133040-01-4

Basic information

• Product Name: EPROSARTAN
• Synonyms: EPROSARTAN;Eprosartan Mysylate;(E)-3-[2-Butyl-1-[(4-carboxyphenyl)-methyl]imidazol-5-l]-2-(2-thienylmethyl)-2-propenoic Acid;((E)-3-[2-Butyl-1-[(4-carboxyphenyl)methyl]imidazol-5-yl]-2-(2-thienylmethyl)-2-propenoic Acid;SKF-108566);(E)- α-[[2-Butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-y1]methylene]2-thiophenepropanoic acid;SKF-108566J;Teveten
• CAS NO: 133040-01-4
• Molecular Formula: C₂₃H₂₄N₂O₄S
• Molecular Weight: 424.51
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Heterocycles;Impurities;Intermediates;Aromatics
• Mol File: 133040-01-4.mol

Chemical Properties

• Melting Point: 250-253°C
• Boiling Point: 660.6°C at 760 mmHg
• Flash Point: 353.3°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 2.37E-18mmHg at 25°C
• Refractive Index: 1.627
• Storage Temp.: -20°C Freezer
• Solubility: Dichloromethane (Slightly), Methanol (Slightly)
• CAS DataBase Reference: EPROSARTAN(CAS DataBase Reference)
• NIST Chemistry Reference: EPROSARTAN(133040-01-4)
• EPA Substance Registry System: EPROSARTAN(133040-01-4)

Safety Data

• Hazardous Substances Data: 133040-01-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Eprosartan is used as an antihypertensive agent for the treatment of hypertension. It functions as a prototype of the imidazoleacrylic acid angiotensin II receptor antagonists, helping to regulate blood pressure by blocking the effects of angiotensin II, a potent vasoconstrictor.
Used in Research and Development:
Eprosartan (E590100) is utilized as an impurity in the development and testing of new drugs related to hypertension treatment. This application aids in understanding the drug's behavior, side effects, and potential interactions with other substances.
Used in Chemical Synthesis:
Eprosartan serves as a starting point for the synthesis of various related compounds in the imidazoleacrylic acid angiotensin II receptor antagonist class. This application is crucial for the development of new drugs with improved properties or alternative mechanisms of action.

Originator

SmithKline Beecham (UK)

Clinical Use

Angiotensin-II antagonistHypertension

Drug interactions

Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect.Analgesics: antagonism of hypotensive effect and increased risk of renal impairment with NSAIDs; hyperkalaemia with ketorolac and other NSAIDs.Antihypertensives: increased risk of hyperkalaemia hypotension and renal impairment with ACE inhibitors and aliskiren.Ciclosporin: increased risk of hyperkalaemia and nephrotoxicity.Diuretics: enhanced hypotensive effect; hyperkalaemia with potassium-sparing diuretics.Epoetin: increased risk of hyperkalaemia; antagonism of hypotensive effect.Lithium: reduced excretion, possibility of enhanced lithium toxicity.Potassium salts: increased risk of hyperkalaemia.Tacrolimus: increased risk of hyperkalaemia and nephrotoxicity.

Metabolism

Following oral and intravenous dosing with [14C] eprosartan in human subjects, eprosartan was the only drug-related compound found in the plasma and faeces. In the urine, approximately 20% of the radioactivity excreted was an acyl glucuronide of eprosartan with the remaining 80% being unchanged eprosartanEprosartan is eliminated by both biliary and renal excretion. Following intravenous [14C] eprosartan, about 61% of radioactivity is recovered in the faeces and about 37% in the urine. Following an oral dose of [14C] eprosartan, about 90% of radioactivity is recovered in the faeces and about 7% in the urine.

InChI:InChI=1/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+

Upstream product

• 133040-06-9 methyl (E)-3-<2-butyl-1-<(4-carbomethoxyphenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenoate 
• 50790-93-7 2-butyl-1H-imidazole 
• 133040-03-6 2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde 
• 133040-04-7 2-butyl-1-(4-carbomethoxybenzyl)-5-<2-carbomethoxy-1-hydroxy-3-(2-thienyl)propyl>imidazole 
• 154371-62-7 1-(benzyloxymethyl)-2-butyl-4,5-diiodoimidazole 
• 154371-51-4 1-(benzyloxymethyl)-2-butyl-4-iodoimidazole-5-carboxaldehyde 
• 16862-05-8 methyl 3-(2-thienyl)propanoate 
• 83857-96-9 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde 
• 143468-96-6 3-ethoxy-3-oxo-2-(thien-3-ylmethyl)propanoic acid 
• 1104528-98-4 (E)-α-[[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-2-thiophene propanoic acid acetate 
• 133486-13-2 ethyl (αE)-α-[[2-n-butyl-1-[[4-(methoxycarbonyl)phenyl]methyl]-1H-imidazol-5-yl]methylene-2-thiophene]propionate 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 133040-02-5 2-butyl-4-chloro-1-<(4-carbomethoxyphenyl)methyl>-1H-imidazole-5-carboxaldehyde 
• 148674-60-6 2-(thienylmethyl)cyanoacetic acid 

