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72432-03-2, Miglitol, CAS:72432-03-2

72432-03-2, Miglitol,
CAS:72432-03-2
C8H17NO5 / 207.22
MFCD00867240

米格列醇, Miglitol

N-(b-Hydroxyethyl)-1-deoxynojirimycin

Inhibitor of α-glucosidase with applications in diabetes therapy for control of post-prandial blood glucose fluctuations. The compound inhibits the digestive breakdown of complex carbohydrates to absorbable monosaccharides and smoothens hyperglycaemic peaks in type 2 diabetes mellitus. It also possesses anti-obesity effects thanks to activation of brown adipose tissue and increasing energy expenditure.

A potent α-glucosidase inhibitor. A new antidiabetic drug.

Miglitol is a desoxynojirimycin derivative and inhibitor of alpha-glucosidase with antihyperglycemic activity. Miglitol binds to and inhibits alpha-glucosidase, an enteric enzyme found in the brush border of the small intestines that hydrolyzes oligosaccharides and disaccharides into glucose and other monosaccharides. This prevents the breakdown of larger carbohydrates into glucose and decreases the rise in postprandial blood glucose levels. Compared to acarbose, miglitol is systemically absorbed.

Miglitol is an alpha-glucosidase inhibitor which decreases intestinal absorption of carbohydrates and is used as an adjunctive therapy in the management of type 2 diabetes. Miglitol has not been linked to instances of clinically apparent acute liver injury.

Miglitol, also known as glyset or bay m 1099, belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. Miglitol is a drug which is used 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. Miglitol exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Miglitol has been detected in multiple biofluids, such as urine and blood. Within the cell, miglitol is primarily located in the cytoplasm.

Title: Miglitol

CAS Registry Number: 72432-03-2

CAS Name: 1,5-Dideoxy-1,5-[(2-hydroxyethyl)imino]-D-glucitol

Additional Names: N-(2-hydroxyethyl)moranoline; (2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)-3,4,5-piperidinetriol; N-(b-hydroxyethyl)-1-deoxynojirimycin

Manufacturers' Codes: Bay m 1099

Trademarks: Diastabol (Sanofi-Synthelabo); Glyset (Pfizer)

Molecular Formula: C8H17NO5

Molecular Weight: 207.22

Percent Composition: C 46.37%, H 8.27%, N 6.76%, O 38.60%

Literature References: a-Glucosidase inhibitor; hydroxyethyl derivative of 1-deoxynojirimycin, q.v. Prepn: B. Junge et al., DE 2758025; eidem, US 4639436 (1979, 1987 both to Bayer AG). Inhibition of a-glucosidase: B. Lembcke et al., Digestion 31, 120 (1985); and hypoglycemic activity: Y. Yoshikuni et al., J. Pharmacobio-Dyn. 11, 356 (1988). Clinical evaluations in insulin dependent diabetes: J. Gerard et al., Int. J. Clin. Pharmacol. Ther. Toxicol. 25, 483 (1987); F. P. Kennedy, J. E. Gerich, Clin. Pharmacol. Ther. 42, 455 (1987). Review of pharmacology, clinical efficacy, and therapeutic potential in non-insulin dependent diabetes: L. J. Scott, C. M. Spencer, Drugs 59, 521-549 (2000).

Properties: Crystals from ethanol, mp 114°. Sol in water. pKa 5.9.

Melting point: mp 114°

pKa: pKa 5.9

Therap-Cat: Antidiabetic.

Keywords: Antidiabetic; a-Glucosidase Inhibitor.

CAS Number72432-03-2
Product NameMiglitol
IUPAC Name(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
Molecular FormulaC8H17NO5
Molecular Weight207.22 g/mol
InChIInChI=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
InChI KeyIBAQFPQHRJAVAV-ULAWRXDQSA-N
SMILESC1C(C(C(C(N1CCO)CO)O)O)O
SolubilitySoluble
Soluble in water
6.10e+02 g/L
SynonymsBAY m 1099, BAY-m 1099, BAY-m-1099, Diastabol, Glyset, miglitol, miglitol, 4-methylbenzenesulfonate salt, ((D)-isomer), N-hydroxyethyl-1-desoxy-nojirimycin, N-hydroxyethyl-1-desoxynojirimycin, Plumarol
Canonical SMILESC1C(C(C(C(N1CCO)CO)O)O)O
Isomeric SMILESC1[C@@H]([C@H]([C@@H]([C@H](N1CCO)CO)O)O)O
CAS No: 72432-03-2 Synonyms: MiglitolGlyset MDL No: MFCD00867240 Chemical Formula: C8H17NO5 Molecular Weight: 207.22
References: 1. Lembcke B, et.al., Digestion, 1985, 31, p1202. Yoshikuni Y, et.al., J. Pharmacolbio-Dyn., 1988, 11, p356


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