Bexagliflozin
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Product Description
Bexagliflozin is a sodium-glucose cotransporter 2 (SGLT2) inhibitor used primarily to improve glycemic control in adults with type 2 diabetes mellitus. It works by inhibiting the reabsorption of glucose in the kidneys, leading to increased glucose excretion in urine, independent of insulin. This mechanism helps lower blood sugar levels. Bexagliflozin is marketed under the brand name Brenzavvy and is used as an adjunct to diet and exercise. It contains a glucitol ring that mimics glucose, allowing it to bind to the SGLT2 protein, and features an aryl chloride, ether linkage, and benzyl link. The molecule has multiple chiral centers, which are critical for its biological activity. Common side effects include vaginal yeast infections, urinary tract infections, and increased urination, while serious risks include diabetic ketoacidosis, lower limb amputation, dehydration, Fournier's gangrene, and hypoglycemia. Patients should discuss risks and benefits with their healthcare provider and follow instructions carefully.
Note: Bexagliflozin produced by our company is a chemical raw material and is only used for scientific research and production. It cannot be used directly as a drug.
Synthesis Methods
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Synthesis: Bexagliflozin is synthesized through a series of chemical reactions. The process involves the creation of intermediate compounds and the use of specific reagents and solvents. The final product is obtained through purification steps such as high-performance liquid chromatography (HPLC).
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Patent Information: Detailed synthesis methods are described in patent documents such as US7838499B2.
Uses
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Primary Use: Bexagliflozin is primarily used for the treatment of type 2 diabetes mellitus (T2DM) as an adjunct to diet and exercise to improve glycemic control.
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Potential New Uses: Preliminary studies suggest additional therapeutic benefits, particularly in the treatment of hypertension and cardiac arrhythmias. Investigations are ongoing for its potential use in chronic kidney disease in children and sleep apnea.
Mechanism of Action
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SGLT2 Inhibition: Bexagliflozin is a highly specific and potent inhibitor of sodium-glucose co-transporter 2 (SGLT2), which is responsible for 60% to 90% of renal glucose re-uptake. By inhibiting SGLT2, it reduces renal reabsorption of filtered glucose and increases urinary glucose excretion, thereby lowering blood glucose levels independently of insulin sensitivity.
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Additional Effects: Bexagliflozin also exhibits antihypertensive effects and may contribute to weight loss. It has a high selectivity for SGLT2 over SGLT1, which is advantageous in the treatment of hyperglycemia.
Pharmacokinetics
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Absorption: Bexagliflozin is rapidly absorbed from the gastrointestinal tract.
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Distribution: It has a high volume of distribution (262 L) and is 93% protein-bound.
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Metabolism: The primary metabolic pathways involve glucuronidation via UGT1A9 and oxidation via CYP3A4.
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Excretion: Approximately 51.1% of the dose is excreted in feces (28.7% as the parent compound) and 40.5% in urine (1.5% as the parent compound).
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Half-Life: The apparent terminal elimination half-life is approximately 12 hours.
Properties
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Molecular Formula: C₂₄H₂₉ClO₇
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Molecular Weight: 464.94 g/mol
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CAS Registry Number: 1118567-05-7
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IUPAC Name: (2S,3R,4R,5S,6R)-2-(4-chloro-3-{[4-(2-cyclopropoxyethoxy)phenyl]methyl}phenyl)-6-(hydroxymethyl)oxane-3,4,5-triol
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Solubility: Slightly soluble in water (0.0565 mg/mL), soluble in acetone, ethylene glycol, methanol, and propylene glycol
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Partition Coefficient (log P): 2.33
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Acid Dissociation Constant (pKa): 12.57
Safety and Efficacy
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Clinical Trials: Bexagliflozin has been shown to reduce hemoglobin A1c by approximately 0.5%, with similar reductions in systolic blood pressure and body weight compared to other SGLT2 inhibitors.
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Adverse Effects: Common side effects include genital mycotic infections, urinary tract infections, and increased urination. There is also a warning for an increased risk of lower extremity amputation, similar to canagliflozin.
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Cost: Bexagliflozin is suggested to be competitively priced, which may create a temporary niche in the market pending generic availability of other SGLT2 inhibitors.
Regulatory Approval
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FDA Approval: Bexagliflozin was approved by the FDA in January 2023 for the treatment of adults with type 2 diabetes mellitus.
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Indications: It is indicated for use in adults with T2DM but is not recommended for patients with type 1 diabetes due to the risk of diabetic ketoacidosis.