Olmesartan medoxomil | CAS#144689-63-4

Olmesartan medoxomil
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318384

CAS#: 144689-63-4 (medoxomil)

Description: Olmesartan medoxomil is an angiotensin II receptor antagonist which has been used for the treatment of high blood pressure. An ester prodrug, it is completely and rapidly hydrolyzed to the active acid form, olmesartan.

Chemical Structure

Olmesartan medoxomil

CAS# 144689-63-4 (medoxomil)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318384
Name: Olmesartan medoxomil
CAS#: 144689-63-4 (medoxomil)
Chemical Formula: C29H30N6O6
Exact Mass: 558.22
Molecular Weight: 558.595
Elemental Analysis: C, 62.36; H, 5.41; N, 15.05; O, 17.18

Price and Availability

Size	Price	Availability	Quantity
1g	USD 275
2g	USD 550
5g	USD 850
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Olmesartan medoxomil; CS 866; CS-866; Olmetec; Olsertain; Azor; Benicar;

IUPAC/Chemical Name: 1H-Imidazole-5-carboxylic acid, 4-(1-hydroxy-1-methylethyl)-2-propyl-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester

InChi Key: UQGKUQLKSCSZGY-UHFFFAOYSA-N

InChi Code: InChI=1S/C29H30N6O6/c1-5-8-23-30-25(29(3,4)38)24(27(36)39-16-22-17(2)40-28(37)41-22)35(23)15-18-11-13-19(14-12-18)20-9-6-7-10-21(20)26-31-33-34-32-26/h6-7,9-14,38H,5,8,15-16H2,1-4H3,(H,31,32,33,34)

SMILES Code: O=C(C1=C(C(C)(O)C)N=C(CCC)N1CC2=CC=C(C3=CC=CC=C3C4=NN=NN4)C=C2)OCC5=C(C)OC(O5)=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

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Olmesartan medoxomil is a potent and selective angiotensin AT1 receptor inhibitor with IC50 of 66.2 μM.
In vitro activity:	To determine the roles of olmesartan in endothelial cell injuries during ox-LDL exposure, cellular vitality, nitrogen monoxide (NO) and Lactate Dehydrogenase (LDH) synthesis were. The results showed ox-LDL significantly increased the LDH synthesis and decreased cell vitality and NO synthesis in neonatal rat endothelial cells (Table 1). The addition of olmesartan to ox-LDL-stimulated endothelial cells significantly alleviated all the above harmful effects, including decreased cell vitality, increased LDH secretion, upregulated p-38 MAPK and overexpression of apoptotic genes such as Caspase-3 and Bax (Figure 1). These results indicated anti-apoptotic effects of olmesartan on endothelial cell injuries induced by ox-LDL in vitro. Reference: Int J Mol Sci. 2012;13(2):1512-23. https://pubmed.ncbi.nlm.nih.gov/22408405/
In vivo activity:	To determine the roles of olmesartan against ox-LDL insults in endothelial cells in vivo, mice were treated with ox-LDL (8.4 mg/kg/day), olmesartan (3 mg/kg/day) or both of them. Of course, the dose of ox-LDL at 8.4 mg/kg/day was insufficient to elevate the BP of mice. Three weeks later, it was found that BP was not significantly different among all groups of mice (Figure 2A). Interestingly, olmesartan significantly blunted the cellular injuries in terms of cell viability during the exposure of ox-LDL in vivo (Figure 2B–E). Moreover, treatment with olmesartan significantly decreased the gene expressions of Bax and Caspase-3 while increasing Bcl-2 levels in ox-LDL-treated mice. These results suggested olmesartan could protect endothelial cells against the injuries induced by ox-LDL in vivo. Reference: Int J Mol Sci. 2012;13(2):1512-23. https://pubmed.ncbi.nlm.nih.gov/22408405/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	89.0	159.33

Preparing Stock Solutions

The following data is based on the product molecular weight 558.60 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.

