Synonym
Eprosartan; Teveten; Navixen; SK&F108566; SK&F-108566; SK&F 108566; SKF 108566; SKF108566; SKF-108566; SKB 108566; SKB108566; SKB-108566;
IUPAC/Chemical Name
4-[[2-Butyl-5-[(E)-2-carboxy-3-thiophen-2-ylprop-1-enyl]imidazol-1-yl]methyl]benzoic acid
InChi Key
OROAFUQRIXKEMV-LDADJPATSA-N
InChi Code
InChI=1S/C23H24N2O4S/c1-2-3-6-21-24-14-19(12-18(23(28)29)13-20-5-4-11-30-20)25(21)15-16-7-9-17(10-8-16)22(26)27/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29)/b18-12+
SMILES Code
O=C(O)C1=CC=C(CN2C(/C=C(C(O)=O)\CC3=CC=CS3)=CN=C2CCCC)C=C1
Purity
>96% (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
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:
Eprosartan (SKF-108566J free base) is an angiotensin II receptor antagonist, used as an antihypertensive. Eprosartan binds angiotensin II receptor with IC50s of 9.2 nM and 3.9 nM in rat and human adrenal cortical membranes, respectively.
In vitro activity:
Although candesartan and telmisartan exhibited weaker inverse agonist activity for N111G- compared with WT-AT1 receptors, only eprosartan exhibited robust inverse agonist activity for both N111G- and WT- AT1 receptors.
Reference: Br J Pharmacol. 2018 Jun; 175(12): 2454–2469. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5980637/
In vivo activity:
Pretreatment with EPRO (eprosartan) opposed motor impairment and decreased oxidative and apoptotic mediators in the hippocampus of rats. The anti-inflammatory activity of EPRO was revealed by downregulation of nuclear factor-kappa B and tumor necrosis factor-β levels and (C-X-C motif) ligand 1 messenger RNA (mRNA) expression. Moreover, the study confirmed the role of EPRO against a unique pathway of hypoxia-inducible factor-1α and its subsequent inflammatory mediators. Furthermore, upregulation of caveolin-1 mRNA level was also observed along with decreased oxidative stress marker levels and brain edema. Therefore, EPRO showed neuroprotective effects in MCAO-induced cerebral ischemia in rats via attenuation of oxidative, apoptotic, and inflammatory pathways.
Reference: J Biochem Mol Toxicol. 2021 May 3:e22796. https://pubmed.ncbi.nlm.nih.gov/33942446/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
125.0 |
294.46 |
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
424.51
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. Takezako T, Unal H, Karnik SS, Node K. The non-biphenyl-tetrazole angiotensin AT1 receptor antagonist eprosartan is a unique and robust inverse agonist of the active state of the AT1 receptor. Br J Pharmacol. 2018 Jun;175(12):2454-2469. doi: 10.1111/bph.14213. Epub 2018 May 6. PMID: 29570771; PMCID: PMC5980637.
2. Saad MAE, Fahmy MIM, Sayed RH, El-Yamany MF, El-Naggar R, Hegazy AAE, Al-Shorbagy M. Eprosartan: A closer insight into its neuroprotective activity in rats with focal cerebral ischemia-reperfusion injury. J Biochem Mol Toxicol. 2021 May 3:e22796. doi: 10.1002/jbt.22796. Epub ahead of print. PMID: 33942446.
3. Morsy MA, Heeba GH, Mahmoud ME. Ameliorative effect of eprosartan on high-fat diet/streptozotocin-induced early diabetic nephropathy in rats. Eur J Pharmacol. 2015 Mar 5;750:90-7. doi: 10.1016/j.ejphar.2015.01.027. Epub 2015 Jan 24. Erratum in: Eur J Pharmacol. 2015 Sep 5;762:487. PMID: 25625658.
In vitro protocol:
1. Takezako T, Unal H, Karnik SS, Node K. The non-biphenyl-tetrazole angiotensin AT1 receptor antagonist eprosartan is a unique and robust inverse agonist of the active state of the AT1 receptor. Br J Pharmacol. 2018 Jun;175(12):2454-2469. doi: 10.1111/bph.14213. Epub 2018 May 6. PMID: 29570771; PMCID: PMC5980637.
In vivo protocol:
1. Saad MAE, Fahmy MIM, Sayed RH, El-Yamany MF, El-Naggar R, Hegazy AAE, Al-Shorbagy M. Eprosartan: A closer insight into its neuroprotective activity in rats with focal cerebral ischemia-reperfusion injury. J Biochem Mol Toxicol. 2021 May 3:e22796. doi: 10.1002/jbt.22796. Epub ahead of print. PMID: 33942446.
2. Morsy MA, Heeba GH, Mahmoud ME. Ameliorative effect of eprosartan on high-fat diet/streptozotocin-induced early diabetic nephropathy in rats. Eur J Pharmacol. 2015 Mar 5;750:90-7. doi: 10.1016/j.ejphar.2015.01.027. Epub 2015 Jan 24. Erratum in: Eur J Pharmacol. 2015 Sep 5;762:487. PMID: 25625658.
1: Takezako T, Unal H, Karnik SS, Node K. Current topics in angiotensin II type 1 receptor research: Focus on inverse agonism, receptor dimerization and biased agonism. Pharmacol Res. 2017 Sep;123:40-50. doi: 10.1016/j.phrs.2017.06.013. Epub 2017 Jun 23. Review. PubMed PMID: 28648738; PubMed Central PMCID: PMC5567726.
