Eprosartan Mesylate | CAS#144143-96-4 | Angiotensin II Receptor Antagonist

MedKoo Cat#: 317780 | Name: Eprosartan Mesylate

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Description:

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

Eprosartan is an angiotensin II receptor antagonist used for the treatment of high blood pressure. It is marketed in the United States as Teveten by Abbvier. Eprosartan is sometimes paired with hydrochlorothiazide, whereupon it is marketed in the US as Teveten HCT and elsewhere as Teveten Plus.The drug acts on the renin-angiotensin system to decrease total peripheral resistance in two ways. First, it blocks the binding of angiotensin II to AT1 receptors in vascular smooth muscle, causing vascular dilatation. Second, it inhibits sympathetic norepinephrine production, further reducing blood pressure. As with other angiotensin II receptor antagonists, eprosartan is generally better tolerated than enalapril (an ACE inhibitor), especially among the elderly.

Chemical Structure

Eprosartan Mesylate

CAS#144143-96-4 (mesylate)

Theoretical Analysis

MedKoo Cat#: 317780

Name: Eprosartan Mesylate

CAS#: 144143-96-4 (mesylate)

Chemical Formula: C24H28N2O7S2

Exact Mass: 0.0000

Molecular Weight: 520.62

Elemental Analysis: C, 55.37; H, 5.42; N, 5.38; O, 21.51; S, 12.32

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 Weeks
5g	USD 650.00	2 Weeks

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Related CAS #

133040-01-4 (free) 144143-96-4 (mesylate)

Synonym

Eprosartan mesylate; Eprosartan mesilate; Eprosartan methanesulfonate; Eprosartan monomethanesulfonate; Teveten; Futuran; Navixen; Regulaten; SK&F108566; SK&F-108566; SK&F 108566; SKF 108566J; SKF108566J; SKF-108566J;

IUPAC/Chemical Name

4-[[2-butyl-5-[(E)-2-carboxy-3-thiophen-2-ylprop-1-enyl]imidazol-1-yl]methyl]benzoic acid;methanesulfonic acid

InChi Key

DJSLTDBPKHORNY-XMMWENQYSA-N

InChi Code

InChI=1S/C23H24N2O4S.CH4O3S/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;1-5(2,3)4/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29);1H3,(H,2,3,4)/b18-12+;

SMILES Code

CCCCC1=NC=C(N1CC2=CC=C(C=C2)C(=O)O)/C=C(\CC3=CC=CS3)/C(=O)O.CS(=O)(=O)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:

Eprosartan mesylate (SKF-108566J) is an angiotensin II receptor antagonist, used as an antihypertensive.

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	59.3	113.96
	DMSO:PBS (pH 7.2) (1:1)	0.5	0.96
	DMF	30.0	57.62
	Ethanol	8.0	15.37

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 520.62 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:

