Miglitol | CAS#72432-03-2 | alpha-glucosidase inhibitor

MedKoo Cat#: 319604 | Name: Miglitol

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Miglitol, also known as BAY1099; Seibule; Diastabol; Glyset, is an alpha-glucosidase inhibitor. Miglitol is an oral anti-diabetic drug that acts by inhibiting the ability of the patient to break down 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.

Chemical Structure

Miglitol

CAS#72432-03-2

Theoretical Analysis

MedKoo Cat#: 319604

Name: Miglitol

CAS#: 72432-03-2

Chemical Formula: C8H17NO5

Exact Mass: 207.1107

Molecular Weight: 207.23

Elemental Analysis: C, 46.37; H, 8.27; N, 6.76; O, 38.60

Price and Availability

Size	Price	Availability
250mg	USD 250.00	2 weeks
1g	USD 550.00	2 weeks
5g	USD 950.00	2 weeks

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Synonym

BAY-1099; BAY 1099; BAY1099; Seibule; Diastabol; Glyset; Miglitol.

IUPAC/Chemical Name

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

InChi Key

IBAQFPQHRJAVAV-ULAWRXDQSA-N

InChi Code

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

SMILES Code

O[C@H]1[C@@H]([C@H](CN([C@@H]1CO)CCO)O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Miglitol, and other structurally-related iminosugars, inhibit 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.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Miglitol is an oral anti-diabetic drug that acts by inhibiting the ability of the patient to breakdown complex carbohydrates into glucose.

In vitro activity:

The bEnd.3 cells, a microvascular endothelial cell line, were pre-treated with various concentrations of miglitol and then were incubated with H(2)O(2) for 1 - 2 h. Treatment of bEnd.3 cells with miglitol resulted in the protection of cell viability, suppression of mitochondrial superoxide production, and DNA strand breakage under the oxidative stress. Reference: J Pharmacol Sci. 2012;120(2):121-8. https://pubmed.ncbi.nlm.nih.gov/23018899/

In vivo activity:

The non-fasting blood glucose concentrations gradually increased in OLETF (Otsuka Long-Evans Tokushima Fatty) rats fed the control diet and, at week 64, were significantly higher than those in OLETF rats fed the miglitol diet and age-matched Long-Evans Tokushima Otsuka (LETO) rats, which are control, non-diabetic, non-obese rats of the same strain. Furthermore, insulin concentrations after glucose-loading were significantly lower in OLETF rats fed the control diet than in those fed the miglitol diet. Feeding OLETF rats a miglitol diet reduced fibrosis and the loss of beta-cells. Reference: Eur J Pharmacol. 2009 Dec 10;624(1-3):51-7. https://pubmed.ncbi.nlm.nih.gov/19818342/

	Solvent	mg/mL	mM
Solubility
	DMSO	10.9	52.63
	PBS (pH 7.2)	10.0	48.26
	Water	87.2	420.99

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 207.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kim HM, Hyun CG. Miglitol, an Oral Antidiabetic Drug, Downregulates Melanogenesis in B16F10 Melanoma Cells through the PKA, MAPK, and GSK3β/β-Catenin Signaling Pathways. Molecules. 2022 Dec 23;28(1):115. doi: 10.3390/molecules28010115. PMID: 36615308; PMCID: PMC9822252. 2. Aoki C, Suzuki K, Yanagi K, Satoh H, Niitani M, Aso Y. Miglitol, an anti-diabetic drug, inhibits oxidative stress-induced apoptosis and mitochondrial ROS over-production in endothelial cells by enhancement of AMP-activated protein kinase. J Pharmacol Sci. 2012;120(2):121-8. doi: 10.1254/jphs.12108fp. Epub 2012 Sep 26. PMID: 23018899. 3. Fukaya N, Mochizuki K, Tanaka Y, Kumazawa T, Jiuxin Z, Fuchigami M, Goda T. The alpha-glucosidase inhibitor miglitol delays the development of diabetes and dysfunctional insulin secretion in pancreatic beta-cells in OLETF rats. Eur J Pharmacol. 2009 Dec 10;624(1-3):51-7. doi: 10.1016/j.ejphar.2009.09.048. Epub 2009 Oct 7. PMID: 19818342. 4. Hirata A, Igarashi M, Iwai H, Tominaga M. Effect of miglitol, an alpha-glucosidase inhibitor, on atherogenic outcomes in balloon-injured diabetic rats. Horm Metab Res. 2009 Mar;41(3):213-20. doi: 10.1055/s-0028-1105919. Epub 2008 Dec 15. PMID: 19085811.

