740747-71-1

Basic information

• Product Name: (R)-1-(1-phenylethyl)-1H-imidazole-5-carbonyl chloride
• Synonyms: (R)-1-(1-phenylethyl)-1H-imidazole-5-carbonyl chloride
• CAS NO: 740747-71-1
• Molecular Weight: 234.685
• Mol File: 740747-71-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-1-(1-phenylethyl)-1H-imidazole-5-carbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(1-phenylethyl)-1H-imidazole-5-carbonyl chloride(740747-71-1)
• EPA Substance Registry System: (R)-1-(1-phenylethyl)-1H-imidazole-5-carbonyl chloride(740747-71-1)

Safety Data

• Hazardous Substances Data: 740747-71-1(Hazardous Substances Data)

Upstream product

• 53188-20-8 Etomidate hydrochloride 
• 33125-97-2 etomidate 
• 56649-48-0 (R)-(+)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid 

Downstream Products

• 1016274-83-1 C₁₄H₁₇N₃O₂ 
• 1016274-81-9 C₁₃H₁₅N₃O 

Relevant articles and documents

Metabolite-inactive etomidate analogues alleviating suppression on adrenal function in Beagle dogs

Owing to rapid generation in body, the metabolites of etomidate softdrug are able to accumulate in either the brain or periphery and subsequently affect the recovery from anaesthesia or cause corticosteroid suppression. This study was designed to investigate the ability of two etomidate analogues (ET-26, ET-42) with inactive metabolites to provide anaesthesia with lesser corticosteroid suppression. The 50% effective dose (ED50) of ET-26, ET-42, Etomidate, MOC-ET (an etomidate softdrug) and CPMM (an improved etomidate softdrug) required to induce anaesthesia intravenously in Beagle dogs were 1.44 mg/kg, 0.72 mg/kg, 0.43 mg/kg 23.12 mg/kg and 0.59 mg/kg, respectively. After adrenocorticotropic hormone (ACTH) stimulation, the serum concentrations of cortisol and corticosterone in the ET-26, ET-42 and CPMM groups were similar to those of controls, and significantly higher than those of the etomidate and MOC-etomidate groups (P 50 = 1.44 mg/kg) and ET-42 (ED50 = 0.72 mg/kg) were determined. Both analogues can significantly reduce the corticosteroid suppression in vivo. Metabolite-inactive etomidate derivatives with slow metabolism might provide a novel strategy to improve Etomidate associated corticosteroid suppression.

Anesthetic compounds and related methods of use

Provided herein are compounds according to formula (I): Provided herein is also a pharmaceutical composition comprising a compound according to formula (I) and a pharmaceutically acceptable carrier, and a method for providing anesthesia in a subject by administering such a pharmaceutical composition.

New selective inhibitors of steroid 11β-hydroxylation in the adrenal cortex. Synthesis and structure-activity relationship of potent etomidate analogues

Derivatives of etomidate were evaluated as inhibitors of adrenal steroid 11β-hydroxylations. Stereoselective coupling by Mitsunobu produced chirally pure analogues to study the effect of configuration, modification of the ester, and substitution in the phenyl ring, with the aim to probe specific sites for introducing a radionuclide. Iodophenyl metomidate (IMTO) labeled with iodine-131 served as radioligand for structure-affinity relationship studies. We have characterized the kinetic parameters of specific 131I-IMTO binding on rat adrenal membranes and used the displacement of 131I-IMTO binding to evaluate functionalized MTO analogues. Our results indicated that (1) (R)-configuration is essential for high affinity, (2) highest potency resides in the ethyl, 2-propyl, and 2-fluoroethyl esters, and (3) substitution of the phenyl ring is well tolerated. The clinically used inhibitors metyrapone and ketoconazole inhibited 131I-IMTO binding with low affinity. Incubation of selected analogues with human adrenocortical NCI-h295 cells demonstrated a high correlation with the inhibitory effect on cortisol secretion.