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
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
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/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
89.0 |
159.33 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
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.
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.
