Azilsartan Medoxomil (TAK 491)

Alias: TAK-491; TAK 491; TAK491; Azilsartan medoxomil; Azilsartan medoxomil potassium; trade name: Edarbi. Ipreziv.
Cat No.:V1793 Purity: ≥98%
Azilsartan Medoxomil (formerly also known as TAK-491), the ester prodrugof Azilsartan (TAK-536),is a potent andorally bioavailable angiotensin II type 1 (AT1) receptor antagonist, inhibits the RAAS, with an IC50 of 2.6 nM.
Azilsartan Medoxomil (TAK 491) Chemical Structure CAS No.: 863031-21-4
Product category: RAAS
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
25mg
50mg
100mg
250mg
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1g
Other Sizes

Other Forms of Azilsartan Medoxomil (TAK 491):

  • Azilsartan (TAK-536)
  • Azilsartan D5
  • Azilsartan medoxomil monopotassium (TAK 491)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Azilsartan Medoxomil (formerly also known as TAK-491), the ester prodrug of Azilsartan (TAK-536), is a potent and orally bioavailable angiotensin II type 1 (AT1) receptor antagonist, inhibits the RAAS, with an IC50 of 2.6 nM. It is used for the treatment of hypertension. Azilsartan lowers blood pressure by blocking the action of angiotensin II. Azilsartan also inhibits the accumulation of AII-induced inositol 1-phosphate (IP1) in the cell-based assay with an IC50 value of 9.2 nM. Azilsartan medoxomil is a useful and attractive new option for lowering BP in patients with essential hypertension, particularly for those not able to tolerate other antihypertensive drugs.

Biological Activity I Assay Protocols (From Reference)
ln Vitro

In vitro activity: Azilsartan medoxomil is a prodrug, which is rapidly converted to the active moiety, azilsartan (TAK-536), by ester hydrolysis in the gut and plasma during absorption after oral administration. Azilsartan selectively blocks the binding of angiotensin II to the AT1 (angiotensin II type 1) receptors found in the vascular smooth muscle and the adrenal gland, thereby promoting vasodilation and a decrease in the effects of aldosterone. Azilsartan is a highly selective antagonist to the AT1 receptor, with an IC50 of 2.6 nM, exhibiting a >10,000-fold affinity for the AT1 receptor compared with the AT2 receptor, and has not shown affinity for other cardiac receptors or ion channels. The inhibitory effect of Azilsartan persists after washout of the free compound (IC50 value of 7.4 nM). Azilsartan also inhibits the accumulation of angiotensin II -induced inositol 1-phosphate (IP1) in the cell-based assay with an IC50 value of 9.2 nM, and this effect is resistant to washout (IC50 value of 81.3 nM).


Kinase Assay: A radioligand binding assay is performed by using human AT1 receptor-coated microplates containing 4.4 to 6.2 fmol of receptors/well (10 μg of membrane protein/well). Membrane-coated wells are incubated with 45 μl of assay buffer (50 mM Tris-HCl, 5 mM MgCl2, 1 mM EDTA, and 0.005% CHAPS, pH 7.4) containing various concentrations of test compounds at room temperature. After 90 min, 5 μl of 125I-Sar1-Ile8-AII (final concentration 0.6 nM) dissolved in assay buffer is added to the wells, and the plate is incubated for 5 h. In each step, the plate is briefly and gently shaken on a plate shaker.


Cell Assay: Measurement of Inositol 1-Phosphate Accumulation. Twentyfour hours after transfections with human AT1-expressing plasmids, the cells are starved by changing the culture medium to starvation buffer (1 mM CaCl2, 0.5 mM MgCl2, 4.2 mM KCl, 146 mM NaCl, 5.5 mM glucose, and 10 mM HEPES, pH 7.3). Then, 5 μl/well of the test compounds dissolved in starvation buffer is added to the cells at the indicated concentrations, and they are pretreated for the indicated times. Two hours after starvation, LiCl is added to a final concentration of 50 mM with or without angiotensin II 10 nM, and the cells are further incubated for the indicated times at 37°C. In washout experiments, the cells are washed once with 100 μl/well of starvation buffer to remove unbound compounds before stimulation with angiotensin II. The accumulation of inositol 1-phosphate (IP1) is measured by using a IP-One Tb kit. The fluorescence resonance energy transfer signal is measured on a plate reader.

ln Vivo
In Koletsky rats, Azilsartan treatment lowers blood pressure, basal plasma insulin concentration and the homeostasis model assessment of insulin resistance index, and inhibited over-increase of plasma glucose and insulin concentrations during oral glucose tolerance test. Azilsartan downregulates 11β-hydroxysteroid dehydrogenase type 1 expression.
Animal Protocol
Suspended in 5% Gum Arabic; 1, 2, and 3 mg/kg; Oral gavage
Male Wistar-Kyoto (WKY) rats, obese Koletsky (fak/fak) rats
References
J Pharmacol Exp Ther.2011 Mar;336(3):801-8;Am J Hypertens.2007 May;20(5):579-86.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H24N4O8
Molecular Weight
568.53
CAS #
863031-21-4
SMILES
O=C(C1=C2C(N=C(OCC)N2CC3=CC=C(C4=CC=CC=C4C5=NC(ON5)=O)C=C3)=CC=C1)OCC6=C(C)OC(O6)=O
InChi Key
QJFSABGVXDWMIW-UHFFFAOYSA-N
InChi Code
InChI=1S/C30H24N4O8/c1-3-38-28-31-23-10-6-9-22(27(35)39-16-24-17(2)40-30(37)41-24)25(23)34(28)15-18-11-13-19(14-12-18)20-7-4-5-8-21(20)26-32-29(36)42-33-26/h4-14H,3,15-16H2,1-2H3,(H,32,33,36)
Chemical Name
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-1-((2-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
Synonyms
TAK-491; TAK 491; TAK491; Azilsartan medoxomil; Azilsartan medoxomil potassium; trade name: Edarbi. Ipreziv.
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 114 mg/mL (200.5 mM)
Water:<1 mg/mL
Ethanol:<1 mg/mL
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.7589 mL 8.7946 mL 17.5892 mL
5 mM 0.3518 mL 1.7589 mL 3.5178 mL
10 mM 0.1759 mL 0.8795 mL 1.7589 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

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