Azilsartan
[CAS# 147403-03-0]

Identification

• Classification: Biochemical >> Peptide
• Name: Azilsartan
• Synonyms: 2-Ethoxy-1-[[2'-(4,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid
• Molecular Formula: C₂₅H₂₀N₄O₅
• Molecular Weight: 456.45
• CAS Registry Number: 147403-03-0
• EC Number: 808-058-6
• SMILES: CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NOC(=O)N5)C(=O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.695, Calc.^*

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

Safety Data

• Hazard Symbols: GHS08 Danger
• Risk Statements: H360-H361-H362-H372
• Safety Statements: P203-P260-P263-P264-P270-P280-P318-P319-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	2	H361
Reproductive toxicity	Lact.	-	H362
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Reproductive toxicity	Repr.	1B	H360

Discovery and Applications

Azilsartan is an antihypertensive drug that belongs to the class of angiotensin II receptor antagonists (ARBs). It is used primarily for the treatment of high blood pressure (hypertension) and is marketed under the brand name Edarbi, among others. This medication works by blocking the action of angiotensin II, a hormone that causes blood vessels to constrict, thereby lowering blood pressure. Azilsartan is known for its high specificity and potency in blocking the angiotensin II receptor, making it a highly effective treatment for hypertension.

The discovery of azilsartan dates back to the early 2000s when pharmaceutical companies were exploring new ARBs as alternatives to older drugs in the same class, such as losartan and valsartan. Azilsartan was developed by Takeda Pharmaceutical Company and was introduced to the market in the early 2010s. It is considered one of the more potent ARBs available, with a longer half-life than many of its counterparts, allowing for once-daily dosing, which improves patient adherence to the treatment regimen.

Azilsartan exerts its effects by selectively binding to the AT1 receptor, a subtype of the angiotensin II receptor. Angiotensin II typically binds to this receptor, causing vasoconstriction and an increase in blood pressure. By blocking this receptor, azilsartan prevents the binding of angiotensin II, leading to vasodilation and a subsequent reduction in blood pressure. The mechanism of action of azilsartan is similar to other ARBs, but its higher affinity for the AT1 receptor distinguishes it from other drugs in the same class.

Azilsartan has been shown to be highly effective in reducing systolic and diastolic blood pressure. Clinical trials have demonstrated that it can lower blood pressure significantly, both as a monotherapy and in combination with other antihypertensive drugs, such as calcium channel blockers or diuretics. In addition to its use in hypertension, azilsartan has also been studied for its potential benefits in treating other cardiovascular conditions, including heart failure and chronic kidney disease, though its primary application remains in hypertension management.

One of the advantages of azilsartan over other ARBs is its long duration of action. The drug's long half-life allows for a steady reduction in blood pressure throughout the day, making it particularly convenient for patients who require a once-daily medication. Moreover, azilsartan is well-tolerated by most patients, with a side effect profile similar to that of other ARBs. The most common side effects include dizziness, headache, and fatigue, but serious side effects such as hyperkalemia (elevated potassium levels) and renal dysfunction can occur, especially in patients with pre-existing kidney conditions.

Azilsartan has also been shown to have a relatively low incidence of drug interactions, making it a good option for patients who are on multiple medications. However, as with all antihypertensive drugs, it is essential to monitor blood pressure regularly and adjust the dosage if necessary to ensure optimal therapeutic outcomes. Azilsartan can be used alone or in combination with other antihypertensive agents to provide individualized treatment based on the patient's needs.

In conclusion, azilsartan is an effective and potent medication for the treatment of hypertension. Its ability to block the angiotensin II receptor, its long half-life, and its favorable side effect profile make it a popular choice among healthcare providers for managing high blood pressure. As research continues, azilsartan may find additional uses in treating other cardiovascular and renal conditions, further expanding its therapeutic potential.

References

2025. Beneficial Effects of Angiotensin II Receptor Blockers on Mortality in Patients with COVID-19: A Retrospective Study from 2019 to 2020 in China. Cardiovascular Drugs and Therapy, 39, 1.
DOI: 10.1007/s10557-023-07494-5

2024. A Systematic Literature Review and Network Meta-analysis of Azilsartan Medoxomil Compared to Other Anti-hypertensives Efficacy in Lowering Blood Pressure Amongst Mild to Moderate Hypertensive Patients. Advances in Therapy, 41, 11.
DOI: 10.1007/s12325-024-02997-5

1996. Synthesis and Angiotensin II Receptor Antagonistic Activities of Benzimidazole Derivatives Bearing Acidic Heterocycles as Novel Tetrazole Bioisosteres. Journal of Medicinal Chemistry, 39, 1.
DOI: 10.1021/jm960547h