Acarbose
[CAS# 56180-94-0]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Pancreatic hormones and other blood sugar regulating drugs
• Name: Acarbose
• Synonyms: Acarbose; Glucobay; (3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,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
• Molecular Formula: C₂₅H₄₃NO₁₈
• Molecular Weight: 645.61
• CAS Registry Number: 56180-94-0
• EC Number: 260-030-7
• SMILES: C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H](OC([C@@H]([C@H]3O)O)O)CO)CO)O)O)N[C@H]4C=C([C@H]([C@@H]([C@H]4O)O)O)CO

Properties

• Solubility: 129 mg/Ml (DMSO), 129 mg/mL (water) (Expl.)
• Density: 1.7±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.689, Calc.^*
• Boiling Point: 971.6±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 541.4±34.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Acarbose is a complex oligosaccharide and potent anti-diabetic medication known for its ability to inhibit enzymes that break down carbohydrates, thereby slowing glucose absorption in the intestines. Acarbose was initially discovered in the 1970s by researchers exploring potential therapies for diabetes, particularly Type 2 diabetes, a chronic condition marked by high blood glucose levels. This compound was isolated from Actinoplanes sp., a bacterium known for producing various bioactive substances. The discovery of acarbose as an effective alpha-glucosidase inhibitor was a breakthrough in diabetes treatment, as it provided a new approach for managing postprandial (post-meal) blood sugar levels without directly impacting insulin.

Acarbose’s structure, as an oligosaccharide, resembles natural sugars, allowing it to bind to intestinal enzymes such as alpha-amylase and alpha-glucosidase. By inhibiting these enzymes, acarbose effectively delays the conversion of complex carbohydrates into glucose, resulting in slower glucose absorption and reduced postprandial blood glucose spikes. This mechanism makes it particularly useful for Type 2 diabetes patients who benefit from controlled blood glucose levels to prevent complications related to diabetes.

The use of acarbose as an oral antidiabetic agent has been widely accepted, particularly in patients who have difficulty managing blood sugar levels solely through diet and exercise. As a non-systemic medication, acarbose acts locally within the gastrointestinal tract without significant absorption into the bloodstream, making it a low-risk option for many patients. It is often prescribed as an adjunct to other diabetes treatments or lifestyle modifications, providing a complementary mechanism of action that aids in overall blood glucose management.

Beyond its primary use for diabetes, acarbose has also been studied for potential applications in weight management. By delaying carbohydrate digestion, it contributes to reduced calorie absorption and helps regulate body weight, which is beneficial for overweight individuals or those with obesity-related health risks. While not its primary use, this effect has been explored as a possible added benefit of acarbose for individuals with metabolic syndrome or prediabetes.

In recent research, acarbose has garnered interest for its potential effects on gut microbiota and overall metabolic health. The undigested carbohydrates resulting from acarbose activity reach the colon, where they may serve as substrates for fermentation by gut bacteria. This process potentially alters the composition of the microbiota, which may impact metabolic functions and the immune response, opening new avenues for research into acarbose’s broader health benefits.

Overall, acarbose remains a valuable drug in the management of Type 2 diabetes due to its targeted action on carbohydrate digestion and minimal systemic absorption. Its ability to modulate postprandial glucose spikes, combined with ongoing research into its secondary benefits, underscores its importance in metabolic health management.

References

2024. Acarbose ameliorates type 2 diabetes-associated NAFLD and hepatic mitochondrial dysfunction in rats. Scientific Reports, 14(1).
DOI: 10.1038/s41598-024-62684-x

2003. Acarbose: a review of its therapeutic potential in type 2 diabetes mellitus. Drugs, 63(10).
DOI: 10.2165/00003495-200363100-00002

1998. Acarbose-induced acute hepatitis: a case report. American Journal of Gastroenterology, 93(3).
DOI: 10.1111/j.1572-0241.1998.481_1.x