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Azilsartan medoxomil monopotassium (TAK-491; TAK491; Edarbi), the monopotassium salt of Azilsartan medoxomil which is a prodrug of azilsartan, is an angiotensin II receptor (AT1) type 1 antagonist approved as an anti-hypertensive medication to lower blood pressure.
Physicochemical Properties
| Molecular Formula | C₃₀H₂₃KN₄O₈ |
| Molecular Weight | 606.62 |
| Exact Mass | 606.12 |
| Elemental Analysis | C, 59.40; H, 3.82; K, 6.45; N, 9.24; O, 21.10 |
| CAS # | 863031-24-7 |
| Related CAS # | Azilsartan medoxomil; 863031-21-4; Azilsartan; 147403-03-0; Azilsartan-d5; 1346599-45-8 |
| PubChem CID | 23699544 |
| Appearance | White to off-white solid powder |
| LogP | 4.705 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 10 |
| Heavy Atom Count | 43 |
| Complexity | 1110 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | [K].O=C1OC(COC(C2C3=C(N=C(N3CC3C=CC(C4C(C5NC(=O)ON=5)=CC=CC=4)=CC=3)OCC)C=CC=2)=O)=C(C)O1 |
| InChi Key | IHWFKDWIUSZLCJ-UHFFFAOYSA-M |
| InChi Code | InChI=1S/C30H24N4O8.K/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);/q;+1/p-1 |
| Chemical Name | potassium;(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-1-oxa-2-aza-4-azanidacyclopent-2-en-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate |
| Synonyms | TAK-491 monopotassium; Azilsartan kamedoxomil; TAK491 monopotassium |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | AT1 Receptor (IC50 = 2.6 nM ) |
| References |
[1]. Molecular and cellular effects of azilsartan: a new generation angiotensin II receptor blocker. J Hypertens. 2011 Dec;29(12):2476-83. [2]. Antihypertensive, insulin-sensitising and renoprotective effects of a novel, potent and long-acting angiotensin II type 1 receptor blocker, azilsartan medoxomil, in rat and dog models. [3]. Azilsartan medoxomil: a review of its use in hypertension. Clin Drug Investig. 2012 Sep 1;32(9):621-39. [4]. Azilsartan medoxomil/chlorthalidone: a new fixed-dose combination antihypertensive. Ann Pharmacother. 2013 May;47(5):694-703. [5]. The angiotensin receptor blocker, azilsartan medoxomil (TAK-491), suppresses vascular wall expression of plasminogen activator inhibitor type-I protein potentially facilitating the stabilization of atherosclerotic plaques. J Cardiovasc Pharmacol. 2011 Aug;58(2):143-8. [6]. Additive effect of TAK-491, a new angiotensin receptor blocker, and pioglitazone, in reducing myocardial infarct size. Cardiovasc Drugs Ther. 2010 Apr;24(2):107-20. |
| Additional Infomation |
Azilsartan kamedoxomil is an organic potassium salt that is the monopotassium salt of azilsartan medoxomil. A prodrug for azilsartan, it is used for treatment of hypertension. It has a role as a prodrug, an antihypertensive agent and an angiotensin receptor antagonist. It contains an azilsartan medoxomil(1-). See also: Azilsartan (has active moiety); Azilsartan kamedoxomil; chlorthalidone (component of). |
Solubility Data
| Solubility (In Vitro) | DMSO: 114~125 mg/mL (200.5~219.9 mM) |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.6485 mL | 8.2424 mL | 16.4848 mL | |
| 5 mM | 0.3297 mL | 1.6485 mL | 3.2970 mL | |
| 10 mM | 0.1648 mL | 0.8242 mL | 1.6485 mL |