Azilsartan free acid
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MedKoo CAT#: 319526

CAS#: 147403-03-0 (free acid)

Description: Azilsartan is an angiotensin II receptor antagonist used in the treatment of hypertension, developed by Takeda. It is marketed in tablet form under the trade name Edarbi as the prodrug azilsartan medoxomil (INN, codenamed TAK-491). Azilsartan medoxomil lowers blood pressure by blocking the action of angiotensin II, a vasopressor hormone.


Chemical Structure

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Azilsartan free acid
CAS# 147403-03-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 319526
Name: Azilsartan free acid
CAS#: 147403-03-0 (free acid)
Chemical Formula: C25H20N4O5
Exact Mass: 456.14337
Molecular Weight: 456.46
Elemental Analysis: C, 65.78; H, 4.42; N, 12.27; O, 17.53

Size Price Shipping out time Quantity
2g USD 250 2 Weeks
5g USD 450 2 Weeks
10g USD 750 2 Weeks
50g USD 1650 2 Weeks
100g USD 2650 2 Weeks
500g USD 3950 2 Weeks
1kg USD 6450 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-08. Prices are subject to change without notice.

Azilsartan free acid, purity > 98%,purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Related CAS #: 1824707-75-6 (trimethylethanolamine)   147403-03-0 (free acid)    

Synonym: TAK-536; TAK-536; TAK-536; Azilsartan; Azilsartan free base

IUPAC/Chemical Name: 2-Ethoxy-1-[[2'-(4,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid

InChi Key: KGSXMPPBFPAXLY-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H20N4O5/c1-2-33-24-26-20-9-5-8-19(23(30)31)21(20)29(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-27-25(32)34-28-22/h3-13H,2,14H2,1H3,(H,30,31)(H,27,28,32)

SMILES Code: O=C(C1=C2C(N=C(OCC)N2CC(C=C3)=CC=C3C4=CC=CC=C4C5=NOC(N5)=O)=CC=C1)O

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 456.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Naruse M, Koike Y, Kamei N, Sakamoto R, Yambe Y, Arimitsu M. Effects of azilsartan compared with telmisartan on insulin resistance in patients with essential hypertension and type 2 diabetes mellitus: An open-label, randomized clinical trial. PLoS One. 2019 Apr 3;14(4):e0214727. doi: 10.1371/journal.pone.0214727. eCollection 2019. PubMed PMID: 30943275; PubMed Central PMCID: PMC6447197.

2: Fukuda M, Isobe-Sasaki Y, Sato R, Miura T, Mizuno M, Ono M, Kiyono K, Yamamoto Y, Hayano J, Ohte N. The angiotensin II type 1 receptor blocker azilsartan can overwhelm the sympathetic nerve activation stimulated by coadministration of calcium channel blockers. J Renin Angiotensin Aldosterone Syst. 2019 Jan-Mar;20(1):1470320319839525. doi: 10.1177/1470320319839525. PubMed PMID: 30915878; PubMed Central PMCID: PMC6437324.

3: Li N, Fan L, Wu B, Dai G, Jiang C, Guo Y, Wang D. Preparation and in vitro/in vivo evaluation of azilsartan osmotic pump tablets based on the preformulation investigation. Drug Dev Ind Pharm. 2019 Mar 25:1-10. doi: 10.1080/03639045.2019.1593441. [Epub ahead of print] PubMed PMID: 30909753.

4: Hardin MD, Jacobs TF. Azilsartan. 2019 Mar 31. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2019 Jan-. Available from http://www.ncbi.nlm.nih.gov/books/NBK538473/ PubMed PMID: 30860708.

5: Ehlken B, Shlaen M, Lopez Fuensalida de Torres MDP, Hisada M, Bennett D. Use of azilsartan medoxomil in the primary-care setting in Germany: A real-world evidence study
. Int J Clin Pharmacol Ther. 2019 Mar 8. doi: 10.5414/CP203359. [Epub ahead of print] PubMed PMID: 30848243.

6: Miyoshi T, Onoue G, Ito H. Effect of Switching to Azilsartan From Fixed-Dose Combination of an Angiotensin II Receptor Blocker and Calcium Channel Blocker or a Thiazide in Patients With Hypertension. J Clin Med Res. 2019 Mar;11(3):202-207. doi: 10.14740/jocmr3723. Epub 2019 Feb 13. PubMed PMID: 30834043; PubMed Central PMCID: PMC6396784.

7: He Y, Zhang W, Guo T, Zhang G, Qin W, Zhang L, Wang C, Zhu W, Yang M, Hu X, Singh V, Wu L, Gref R, Zhang J. Drug nanoclusters formed in confined nano-cages of CD-MOF: dramatic enhancement of solubility and bioavailability of azilsartan. Acta Pharm Sin B. 2019 Jan;9(1):97-106. doi: 10.1016/j.apsb.2018.09.003. Epub 2018 Sep 7. PubMed PMID: 30766781; PubMed Central PMCID: PMC6361728.