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: Ahad A, Raish M, Ahmad A, Al-Jenoobi FI, Al-Mohizea AM. Eprosartan mesylate loaded bilosomes as potential nano-carriers against diabetic nephropathy in streptozotocin-induced diabetic rats. Eur J Pharm Sci. 2018 Jan 1;111:409-417. doi: 10.1016/j.ejps.2017.10.012. Epub 2017 Oct 10. PMID: 29030177. 2: Ahad A, Bin Jardan YA, Hassan MZ, Raish M, Ahmad A, Al-Mohizea AM, Al-Jenoobi FI. Formulation and characterization of eprosartan mesylate and β-cyclodextrin inclusion complex prepared by microwave technology. Drug Deliv. 2022 Dec;29(1):1512-1522. doi: 10.1080/10717544.2022.2072540. PMID: 35549506; PMCID: PMC9116268. 3: Patil MS, Shirkhedkar AA. Self-microemulsifying Drug Delivery System for Solubility and Bioavailability Enhancement of Eprosartan Mesylate: Preparation, In-vitro, and In-vivo Evaluation. Pharm Nanotechnol. 2023;11(1):56-69. doi: 10.2174/2211738510666220915100150. PMID: 36111774. 4: Yousaf AM, Zulfiqar S, Shahzad Y, Hussain T, Mahmood T, Jamshaid M. The preparation and physicochemical characterization of eprosartan mesylate-laden polymeric ternary solid dispersions for enhanced solubility and dissolution rate of the drug. Polim Med. 2018 Jul-Dec;48(2):69-75. doi: 10.17219/pim/102976. PMID: 30916494. 5: Conter HS, McKay DW, Reiz RJ. Eprosartan mesylate effectively reduces systolic and diastolic blood pressure in a Canadian primary care setting. Can J Cardiol. 2004 Oct;20 Suppl C:6C-10C. PMID: 16807617. 6: Sheng J, Venkatesh GM, Duddu SP, Grant DJ. Dehydration behavior of eprosartan mesylate dihydrate. J Pharm Sci. 1999 Oct;88(10):1021-9. doi: 10.1021/js9900250. PMID: 10514350. 7: Anandakumar K, Santhi DV, Jothieswari D, Subathrai R, Vetrichelvan T. Development and Validation of a UV Spectrophotometric Method for the Simultaneous Estimation of Eprosartan Mesylate and Hydrochlorothiazide in Bulk and Formulations. Indian J Pharm Sci. 2011 Sep;73(5):569-72. doi: 10.4103/0250-474X.99017. PMID: 22923871; PMCID: PMC3425070. 8: Ramkanth S, Anitha P, Gayathri R, Mohan S, Babu D. Formulation and design optimization of nano-transferosomes using pioglitazone and eprosartan mesylate for concomitant therapy against diabetes and hypertension. Eur J Pharm Sci. 2021 Jul 1;162:105811. doi: 10.1016/j.ejps.2021.105811. Epub 2021 Mar 20. PMID: 33757828. 9: Shekhawat P, Bagul M, Edwankar D, Pokharkar V. Enhanced dissolution/caco-2 permeability, pharmacokinetic and pharmacodynamic performance of re-dispersible eprosartan mesylate nanopowder. Eur J Pharm Sci. 2019 Apr 30;132:72-85. doi: 10.1016/j.ejps.2019.02.021. Epub 2019 Feb 22. PMID: 30797937. 10: Ahad A, Al-Saleh AA, Al-Mohizea AM, Al-Jenoobi FI, Raish M, Yassin AEB, Alam MA. Pharmacodynamic study of eprosartan mesylate-loaded transfersomes Carbopol® gel under Dermaroller® on rats with methyl prednisolone acetate-induced hypertension. Biomed Pharmacother. 2017 May;89:177-184. doi: 10.1016/j.biopha.2017.01.164. Epub 2017 Feb 24. PMID: 28237913. 11: Qian JJ, Hu XR, Gu J, Wu SX. Eprosartan mesylate, an angiotensin II receptor antagonist. Acta Crystallogr Sect E Struct Rep Online. 2011 Apr 1;67(Pt 4):o770-1. doi: 10.1107/S1600536811006659. Epub 2011 Mar 2. PMID: 21754064; PMCID: PMC3099799. 12: Hacioğlu F, Onal A. Determination of eprosartan mesylate and hydrochlorothiazide in tablets by derivative spectrophotometric and high- performance liquid chromatographic methods. J Chromatogr Sci. 2012 Sep;50(8):688-93. doi: 10.1093/chromsci/bms037. Epub 2012 May 10. PMID: 22576732. 13: Punzi HA, Punzi CF. Once-daily eprosartan mesylate in the treatment of elderly patients with isolated systolic hypertension: data from a 13-week double-blind, placebo-controlled, parallel, multicenter study. J Hum Hypertens. 2004 Sep;18(9):655-61. doi: 10.1038/sj.jhh.1001704. PMID: 15042114. 14: Ahad A, Al-Saleh AA, Al-Mohizea AM, Al-Jenoobi FI, Raish M, Yassin AEB, Alam MA. Formulation and characterization of novel soft nanovesicles for enhanced transdermal delivery of eprosartan mesylate. Saudi Pharm J. 2017 Nov;25(7):1040-1046. doi: 10.1016/j.jsps.2017.01.006. Epub 2017 Feb 2. PMID: 29158713; PMCID: PMC5681305. 15: Ahad A, Al-Saleh AA, Al-Mohizea AM, Al-Jenoobi FI, Raish M, Yassin AEB, Alam MA. Formulation and characterization of Phospholipon 90 G and tween 80 based transfersomes for transdermal delivery of eprosartan mesylate. Pharm Dev Technol. 2018 Oct;23(8):787-793. doi: 10.1080/10837450.2017.1330345. Epub 2017 May 26. PMID: 28504046. 16: Dangre P, Gilhotra R, Dhole S. Formulation and statistical optimization of self-microemulsifying drug delivery system of eprosartan mesylate for improvement of oral bioavailability. Drug Deliv Transl Res. 2016 Oct;6(5):610-21. doi: 10.1007/s13346-016-0318-7. PMID: 27465619. 17: Shekhawat P, Pokharkar V. Risk assessment and QbD based optimization of an Eprosartan mesylate nanosuspension: In-vitro characterization, PAMPA and in-vivo assessment. Int J Pharm. 2019 Aug 15;567:118415. doi: 10.1016/j.ijpharm.2019.06.006. Epub 2019 Jun 5. PMID: 31175989. 18: Teitelbaum I, Chilvers M, Reiz RJ. The angiotensin receptor blocker eprosartan mesylate reduces pulse pressure in isolated systolic hypertension. Can J Cardiol. 2004 Oct;20 Suppl C:11C-16C. PMID: 16807618. 19: Kalariya PD, Kumar Talluri MV, Gaitonde VD, Devrukhakar PS, Srinivas R. Quality by design: a systematic and rapid liquid chromatography and mass spectrometry method for eprosartan mesylate and its related impurities using a superficially porous particle column. J Sep Sci. 2014 Aug;37(16):2160-71. doi: 10.1002/jssc.201301364. Epub 2014 Jul 10. PMID: 24913516. 20: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2002 May;24(4):217-48. PMID: 12092009.

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