2: Yang R, Luo Z, Liu Y, Sun M, Zheng L, Chen Y, Li Y, Wang H, Chen L, Wu M, Zhao H. Drug Interactions with Angiotensin Receptor Blockers: Role of Human Cytochromes P450. Curr Drug Metab. 2016;17(7):681-91. Review. PubMed PMID: 27216792.
3: Castilla-Guerra L, Fernandez-Moreno Mdel C. Chronic Management of Hypertension after Stroke: The Role of Ambulatory Blood Pressure Monitoring. J Stroke. 2016 Jan;18(1):31-7. doi: 10.5853/jos.2015.01102. Epub 2015 Dec 17. Review. PubMed PMID: 26687120; PubMed Central PMCID: PMC4747066.
4: Zaiken K, Hudd TR, Cheng JW. A review of the use of angiotensin receptor blockers for the prevention of cardiovascular events in patients with essential hypertension without compelling indications. Ann Pharmacother. 2013 May;47(5):686-93. doi: 10.1345/aph.1R273. Epub 2013 Apr 12. Review. PubMed PMID: 23585649.
5: Spinar J, Vitovec J. [AII antagonists in the treatment of hypertension and prevention of CVA]. Vnitr Lek. 2013 Jan;59(1):71-8. Review. Czech. PubMed PMID: 23565527.
6: Michel MC, Foster C, Brunner HR, Liu L. A systematic comparison of the properties of clinically used angiotensin II type 1 receptor antagonists. Pharmacol Rev. 2013 Mar 13;65(2):809-48. doi: 10.1124/pr.112.007278. Print 2013 Apr. Review. PubMed PMID: 23487168.
7: Imaizumi S, Miura S, Yahiro E, Uehara Y, Komuro I, Saku K. Class- and molecule-specific differential effects of angiotensin II type 1 receptor blockers. Curr Pharm Des. 2013;19(17):3002-8. Review. PubMed PMID: 23176212.
8: Spinar J, Vítovec J. [AII antagonists (candesartan and irbesartan) in the treatment of cardiovascular diseases]. Vnitr Lek. 2012 Oct;58(10):755-60. Review. Czech. PubMed PMID: 23121062.
9: Awada A. [Primary and secondary prevention of ischemic stroke]. J Med Liban. 2011 Oct-Dec;59(4):213-9. Review. French. PubMed PMID: 22746010.
10: Kurtz TW, Kajiya T. Differential pharmacology and benefit/risk of azilsartan compared to other sartans. Vasc Health Risk Manag. 2012;8:133-43. doi: 10.2147/VHRM.S22595. Epub 2012 Feb 28. Review. PubMed PMID: 22399858; PubMed Central PMCID: PMC3295635.
11: Derosa G, Maffioli P. Nifedipine and telmisartan for the treatment of hypertension: the TALENT study. Expert Rev Cardiovasc Ther. 2011 Dec;9(12):1499-503. doi: 10.1586/erc.11.155. Review. PubMed PMID: 22103868.
12: Verdecchia P, Angeli F, Repaci S, Mazzotta G, Gentile G, Reboldi G. Comparative assessment of angiotensin receptor blockers in different clinical settings. Vasc Health Risk Manag. 2009;5:939-48. Epub 2009 Nov 16. Review. PubMed PMID: 19997575; PubMed Central PMCID: PMC2788599.
13: Plosker GL. Eprosartan: a review of its use in hypertension. Drugs. 2009;69(17):2477-99. doi: 10.2165/11203980-000000000-00000. Review. PubMed PMID: 19911859.
14: Armario P, de la Sierra A. Antihypertensive treatment and stroke prevention: are angiotensin receptor blockers superior to other antihypertensive agents? Ther Adv Cardiovasc Dis. 2009 Jun;3(3):197-204. doi: 10.1177/1753944709104164. Epub 2009 May 14. Review. PubMed PMID: 19443514.
15: Theodoratou D, Maniadakis N, Fragoulakis V, Stamouli E. Analysis of published economic evaluations of angiotensin receptor blockers. Hellenic J Cardiol. 2009 Mar-Apr;50(2):105-18. Review. PubMed PMID: 19329412.
16: Al Khalaf MM, Thalib L, Doi SA. Cardiovascular outcomes in high-risk patients without heart failure treated with ARBs: a systematic review and meta-analysis. Am J Cardiovasc Drugs. 2009;9(1):29-43. doi: 10.2165/00129784-200909010-00004. Review. PubMed PMID: 19178130.
17: Blankestijn PJ, Rupp H. Clinical profile of eprosartan: a different angiotensin II receptor blocker. Cardiovasc Hematol Agents Med Chem. 2008 Oct;6(4):253-7. Review. PubMed PMID: 18855637; PubMed Central PMCID: PMC2748700.
18: Rupp H. Risk reduction by preventing stroke: need for blockade of angiotensin II and catecholamines? Curr Med Res Opin. 2007 Nov;23 Suppl 5:S25-9. doi: 10.1185/030079907X260737. Review. PubMed PMID: 18093411.
19: Shlyakhto E. Observational Study on Cognitive function And systolic blood pressure Reduction (OSCAR): preliminary analysis of 6-month data from > 10,000 patients and review of the literature. Curr Med Res Opin. 2007 Nov;23 Suppl 5:S13-8. doi: 10.1185/030079907X260719. Review. PubMed PMID: 18093409.
20: Ram CV. Angiotensin blockade with eprosartan: vascular and functional implications. Curr Med Res Opin. 2007 Nov;23 Suppl 5:S5-11. doi: 10.1185/030079907X260700. Review. PubMed PMID: 18093408.