8: Matsuo Y, Suematsu Y, Tomita S, Tashiro K, Kuwano T, Kitajima K, Miura SI. Unique mode of binding between angiotensin II type 1 receptor and its blockers. Clin Exp Hypertens. 2018 Nov 19:1-6. doi: 10.1080/10641963.2018.1545851. [Epub ahead of print] PubMed PMID: 30453795.

9: Hussein LA, Magdy NN, Ibrahim MA. Stability-Indicating RP-UPLC Method for Simultaneous Determination of Azilsartan Medoxomil and Chlorthalidone in Tablets in the Presence of Its Degradation Products. J Chromatogr Sci. 2019 Mar 1;57(3):213-219. doi: 10.1093/chromsci/bmy102. PubMed PMID: 30395199.

10: Li Y, Zhu H, Yang J, Ke K, Zhu Y, Chen L, Qu Y, Suo R, Chen X, Zhu Y. Discovering Proangiogenic Drugs in Ischemic Stroke Based on the Relationship between Protein Domain and Drug Substructure. ACS Chem Neurosci. 2019 Jan 16;10(1):507-517. doi: 10.1021/acschemneuro.8b00381. Epub 2018 Oct 29. PubMed PMID: 30346717.

11: Collier DJ, Juhasz A, Agabiti-Rosei E, Lloyd E, Hisada M, Zhao L, Kupfer S, Caulfield MJ. Efficacy and safety of azilsartan medoxomil/chlortalidone fixed-dose combination in hypertensive patients uncontrolled on azilsartan medoxomil alone: A randomized trial. J Clin Hypertens (Greenwich). 2018 Oct;20(10):1473-1484. doi: 10.1111/jch.13376. Epub 2018 Oct 9. PubMed PMID: 30302936.

12: Ferdinand KC, Bakris GL, Cushman WC, Weber MA, Lloyd E, Wu J, White WB. Comparison of Effectiveness of Azilsartan Medoxomil and Olmesartan in Blacks Versus Whites With Systemic Hypertension. Am J Cardiol. 2018 Nov 1;122(9):1496-1505. doi: 10.1016/j.amjcard.2018.07.022. Epub 2018 Aug 4. PubMed PMID: 30217371.

13: Komaki H, Iwasa M, Hayakawa Y, Okamoto C, Minatoguchi S, Yamada Y, Kanamori H, Kawasaki M, Nishigaki K, Minatoguchi S. Azilsartan attenuates cardiac damage caused by high salt intake through the downregulation of the cardiac (pro)renin receptor and its downstream signals in spontaneously hypertensive rats. Hypertens Res. 2018 Nov;41(11):886-896. doi: 10.1038/s41440-018-0099-0. Epub 2018 Sep 12. PubMed PMID: 30209283.

14: Weber MA, Sever P, Juhasz A, Roberts A, Cao C. A randomized trial of the efficacy and safety of azilsartan medoxomil combined with chlorthalidone. J Renin Angiotensin Aldosterone Syst. 2018 Jul-Sep;19(3):1470320318795000. doi: 10.1177/1470320318795000. PubMed PMID: 30175930; PubMed Central PMCID: PMC6122257.

15: Mishra S, Ingole S, Jain R. Salt sensitivity and its implication in clinical practice. Indian Heart J. 2018 Jul - Aug;70(4):556-564. doi: 10.1016/j.ihj.2017.10.006. Epub 2017 Oct 10. Review. PubMed PMID: 30170653; PubMed Central PMCID: PMC6116721.

16: Grigoreva NY, Koroleva ME. [Choice of an Optimal Blocker of the Renin-Angiotensin-Aldosterone System in Patients With Concomitant Arterial Hypertension and Chronic Obstructive Pulmonary Disease]. Kardiologiia. 2018 Aug;(8):50-57. Russian. PubMed PMID: 30131042.

17: Mahmood NMA, Hussain SA, Mirza RR. Azilsartan improves the effects of etanercept in patients with active rheumatoid arthritis: a pilot study. Ther Clin Risk Manag. 2018 Aug 7;14:1379-1385. doi: 10.2147/TCRM.S174693. eCollection 2018. PubMed PMID: 30122937; PubMed Central PMCID: PMC6086094.

18: Liu SJ, Liu XY, Li JH, Guo J, Li F, Gui Y, Li XH, Yang L, Wu CY, Yuan Y, Li JJ. Gastrodin attenuates microglia activation through renin-angiotensin system and Sirtuin3 pathway. Neurochem Int. 2018 Nov;120:49-63. doi: 10.1016/j.neuint.2018.07.012. Epub 2018 Jul 31. PubMed PMID: 30075231.

19: Enya K, Saji BT, Kato T, Okamoto H, Koumura E. Pharmacokinetics of a Single Dose of Azilsartan in Pediatric Patients: A Phase 3, Open-Label, Multicenter Study. Adv Ther. 2018 Aug;35(8):1181-1190. doi: 10.1007/s12325-018-0754-5. Epub 2018 Jul 19. PubMed PMID: 30027478; PubMed Central PMCID: PMC6096965.

20: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK501769/ PubMed PMID: 30000828.