Downstream Products

• 148674-39-9 SB 206328 
• 1104528-98-4 (E)-α-[[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-2-thiophene propanoic acid acetate 
• 133486-07-4 (E)-3-<2-butyl-1-<(4-carboxamidophenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenamide 
• 148674-52-6 4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzonitrile 

Related news

Enhanced dissolution/caco-2 permeability, pharmacokinetic and pharmacodynamic performance of re-dispersible EPROSARTAN (cas 133040-01-4) mesylate nanopowder09/10/2019

Eprosartan mesylate is an angiotensin receptor blocker which suffers from extremely poor bioavailability owing to its poor solubility and poor permeability. The rationale of the present work was to design the drug delivery system capable of overcoming these constraints. Nanoformulation of eprosa...detailed

Risk assessment and QbD based optimization of an EPROSARTAN (cas 133040-01-4) mesylate nanosuspension: In-vitro characterization, PAMPA and in-vivo assessment09/08/2019

Quality by design (QbD) principles were implemented to understand the product and process variables of sonoprecipitation technique, for preparation of eprosartan mesylate (EM) nanosuspension. Quality risk management approach was utilized to identify and assess high-risk attributes affecting crit...detailed

Original articleEffectiveness of EPROSARTAN (cas 133040-01-4) in diabetic hypertensive patients09/07/2019

BackgroundThe aim of this study was to compare the effectiveness and safety of eprosartan in reducing blood pressure in a group of diabetic patients and a group of non-diabetic patients in a primary care setting.detailed

Pulmonary, gastrointestinal and urogenital pharmacologyAmeliorative effect of EPROSARTAN (cas 133040-01-4) on high-fat diet/streptozotocin-induced early diabetic nephropathy in rats09/06/2019

Diabetic nephropathy becomes the single most frequent cause of end-stage renal disease. The present study aimed therefore to investigate possible protective effect of eprosartan, an angiotensin II type 1 receptor blocker, on high-fat diet/streptozotocin-induced early diabetic nephropathy in rats...detailed

Original articleFormulation and characterization of novel soft nanovesicles for enhanced transdermal delivery of EPROSARTAN (cas 133040-01-4) mesylate09/05/2019

The objective of the present work was to formulate, optimize and evaluate the potential of novel soft nanovesicles i.e. nano-transfersomes, containing eprosartan mesylate (EM) for transdermal delivery. Nano-transfersomes of EM were developed using Phospholipon 90G, Span 80 (SP) and sodium deoxyc...detailed

Spectroscopic and molecular docking studies of the binding of the angiotensin II receptor blockers (ARBs) azilsartan, EPROSARTAN (cas 133040-01-4) and olmesartan to bovine serum albumin09/04/2019

Angiotensin receptor blockers (ARBs) represent a group of widely used therapeutic agents for the effective control of hypertension and other cardiovascular problems. Herein, the interactions of three important members of the ARBs (azilsartan, eprosartan and olmesartan) with bovine serum albumin ...detailed

EPROSARTAN (cas 133040-01-4) mesylate loaded bilosomes as potential nano-carriers against diabetic nephropathy in streptozotocin-induced diabetic rats09/03/2019

The objective of the present study was to formulate eprosartan mesylate loaded nano-bilosomes and investigates its potential for controlling streptozotocin induced diabetes nephropathy in Wistar rats. The eprosartan mesylate loaded nano-bilosomes comprising of various ratios of soybean phosphati...detailed

Original research articleOATP and MRP2-mediated hepatic uptake and biliary excretion of EPROSARTAN (cas 133040-01-4) in rat and human09/02/2019

BackgroundEprosartan is an angiotensin II receptor antagonist, used in the treatment of hypertension and heart failure in clinical patients. The objective of this study was to clarify the mechanism underlying hepatic uptake and biliary excretion of eprosartan in rats and humans.detailed

Relevant articles and documents

Multicomponent Pharmaceutical Adducts of α-Eprosartan: Physicochemical Properties and Pharmacokinetic Study

Pharmaceutical adducts of α-eprosartan (EPR) with nicotinamide (NIC) and p-hydroxy benzoic acid (PHB) were prepared by a liquid assisted grinding technique. Prior to conducting this study, the single crystal structure of EPR was determined. This study was designed to improve the pH-dependent solubility and dissolution rate of EPR and hence its oral absorption across the gastrointestinal tract. Initially, differential scanning calorimetry and powder X-ray diffractometry were used as a screening tool for rapid cocrystal or eutectic mixture screening. The eutectic mixture of EPR with PHB in a 1:3 stoichiometry ratio shows a better solubility and dissolution rate in all aqueous buffers as compared to EPR/NIC cocrystals and pure EPR. The EPR/NIC cocrystal in a 1:1 stoichiometry ratio shows a better dissolution rate initially as compared to pure EPR but does revert back to EPR within the first 30 min in pH 1.2 and 6.8. Absorption and desorption profile of EPR adducts are reversible, suggesting no solid state transformation under experimental conditions. A significant increase in oral bioavailability in overnight fasted Sprague-Dawley rats is achieved with the EPR/NIC cocrystal (2.4-fold) and EPR/PHB eutectics (6.1-fold), even when the cocrystal transformation is suspected based on in vitro studies.

COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE

To characterize the urinary exosome miRNome, microarrays were used to identify the miRNA spectrum present within urinary exosomes from ten individuals that were previously classified for their salt sensitivity status. The present application discloses distinct patterns of selected exosomal miRNA expression that were different between salt-sensitive (SS), salt-resistant (SR), and inverse salt-sensitive (ISS) individuals. These miRNAs can be useful as biomarkers either individually or as panels comprising multiple miRNAs. The present invention provides compositions and methods for identifying, diagnosing, monitoring, and treating subjects with salt sensitivity of blood pressure. The applications discloses panels of miRNAs useful for comparing profiles, and in some cases one or more of the miRNAs in a panel can be used. The miRNAs useful for distinguishing SS and SR or ISS and SR subjects. One or more of the 45 miRNAs can be used. Some of the miRNAs have not been previously reported to be circulating. See those miRNAs with asterisks in FIG. 1 and below. The present invention encompasses the use of one or more of these markers for identifying and diagnosing SR, SS, and ISS subjects.

PROCESS FOR EPROSARTAN INTERMEDIATE

The present invention provides an improved process for preparation of (E)-α-[[2-butyl-1-[[4-(methoxycarbonyl)phenyl]methyl]-1H-imidazole-5-yl]methylene]-2-thiophene propanoic acid ethyl ester in high purity and in high yield. Thus, for example, 4-[[2-buty

PHARMACEUTICAL FORMULATION CONTAINING ANGIOTENSIN-II RECEPTOR BLOCKER

The present invention provides a pharmaceutical formulation containing an angiotensin-II receptor blocker and a release-control material as a pharmacologically active ingredient and a pharmaceutical formulation comprising an immediate-release compartment and an extended-release compartment. The immediate-release compartment contains an agent as a pharmacologically active ingredient for preventing and inhibiting hepatitis and the extended-release compartment has an angiotensin-II receptor blocker as a pharmacologically active ingredient. The formulation of the present invention maximizes the effectiveness on pharmacologically and clinically lowering blood pressure and preventing complications when taking the formulation, helps to avoid interaction with a drug which is metabolized by the same enzyme in the liver, and prevents and inhibits the incidence of drug-induced hepatitis which is caused by drug administration for a long time.

AN IMPROVED PROCESS FOR THE PREPARATION OF PURE EPROSARTANAND ITS PHARMACEUTICAL ACCEPTABLE SALTS

The present invention relates to an improved process for preparation of pure Eprosartan and its pharmaceutical acceptable salts comprising the steps of: a) treating the Eprosartan with hydrochloric acid; b) suspending the resulted Eprosartan hydrochloride

AN IMPROVED PROCESS FOR THE PREPARATION OF EPROSARTAN

The present invention provides an improved process for the preparation of Eprosartan or its pharmaceutically acceptable salt comprising the steps of: condensing compound of formula (a) with compound of formula (b) in presence of a catalyst, in a solvent to get a compound of formula (c), and hydrolyzing the compound of formula (c) to get Eprosartan and optionally converting Eprosartan to its pharmaceutically acceptable salt. The present invention also relates to process for the preparation of compound of formula (c) by condensing compound of formula (a) with compound of formula (b) in presence of dehydrating agent.

Synthesis and biological evaluation of [carboxyl-11C]eprosartan

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IMPROVED PROCESS FOR EPROSARTAN INTERMEDIATE

The present invention provides an improved process for preparation of (E)-α-[[2-butyl-1-[[4-(methoxycarbonyl)phenyl]methyl]-1 H-imidazole-5-yl] methylene]-2-thiophene propanoic acid ethyl ester in high purity and in high yield. Thus, for example, 4-[[2-bu

IMPROVED PROCESS FOR MANUFACTURING ANHYDROUS (E)-3-[2-BUTYL-1- {(4-CARBOXYPHENYL) METHYL}-1H-IMIDAZOLE-5-YL]-(THIOPHEN-2- YLMETHYL)PROP-2-ENOIC ACID METHANE SULFONATE

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EPROSARTAN MESYLATE CRYSTALLINE PARTICLES AND A PROCESS FOR PREPARING PURE EPROSARTAN

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