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

Formulation protocol:	1. Zhang H, Ma G, Yao Y, Qian H, Li W, Chen X, Jiang W, Zheng R. Olmesartan attenuates the impairment of endothelial cells induced by oxidized low density lipoprotein through downregulating expression of LOX-1. Int J Mol Sci. 2012;13(2):1512-23. doi: 10.3390/ijms13021512. Epub 2012 Feb 1. PMID: 22408405; PMCID: PMC3291974. 2. Zhang Y, Liang Q, Zhang Y, Hong L, Lei D, Zhang L. Olmesartan alleviates bleomycin-mediated vascular smooth muscle cell senescence via the miR-665/SDC1 axis. Am J Transl Res. 2020 Sep 15;12(9):5205-5220. PMID: 33042414; PMCID: PMC7540088. 3. Zhang H, Ma G, Yao Y, Qian H, Li W, Chen X, Jiang W, Zheng R. Olmesartan attenuates the impairment of endothelial cells induced by oxidized low density lipoprotein through downregulating expression of LOX-1. Int J Mol Sci. 2012;13(2):1512-23. doi: 10.3390/ijms13021512. Epub 2012 Feb 1. PMID: 22408405; PMCID: PMC3291974. 4. Suh SH, Choi HS, Kim CS, Kim IJ, Ma SK, Scholey JW, Kim SW, Bae EH. Olmesartan Attenuates Kidney Fibrosis in a Murine Model of Alport Syndrome by Suppressing Tubular Expression of TGFβ. Int J Mol Sci. 2019 Aug 6;20(15):3843. doi: 10.3390/ijms20153843. PMID: 31390839; PMCID: PMC6695622.
In vitro protocol:	1. Zhang H, Ma G, Yao Y, Qian H, Li W, Chen X, Jiang W, Zheng R. Olmesartan attenuates the impairment of endothelial cells induced by oxidized low density lipoprotein through downregulating expression of LOX-1. Int J Mol Sci. 2012;13(2):1512-23. doi: 10.3390/ijms13021512. Epub 2012 Feb 1. PMID: 22408405; PMCID: PMC3291974. 2. Zhang Y, Liang Q, Zhang Y, Hong L, Lei D, Zhang L. Olmesartan alleviates bleomycin-mediated vascular smooth muscle cell senescence via the miR-665/SDC1 axis. Am J Transl Res. 2020 Sep 15;12(9):5205-5220. PMID: 33042414; PMCID: PMC7540088.
In vivo protocol:	1. Zhang H, Ma G, Yao Y, Qian H, Li W, Chen X, Jiang W, Zheng R. Olmesartan attenuates the impairment of endothelial cells induced by oxidized low density lipoprotein through downregulating expression of LOX-1. Int J Mol Sci. 2012;13(2):1512-23. doi: 10.3390/ijms13021512. Epub 2012 Feb 1. PMID: 22408405; PMCID: PMC3291974. 2. Suh SH, Choi HS, Kim CS, Kim IJ, Ma SK, Scholey JW, Kim SW, Bae EH. Olmesartan Attenuates Kidney Fibrosis in a Murine Model of Alport Syndrome by Suppressing Tubular Expression of TGFβ. Int J Mol Sci. 2019 Aug 6;20(15):3843. doi: 10.3390/ijms20153843. PMID: 31390839; PMCID: PMC6695622.

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1: Choi EY, McKenna BJ. Olmesartan-Associated Enteropathy: A Review of Clinical and Histologic Findings. Arch Pathol Lab Med. 2015 Oct;139(10):1242-7. doi: 10.5858/arpa.2015-0204-RA. Review. PubMed PMID: 26414468.

2: Evdokimova AG, Ryzhova YV. [Up-to-Date Aspects of Antihypertensive Therapy from the Viewpoint of Cardio- and Nephroprotective Action: Olmesartan]. Antibiot Khimioter. 2015;60(5-6):34-40. Review. Russian. PubMed PMID: 26852494.

3: Ianiro G, Bibbò S, Montalto M, Ricci R, Gasbarrini A, Cammarota G. Systematic review: Sprue-like enteropathy associated with olmesartan. Aliment Pharmacol Ther. 2014 Jul;40(1):16-23. doi: 10.1111/apt.12780. Epub 2014 May 7. Review. PubMed PMID: 24805127.

4: Omboni S, Malacco E, Mallion JM, Fabrizzi P, Volpe M. Olmesartan vs. ramipril in elderly hypertensive patients: review of data from two published randomized, double-blind studies. High Blood Press Cardiovasc Prev. 2014 Mar;21(1):1-19. doi: 10.1007/s40292-013-0037-9. Epub 2014 Jan 17. Review. PubMed PMID: 24435506.

5: Miura S, Saku K. Recent progress in the treatment of cardiovascular disease using olmesartan. Clin Exp Hypertens. 2014;36(7):441-6. doi: 10.3109/10641963.2013.846363. Epub 2013 Oct 28. Review. PubMed PMID: 24164503.

6: Volpe M, Tocci G. Olmesartan in the treatment of hypertension in elderly patients: a review of the primary evidence. Drugs Aging. 2013 Dec;30(12):987-98. doi: 10.1007/s40266-013-0130-8. Review. PubMed PMID: 24170236.

