(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol

• ChemBase ID: 374
• Molecular Formular: C8H17NO5
• Molecular Mass: 207.22428
• Monoisotopic Mass: 207.11067265
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
• IUPAC Traditional name: miglitol; (2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
• Brand Name: Glyset
• Synonyms: Miglitol; Glyset; N -Hydroxyethyl-1-desoxynojirimycin; Diastabol; Miglitol; (2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol

Database IDs

• CAS Number: 72432-03-2
• MDL Number: MFCD00867240
• PubChem SID: 46504492; 160963837
• PubChem CID: 441314

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.901322
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -5.2772155
• LogD (pH = 7.4): -3.6036737
• Log P: -3.1927972
• Molar Refractivity: 48.1614 cm^3
• Polarizability: 19.51395 Å^3
• Polar Surface Area: 104.39 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.3
• LOG S: 0.47
• Solubility (Water): 6.10e+02 g/l

PROPERTIES

Physical Property

• Solubility: Soluble
• Hydrophobicity(logP): -1.256; -2.7

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Mechanism of Action: alpha- and beta-Glucosidase inhibitor

Product Information

• Purity: 95%
• Salt Data: Free Base
• Application(s): Antidiabetic used in the management of diabetes mellitus

DETAILS

DrugBank - DB00491

• 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

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, ,

REFERENCES

• 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