727718-93-6

Basic information

• Product Name: 2-butyl-4-chloro-5-(azidomethyl)-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4yl)methyl]-1H-imidazole
• Synonyms: 2-butyl-4-chloro-5-(azidomethyl)-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4yl)methyl]-1H-imidazole
• CAS NO: 727718-93-6
• Molecular Weight: 447.93
• Mol File: 727718-93-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: >139°C (dec.)
• CAS DataBase Reference: 2-butyl-4-chloro-5-(azidomethyl)-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4yl)methyl]-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-butyl-4-chloro-5-(azidomethyl)-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4yl)methyl]-1H-imidazole(727718-93-6)
• EPA Substance Registry System: 2-butyl-4-chloro-5-(azidomethyl)-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4yl)methyl]-1H-imidazole(727718-93-6)

Safety Data

• Hazardous Substances Data: 727718-93-6(Hazardous Substances Data)

Usage

Description

Losartan is a medication used to treat high blood pressure. It is also used for diabetic kidney disease, heart failure, and left ventricular enlargement.Losartan was patented in 1986, and approved for medical use in the United States in 1995. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.Losartan was the first nonpeptide imidazole to beintroduced as an orally active angiotensin II antagonist withhigh specificity for AT1. When administered to patients, itundergoes extensive first-pass metabolism, with the 5-methanol being oxidized to a carboxylic acid. This metabolismis mediated by CYP 2C9 and 3A4 isozymes. The 5-methanol metabolite is approximately 15 times more potentthan the parent hydroxyl compound. Because the parent hydroxylcompound has affinity for the AT1 receptor, strictlyspeaking, it is not a prodrug.

Uses

Losartan Azide is an impurity of Losartan (L470470). Losartan is a nonpeptide angiotensin II AT1-receptor antagonist. Antihypertensive.

Upstream product

• 114798-26-4 lorsartan 
• 124750-99-8 cozaar 
• 124751-00-4 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol 

Downstream Products

• 141949-89-5 C₂₂H₂₄ClN₇ 
• 848830-23-9 C₆₃H₆₆ClN₉O₁₃S₄ 

Relevant articles and documents

Synthesis and evaluation of [18F]FETLOs and [18F]AMBF3LOS as novel 18F-labelled losartan derivatives for molecular imaging of angiotensin II type 1 receptors

Losartan is widely used in clinics to treat cardiovascular related diseases by selectively blocking the angiotensin II type 1 receptors (AT1Rs), which regulate the renin-angiotensin system (RAS). Therefore, monitoring the physiological and pathological biodistribution of AT1R using positron emission tomography (PET) might be a valuable tool to assess the functionality of RAS. Herein, we describe the synthesis and characterization of two novel losartan derivatives PET tracers, [18F]fluoroethyl-losartan ([18F]FEtLos) and [18F]ammoniomethyltrifluoroborate-losartan ([18F]AMBF3Los). [18F]FEtLos was radiolabeled by 18F-fluoroalkylation of losartan potassium using the prosthetic group 2-[18F]fluoroethyl tosylate; whereas [18F]AMBF3Los was prepared following an one-step 18F-19F isotopic exchange reaction, in an overall yield of 2.7 ± 0.9% and 11 ± 4%, respectively, with high radiochemical purity (>95%). Binding competition assays in AT1R-expressing membranes showed that AMBF3Los presented an almost equivalent binding affinity (Ki 7.9 nM) as the cold reference Losartan (Ki 1.5 nM), unlike FEtLos (Ki 2000 nM). In vitro and in vivo assays showed that [18F]AMBF3Los displayed a good binding affinity for AT1R-overexpressing CHO cells and was able to specifically bind to renal AT1R. Hence, our data demonstrate [18F]AMBF3Los as a new tool for PET imaging of AT1R with possible applications for the diagnosis of cardiovascular, inflammatory and cancer diseases.