7: Chrysant SG. Effectiveness of the fixed-dose combination of olmesartan/amlodipine/hydrochlorothiazide for the treatment of hypertension in patients stratified by age, race and diabetes, CKD and chronic CVD. Expert Rev Cardiovasc Ther. 2013 Sep;11(9):1115-24. doi: 10.1586/14779072.2013.827449. Review. PubMed PMID: 24073676.

8: Chrysant SG, Germino FW, Neutel JM. Olmesartan medoxomil-based antihypertensive therapy evaluated by ambulatory blood pressure monitoring: efficacy in high-risk patient subgroups. Am J Cardiovasc Drugs. 2012 Dec 1;12(6):375-89. doi: 10.2165/11636080-000000000-00000. Review. PubMed PMID: 23116225.

9: Tocci G, Paneni F, Passerini J, Volpe M. Triple combination therapy to improve blood pressure control: experience with olmesartan-amlodipine-hydrochlorothiazide therapy. Expert Opin Pharmacother. 2012 Dec;13(18):2687-97. doi: 10.1517/14656566.2012.745510. Epub 2012 Nov 21. Review. PubMed PMID: 23170911.

10: Wang L, Zhao JW, Liu B, Shi D, Zou Z, Shi XY. Antihypertensive effects of olmesartan compared with other angiotensin receptor blockers: a meta-analysis. Am J Cardiovasc Drugs. 2012 Oct 1;12(5):335-44. doi: 10.2165/11597390-000000000-00000. Review. PubMed PMID: 22920046.

11: Chatzikyrkou C, Menne J. Update on the ROADMAP clinical trial report: olmesartan for the prevention or delay of microalbuminuria development in type 2 diabetes. Expert Rev Cardiovasc Ther. 2012 Sep;10(9):1087-92. doi: 10.1586/erc.12.100. Review. PubMed PMID: 23098143.

12: Erdine S. Olmesartan/amlodipine: blood pressure lowering and beyond in special populations. Ther Adv Cardiovasc Dis. 2012 Feb;6(1):31-44. doi: 10.1177/1753944711432902. Epub 2012 Jan 5. Review. PubMed PMID: 22222315.

13: Khan BV. The effect of amlodipine besylate, losartan potassium, olmesartan medoxomil, and other antihypertensives on central aortic blood pressure and biomarkers of vascular function. Ther Adv Cardiovasc Dis. 2011 Oct;5(5):241-73. doi: 10.1177/1753944711420464. Epub 2011 Sep 5. Review. PubMed PMID: 21893558.

14: Fukui T, Munemura C, Maeta S, Ishida C, Murawaki Y. The Effects of Olmesartan and Alfacalcidol on Renoprotection and klotho Gene Expression in 5/6 Nephrectomized Spontaneously Hypertensive Rats. Yonago Acta Med. 2011 Sep;54(3):49-58. Epub 2011 Sep 1. Review. PubMed PMID: 24031129; PubMed Central PMCID: PMC3763788.

15: Tocci G, Volpe M. Fixed-combination therapy to improve blood pressure control: experience with olmesartan-based therapy. Expert Rev Cardiovasc Ther. 2011 Jul;9(7):829-40. doi: 10.1586/erc.11.59. Review. PubMed PMID: 21809963.

16: Chrysant SG. Triple-drug, fixed-dose combinations for the treatment of hypertension: focus on olmesartan/amlodipine/hydrochlorothiazide combination. Drugs Today (Barc). 2011 Mar;47(3):197-206. doi: 10.1358/dot.2011.47.3.1587028. Review. PubMed PMID: 21494697.

17: Mason RP. Optimal therapeutic strategy for treating patients with hypertension and atherosclerosis: focus on olmesartan medoxomil. Vasc Health Risk Manag. 2011;7:405-16. doi: 10.2147/VHRM.S20737. Epub 2011 Jun 24. Review. PubMed PMID: 21796255; PubMed Central PMCID: PMC3141913.

18: Tocci G, Volpe M. Olmesartan medoxomil for the treatment of hypertension in children and adolescents. Vasc Health Risk Manag. 2011;7:177-81. doi: 10.2147/VHRM.S11672. Epub 2011 Mar 31. Review. PubMed PMID: 21490943; PubMed Central PMCID: PMC3072741.

19: Deeks ED. Olmesartan medoxomil/amlodipine/hydrochlorothiazide: fixed-dose combination in hypertension. Drugs. 2011 Jan 22;71(2):209-20. doi: 10.2165/11206770-000000000-00000. Review. PubMed PMID: 21275446.

20: Ram CV. Olmesartan medoxomil, amlodipine besylate and hydrochlorothiazide triple combination for hypertension. Expert Rev Cardiovasc Ther. 2011 Jan;9(1):9-19. doi: 10.1586/erc.10.163. Review. PubMed PMID: 21166525.

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