(1S,2S,3R,4S,5S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

• ChemBase编号: 4394
• 分子式: C10H21NO7
• 平均质量: 267.27624
• 单一同位素质量: 267.13180202
• SMILES: O[C@@]1(C[C@H](NC(CO)CO)[C@H](O)[C@@H](O)[C@@H]1O)CO
• Canonical SMILES: OCC(N[C@H]1C[C@](O)(CO)[C@H]([C@@H]([C@H]1O)O)O)CO
• InChI: InChI=1S/C10H21NO7/c12-2-5(3-13)11-6-1-10(18,4-14)9(17)8(16)7(6)15/h5-9,11-18H,1-4H2/t6-,7-,8+,9-,10-/m0/s1
• InChIKey: FZNCGRZWXLXZSZ-CIQUZCHMSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,3R,4S,5S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
• IUPAC传统名: voglibose
• 商标名: Basen (Takeda Chemical Industries); Volix (Ranbaxy labs); Glustat; Vocarb; Basen
• 别名: 3,4-Dideoxy-4-{[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-D-epi-inositol; N-(1,3-Dihydroxyprop-2-yl)valiolamine; Voglibose; voglibose; Voglibose

登记号

• CAS号: 83480-29-9
• MDL号: MFCD00865496
• PubChem SID: 46504462; 160967826
• PubChem CID: 444020

理论计算性质

JChem

• Acid pKa: 12.455839
• 质子受体: 8
• 质子供体: 8
• LogD (pH = 5.5): -6.9796877
• LogD (pH = 7.4): -5.301458
• Log P: -4.8527865
• 摩尔折射率: 59.5467 cm^3
• 极化性: 24.53386 Å^3
• 极化表面积: 153.64 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -2.34
• LOG S: -0.15
• 溶解度: 1.90e+02 g/l

分子性质

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥97.0% (TLC)
• Empirical Formula (Hill Notation): C10H21NO7

详细说明

DrugBank - DB04878

• Drug Groups: approved; investigational
• Description: Voglibose (INN and USAN) is an alpha-glucosidase inhibitor used for lowering post-prandial blood glucose levels in people with diabetes mellitus. It is made in India by Ranbaxy Labs and sold under the trade name Volix. [Wikipedia]
• Indication: For the treatment of diabetes. It is specifically used for lowering post-prandial blood glucose levels thereby reducing the risk of macrovascular complications.
• Pharmacology: Voglibose, an alpha-glucosidase inhibitor, is a synthetic compound with potent and enduring therapeutic efficacies against disorders of sensory, motor and autonomic nerve systems due to diabetes mellitus. The drug was approved in Japan in 1994 for the treatment of diabetes, and it is under further investigation by Takeda for the treatment of impaired glucose tolerance. Alpha-glucosidase inhibitors are oral anti-diabetic drugs used for diabetes mellitus type 2 that work by preventing the digestion of complex carbohydrates (such as starch). Complex carbohydrates are normally converted into simple sugars (monosaccharides) which can be absorbed through the intestine. Hence, alpha-glucosidase inhibitors reduce the impact of complex carbohydrates on blood sugar.
• Affected Organisms: Humans and other mammals
• Biotransformation: Little metabolism occurs and no metabolites have as yet been identified.
• Absorption: Slowly and poorly absorbed
• References: Aso Y, Yamamoto R, Suetsugu M, Matsumoto S, Wakabayashi S, Matsutomo R, Takebayashi K, Inukai T: Comparison of the effects of pioglitazone and voglibose on circulating total and high-molecular-weight adiponectin, and on two fibrinolysis inhibitors, in patients with Type 2 diabetes. Diabet Med. 2007 Sep;24(9):962-8. Epub 2007 May 17. [Pubmed] ; Kurebayashi S, Watada H, Tanaka Y, Kawasumi M, Kawamori R, Hirose T: Efficacy and adverse effects of nateglinide in early type 2 diabetes. Comparison with voglibose in a cross-over study. Endocr J. 2006 Apr;53(2):213-7. [Pubmed] ; Satoh N, Shimatsu A, Yamada K, Aizawa-Abe M, Suganami T, Kuzuya H, Ogawa Y: An alpha-glucosidase inhibitor, voglibose, reduces oxidative stress markers and soluble intercellular adhesion molecule 1 in obese type 2 diabetic patients. Metabolism. 2006 Jun;55(6):786-93. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - 50359

Application
Voglibose is an α-glucosidase inhibitor, similar to acarbose and miglitol, used for lowering post-prandial hyperglycemia (PPHG) in people with diabetes mellitus. Voglibose is used to study it benefits as a protectant against ischemia-reperfusion injury through glucagon-like peptide 1 receptors and the phosphoinositide 3-kinase-Akt-endothelial nitric oxide synthase pathway.

参考文献

• Aso Y, Yamamoto R, Suetsugu M, Matsumoto S, Wakabayashi S, Matsutomo R, Takebayashi K, Inukai T: Comparison of the effects of pioglitazone and voglibose on circulating total and high-molecular-weight adiponectin, and on two fibrinolysis inhibitors, in patients with Type 2 diabetes. Diabet Med. 2007 Sep;24(9):962-8. Epub 2007 May 17. Pubmed
• Kurebayashi S, Watada H, Tanaka Y, Kawasumi M, Kawamori R, Hirose T: Efficacy and adverse effects of nateglinide in early type 2 diabetes. Comparison with voglibose in a cross-over study. Endocr J. 2006 Apr;53(2):213-7. Pubmed
• Satoh N, Shimatsu A, Yamada K, Aizawa-Abe M, Suganami T, Kuzuya H, Ogawa Y: An alpha-glucosidase inhibitor, voglibose, reduces oxidative stress markers and soluble intercellular adhesion molecule 1 in obese type 2 diabetic patients. Metabolism. 2006 Jun;55(6):786-93. Pubmed