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56180-94-0 分子结构
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(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-{[(1S,4S,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol

ChemBase编号:169
分子式:C25H43NO18
平均质量:645.60482
单一同位素质量:645.24801354
SMILES和InChIs

SMILES:
[C@H]1([C@H](O[C@@H]([C@@H]([C@H]1O)O)O[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)O)CO)CO)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C)N[C@H]1C=C([C@@H]([C@@H]([C@H]1O)O)O)CO)O)O
Canonical SMILES:
OC[C@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O[C@H]1O[C@H](C)[C@H]([C@@H]([C@H]1O)O)N[C@H]1C=C(CO)[C@@H]([C@@H]([C@H]1O)O)O)O)O
InChI:
InChI=1S/C25H43NO18/c1-6-11(26-8-2-7(3-27)12(30)15(33)13(8)31)14(32)19(37)24(40-6)43-22-10(5-29)42-25(20(38)17(22)35)44-21-9(4-28)41-23(39)18(36)16(21)34/h2,6,8-39H,3-5H2,1H3/t6-,8+,9-,10-,11-,12+,13+,14+,15+,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-/m1/s1
InChIKey:
XUFXOAAUWZOOIT-JMPDRRIHSA-N

引用这个纪录

CBID:169 http://www.chembase.cn/molecule-169.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,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-{[(1S,4S,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol
IUPAC传统名
acarbose
商标名
Precose
Glucobay
Prandase
别名
Acarbose
CAS号
56180-94-0
PubChem SID
46508248
160963632
PubChem CID
441184

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00284 external link
PubChem 441184 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 11.225573  质子受体 19 
质子供体 14  LogD (pH = 5.5) -9.150389 
LogD (pH = 7.4) -7.7692995  Log P -7.6145587 
摩尔折射率 137.6024 cm3 极化性 57.392616 Å3
极化表面积 321.17 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P -2.66  LOG S -0.64 
溶解度 1.48e+02 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
疏水性(logP)
-6.8 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00284 external link
Item Information
Drug Groups approved; investigational
Description An inhibitor of alpha glucosidase that retards the digestion and absorption of carbohydrates in the small intestine and hence reduces the increase in blood-glucose concentrations after a carbohydrate load. It is given orally to non-insulin dependent diabetes mellitus patients where diet modification or oral hypoglycemic agents do not control their condition. (From Martindale The Extra Pharmacopoeia, 31st ed)
Indication For treatment and management of diabetes type II (used in combination therapy as a second or third line agent)
Pharmacology Used to reduce blood gluose in patients with type 2 diabetes. Acarbose is a complex oligosaccharide that delays the digestion of ingested carbohydrates, thereby resulting in a smaller rise in blood glucose concentration following meals. Acarbose binds to and inhibits alpha amylase and alpha-gluocside hydrolases. In diabetic patients, this enzyme inhibition results in a delayed glucose absorption and a lowering of postprandial hyperglycemia.
Affected Organisms
Humans and other mammals
Absorption Extremely low bioavailability.
Half Life 2 hours
Elimination The fraction of acarbose that is absorbed as intact drug is almost completely excreted by the kidneys.
References
Clissold SP, Edwards C: Acarbose. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential. Drugs. 1988 Mar;35(3):214-43. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Clissold SP, Edwards C: Acarbose. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential. Drugs. 1988 Mar;35(3):214-43. Pubmed
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专利

专利

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