Eprosartan

Base Information

• Chemical Name: Eprosartan
• CAS No.: 133040-01-4
• Molecular Formula: C23H24N2O4S
• Molecular Weight: 424.521
• UNII: 2KH13Z0S0Y
• ChEMBL ID: CHEMBL813
• DSSTox Substance ID: DTXSID0022989
• Metabolomics Workbench ID: 43151
• NCI Thesaurus Code: C61749
• Nikkaji Number: J380.264G,J553.931E
• Pharos Ligand ID: NBFH33SXA877
• Wikidata: Q784717
• Wikipedia: Eprosartan
• Mol file: 133040-01-4.mol

Synonyms:2-Thiophenepropanoic acid, alpha-((2-butyl-1-((4- carboxyphenyl)methyl)-lH-imidazol-5-yl)methylene)-, (E)-;eprosartan;SK and F 108566;SKF-108566;Teveten

Chemical Property of Eprosartan

Chemical Property:

• Vapor Pressure: 2.37E-18mmHg at 25°C
• Melting Point: 250-253 °C
• Refractive Index: 1.627
• Boiling Point: 660.6°C at 760 mmHg
• Flash Point: 353.3°C
• PSA: 120.66000
• Density: 1.26g/cm³
• LogP: 4.74440
• Storage Temp.: -20°C Freezer
• Solubility.: Dichloromethane (Slightly), Methanol (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 424.14567842
• Heavy Atom Count: 30
• Complexity: 618

Purity/Quality:

99% ^*data from raw suppliers

Eprosartan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Angiotensin II Receptor Antagonists
• Canonical SMILES: CCCCC1=NC=C(N1CC2=CC=C(C=C2)C(=O)O)C=C(CC3=CC=CS3)C(=O)O
• Isomeric SMILES: CCCCC1=NC=C(N1CC2=CC=C(C=C2)C(=O)O)/C=C(\CC3=CC=CS3)/C(=O)O
• Recent ClinicalTrials: Host Response Mediators in Coronavirus (COVID-19) Infection - Is There a Protective Effect of Losartan and Other ARBs on Outcomes of Coronavirus Infection?
• Recent EU Clinical Trials: A Prospective, Randomized, Double-Blind, Parallel-Group Study to Compare the Effect of Eprosartan and Eprosartan Mesylate on Blood Pressure in Subjects with Essential Hypertension
• Description: Teveten was launched in Germany for the treatment of hypertension. There are several ways in which it has been prepared, the shortest of which is four steps; beginning with displacement of 2-butyl-4-chloroimidazole-5-carboxaldehyde with methyl 4-(bromomethyl)benzoate. Teveten is an angiotensin Ⅱ antagonist selective for the AT, subtype receptor. It is a potent, highly selective, competitve antagonist with no agonist activity. Duration of action is similar to Enalapril (greater than 12 hr) but Teveten had a faster onset. While it is orally active, it rapidly dissociates from the receptor. This is contrary to its prolonged duration of action, which presumably results from slow removal from compartments within tissue, cells or matrix around the AT, receptor. It is not bound by BSA.
• Uses: Prototype of the imidazoleacrylic acid angiotensin II receptor antagonists. Antihypertensive Eprosartan (E590100) impurity. Eprosartan is a prototype of the imidazoleacrylic acid angiotensin II receptor antagonists. Eprosartan is an antihypertensive.
• 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.

Technology Process of Eprosartan

There total 30 articles about Eprosartan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

methyl (E)-3-<2-butyl-1-<(4-carbomethoxyphenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenoate (133040-06-9) → eprosartan (133040-01-4,148674-39-9)

Guidance literature:

With potassium hydroxide; In ethanol;

DOI:10.1021/jm00108a043

Reference yield: 70.92%

2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde (133040-03-6) + 3-ethoxy-3-oxo-2-(thien-3-ylmethyl)propanoic acid (143468-96-6) → eprosartan (133040-01-4,148674-39-9)

Guidance literature:

2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde; 3-ethoxy-3-oxo-2-(thien-3-ylmethyl)propanoic acid; With piperidine; hydrogenchloride; In di-isopropyl ether; water; at 40 - 55 ℃; under 760.051 Torr; Heating / reflux;

With water; sodium hydroxide; In methanol; for 3h; Heating / reflux;

With hydrogenchloride; In methanol; water; at 35 - 40 ℃; pH=5.0 - 5.2;

Reference yield: 68.0%

eprosartan mesylate → eprosartan (133040-01-4,148674-39-9)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; pH=2;

DOI:10.1021/acs.cgd.6b01588

upstream raw materials:

methyl (E)-3-<2-butyl-1-<(4-carbomethoxyphenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenoate

4-[5-(1-Acetoxy-2-methoxycarbonyl-3-thiophen-2-yl-propyl)-2-butyl-imidazol-1-ylmethyl]-benzoic acid methyl ester

2-butyl-1H-imidazole

Methyl 4-(bromomethyl)benzoate

Downstream raw materials:

SB 206328

4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzonitrile

(E)-3-<2-butyl-1-<(4-carboxamidophenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenamide

(E)-α-[[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-2-thiophene propanoic acid acetate

Refernces

• 1、 Khare, Sawani G.,Jena, Sunil K.,Sangamwar, Abhay T.,Khullar, Sadhika,Mandal, Sanjay K.. "Multicomponent Pharmaceutical Adducts of α-Eprosartan: Physicochemical Properties and Pharmacokinetic Study". . p. 1589 - 1599. Retrieved 2017/04/11.
• 2、 -. "PROCESS FOR EPROSARTAN INTERMEDIATE". . . Retrieved 2011/04/14.