In vitro protocol:

In vivo protocol:

1. Fukaya N, Mochizuki K, Tanaka Y, Kumazawa T, Jiuxin Z, Fuchigami M, Goda T. The alpha-glucosidase inhibitor miglitol delays the development of diabetes and dysfunctional insulin secretion in pancreatic beta-cells in OLETF rats. Eur J Pharmacol. 2009 Dec 10;624(1-3):51-7. doi: 10.1016/j.ejphar.2009.09.048. Epub 2009 Oct 7. PMID: 19818342. 2. Hirata A, Igarashi M, Iwai H, Tominaga M. Effect of miglitol, an alpha-glucosidase inhibitor, on atherogenic outcomes in balloon-injured diabetic rats. Horm Metab Res. 2009 Mar;41(3):213-20. doi: 10.1055/s-0028-1105919. Epub 2008 Dec 15. PMID: 19085811.

1: Sugimoto S, Nakajima H, Kosaka K, Hosoi H. Review: Miglitol has potential as a therapeutic drug against obesity. Nutr Metab (Lond). 2015 Dec 1;12:51. doi: 10.1186/s12986-015-0048-8. eCollection 2015. Review. PubMed PMID: 26628904; PubMed Central PMCID: PMC4666030. 2: Imai C, Harazaki T, Inoue S, Mochizuki K, Goda T. Treatment with DPP-4I Anagliptin or α-GI Miglitol Reduces IGT Development and the Expression of CVD Risk Factors in OLETF Rats. J Nutr Sci Vitaminol (Tokyo). 2015;61(4):313-21. doi: 10.3177/jnsv.61.313. PubMed PMID: 26440638. 3: Ueno H, Tsuchimochi W, Wang HW, Yamashita E, Tsubouchi C, Nagamine K, Sakoda H, Nakazato M. Effects of Miglitol, Acarbose, and Sitagliptin on Plasma Insulin and Gut Peptides in Type 2 Diabetes Mellitus: A Crossover Study. Diabetes Ther. 2015 Jun;6(2):187-96. doi: 10.1007/s13300-015-0113-3. Epub 2015 Jun 9. PubMed PMID: 26055217; PubMed Central PMCID: PMC4478179. 4: Asamoto H, Nobushi Y, Oi T, Uchikura K. Determination of Miglitol by Column-Switching Ion-Pair HPLC with Tris(2,2'-bipyridine)ruthenium(II)-Electrogenerated Chemiluminescence Detection. Chem Pharm Bull (Tokyo). 2015;63(6):476-80. doi: 10.1248/cpb.c14-00788. PubMed PMID: 26027473. 5: Sasaki T, Hiraga H, Yokota-Hashimoto H, Kitamura T. Miglitol protects against age-dependent weight gain in mice: A potential role of increased UCP1 content in brown adipose tissue. Endocr J. 2015;62(5):469-73. doi: 10.1507/endocrj.EJ15-0116. Epub 2015 Apr 2. PubMed PMID: 25833077. 6: Ezeji GC, Inoue T, Bahtiyar G, Sacerdote A. Hallucinations associated with miglitol use in a patient with chronic kidney disease and hypothyroidism. BMJ Case Rep. 2015 Feb 9;2015. pii: bcr2014207345. doi: 10.1136/bcr-2014-207345. PubMed PMID: 25666246. 7: Kishimoto M, Noda M. Additive effects of miglitol and anagliptin on insulin-treated type 2 diabetes mellitus: a case study. Clin Drug Investig. 2015 Feb;35(2):141-7. doi: 10.1007/s40261-014-0260-8. PubMed PMID: 25511640; PubMed Central PMCID: PMC4300407. 8: Lee EY, Kaneko S, Jutabha P, Zhang X, Seino S, Jomori T, Anzai N, Miki T. Distinct action of the α-glucosidase inhibitor miglitol on SGLT3, enteroendocrine cells, and GLP1 secretion. J Endocrinol. 2015 Mar;224(3):205-14. doi: 10.1530/JOE-14-0555. Epub 2014 Dec 8. PubMed PMID: 25486965; PubMed Central PMCID: PMC4324305. 9: Mikada A, Narita T, Yokoyama H, Yamashita R, Horikawa Y, Tsukiyama K, Yamada Y. Effects of miglitol, sitagliptin, and initial combination therapy with both on plasma incretin responses to a mixed meal and visceral fat in over-weight Japanese patients with type 2 diabetes. "the MASTER randomized, controlled trial". Diabetes Res Clin Pract. 2014 Dec;106(3):538-47. doi: 10.1016/j.diabres.2014.09.040. Epub 2014 Oct 7. PubMed PMID: 25451890. 10: Shirakawa J, Murohashi Y, Okazaki N, Yamazaki S, Tamura T, Okuyama T, Togashi Y, Terauchi Y. Using miglitol at 30 min before meal is effective in hyperinsulinemic hypoglycemia after a total gastrectomy. Endocr J. 2014 Nov 28;61(11):1115-23. Epub 2014 Aug 19. PubMed PMID: 25142087. 