (non-insulin-dependent) diabetes mellitus. Systemic nonenzymatic protein glycosylation, as reflected by levels of glycosylated hemoglobin, is a function of average blood glucose concentration over time. Because its mechanism of action is different, the effect of miglitol to enhance glycemic control is additive to that of sulfonylureas when used in combination. In addition, miglitol diminishes the insulinotropic and weight-increasing effects of sulfonylureas. Miglitol has minor inhibitory activity against lactase and consequently, at the recommended doses, would not be expected to induce lactose intolerance.
Toxicity Unlike sulfonylureas or insulin, an overdose will not result in hypoglycemia. An overdose may result in transient increases in flatulence, diarrhea, and abdomi-nal discomfort. Because of the lack of extra-intestinal effects seen with miglitol, no serious systemic reactions are expected in the event of an overdose.
Affected Organisms
Humans and other mammals
Biotransformation Miglitol is not metabolized in man or in any animal species studied.
Absorption Absorption of miglitol is saturable at high doses with 25 mg being completely absorbed while a 100-mg dose is only 50-70% absorbed. No evidence exists to show that systemic absorption of miglitol adds to its therapeutic effect.
Half Life The elimination half-life of miglitol from plasma is approximately 2 hours.
Protein Binding The protein binding of miglitol is negligible (<4.0%).
Elimination Miglitol is not metabolized in man or in any animal species studied. It is eliminated by renal excretion as an unchanged drug.
Distribution * 0.18 L/kg
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S2589 external link
Research Area: Metabolic Disease
Biological Activity:
Miglitol (Glyset) is an oral anti-diabetic drug that acts by inhibiting the ability of the patient to breakdown complex carbohydrates into glucose. Miglitol (Glyset) is primarily used in diabetes mellitus type 2 for establishing greater glycemic control by preventing the digestion of carbohydrates (such as disaccharides, oligosaccharides, and polysaccharides) into monosaccharides which can be absorbed by the body. [1]References on Miglitol (Glyset)[1] http://en.wikipedia.org/wiki/Miglitol, ,

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Japan. Pat., 1981, 81 83 409; CA, 95, 163893u, (pharmacol)
  • Eur. Pat., 1982, 55 431; CA, 98, 34905n, (synth)
  • Lembcke, B. et al., Digestion, 1985, 31, 109, (pharmacol)
  • Cauderay, M. et al., Metab., Clin. Exp., 1986, 35, 472, (pharmacol)
  • Joubert, P.H. et al., Eur. J. Clin. Pharmacol., 1987, 31, 723, (pharmacol)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 290
  • Ahr, H. et al., Arzneim.-Forsch., 1997, 47, 734
  • Scott, L.J. et al., Drugs, 2000, 59, 521-549
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专利

专利

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