11: Hariya N, Mochizuki K, Inoue S, Saito M, Fuchigami M, Goda T, Osonoi T. Switching α-glucosidase inhibitors to miglitol reduced glucose fluctuations and circulating cardiovascular disease risk factors in type 2 diabetic Japanese patients. Drugs R D. 2014 Sep;14(3):177-84. doi: 10.1007/s40268-014-0055-7. PubMed PMID: 25079671; PubMed Central PMCID: PMC4153962. 12: Mizuno-Yasuhira A, Kinoshita K, Jingu S, Yamaguchi J. A sensitive and selective method for the quantitative analysis of miglitol in rat plasma using unique solid-phase extraction coupled with liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2014 Oct;28(10):1423-9. doi: 10.1002/bmc.3185. Epub 2014 Apr 7. PubMed PMID: 24706526. 13: Ihana N, Tsujimoto T, Yamamoto-Honda R, Kishimoto M, Kajio H, Noto H, Kakei M, Noda M. Improvement of both fasting and postprandial glycemic control by the two-step addition of miglitol and mitiglinide to basal insulin therapy: a pilot study. Diabetol Metab Syndr. 2014 Mar 31;6:48. doi: 10.1186/1758-5996-6-48. eCollection 2014. PubMed PMID: 24684803; PubMed Central PMCID: PMC4025538. 14: Sugimoto S, Nakajima H, Kodo K, Mori J, Matsuo K, Kosaka K, Aoi W, Yoshimoto K, Ikegaya H, Hosoi H. Miglitol increases energy expenditure by upregulating uncoupling protein 1 of brown adipose tissue and reduces obesity in dietary-induced obese mice. Nutr Metab (Lond). 2014 Mar 26;11(1):14. doi: 10.1186/1743-7075-11-14. PubMed PMID: 24669882; PubMed Central PMCID: PMC3986880. 15: Imai C, Saito M, Mochizuki K, Fuchigami M, Goda T, Osonoi T. Cotreatment with the α-glucosidase inhibitor miglitol and DPP-4 inhibitor sitagliptin improves glycemic control and reduces the expressions of CVD risk factors in type 2 diabetic Japanese patients. Metabolism. 2014 Jun;63(6):746-53. doi: 10.1016/j.metabol.2013.12.014. Epub 2014 Jan 7. PubMed PMID: 24559582. 16: Aoki K, Kamiyama H, Masuda K, Kamiko K, Noguchi Y, Tajima K, Terauchi Y. Effects of miglitol, vildagliptin, or their combination on serum insulin and peptide YY levels and plasma glucose, cholecystokinin, ghrelin, and obestatin levels. Endocr J. 2014;61(3):249-56. Epub 2013 Dec 27. PubMed PMID: 24389993. 17: Choi HG, Jeon JY, Im YJ, Kim Y, Jang H, Kang S, Kim KH, Chae SW, Lee SY, Kim MG. Pharmacokinetic comparisons between two formulations containing 100 mg of miglitol in healthy male Korean volunteers: a randomized, open-label, single-dose, two-period, two-sequence crossover bioequivalence study. Int J Clin Pharmacol Ther. 2014 Jan;52(1):55-63. doi: 10.5414/CP201994. PubMed PMID: 24290415. 18: Ishibashi K, Hara A, Fujitani Y, Uchida T, Komiya K, Tamaki M, Abe H, Ogihara T, Kanazawa A, Kawamori R, Watada H. Beneficial effects of vildagliptin combined with miglitol on glucose tolerance and islet morphology in diet-controlled db/db mice. Biochem Biophys Res Commun. 2013 Nov 1;440(4):570-5. doi: 10.1016/j.bbrc.2013.09.110. Epub 2013 Oct 5. PubMed PMID: 24103756. 19: Sasaki T, Shimpuku M, Kitazumi T, Hiraga H, Nakagawa Y, Shibata H, Okamatsu-Ogura Y, Kikuchi O, Kim HJ, Fujita Y, Maruyama J, Susanti VY, Yokota-Hashimoto H, Kobayashi M, Saito M, Kitamura T. Miglitol prevents diet-induced obesity by stimulating brown adipose tissue and energy expenditure independent of preventing the digestion of carbohydrates. Endocr J. 2013;60(10):1117-29. Epub 2013 Aug 30. PubMed PMID: 23995917. 20: Kitano D, Chiku M, Li Y, Okumura Y, Fukamachi D, Takayama T, Hiro T, Saito S, Hirayama A. Miglitol improves postprandial endothelial dysfunction in patients with acute coronary syndrome and new-onset postprandial hyperglycemia. Cardiovasc Diabetol. 2013 Jun 19;12:92. doi: 10.1186/1475-2840-12-92. PubMed PMID: 23777506; PubMed Central PMCID: PMC3691582.