442-52-4

Basic information

• Product Name: Clemizole
• Synonyms: 1-p-Chlorobenzyl-2-[1-pyrrolidinylmethyl] benzimidazole;1-(p-Chlorobenzyl)-2-pyrrolidylmethylenebenzimidazole;1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-1H-benzimidazole (Clemizole);1-(4-Chlorobenzyl)-2-(pyrrolizinomethyl)-1H-benzimidazole;1-(p-Chlorobenzyl)-2-(1-pyrrolidinylmethyl)-1H-benzimidazole;Histacur;1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)benzimidazole;1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole
• CAS NO: 442-52-4
• Molecular Formula: C₁₉H₂₀ClN₃
• Molecular Weight: 325.8352
• EINECS: 207-133-5
• Product Categories: API intermediates;Inhibitors
• Mol File: 442-52-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 239-241℃
• Boiling Point: 506.1°Cat760mmHg
• Flash Point: 259.9°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 2.29E-10mmHg at 25°C
• Refractive Index: 1.655
• Solubility: insoluble in H2O; ≥16.2 mg/mL in DMSO; ≥95.8 mg/mL in EtOH
• CAS DataBase Reference: Clemizole(CAS DataBase Reference)
• NIST Chemistry Reference: Clemizole(442-52-4)
• EPA Substance Registry System: Clemizole(442-52-4)

Safety Data

• Hazardous Substances Data: 442-52-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a pyrrolidin-1-ylmethyl and a 4-chlorobenzyl groups at positions 2 and 1 respectively.

Therapeutic Function

Antihistaminic

Biological Activity

the ns4b protein is a key player in hcv replication. disrupting ns4b function thus represents an attractive new anti-hcv strategy. combining clemizole with other anti-hcv agents could increase the antiviral effect achieved with 1 active drug alone and decrease emergence of viral resistance.

in vivo

clemizole had an unexpectedly short plasma half-life; it was very rapidly biotransformed into a glucuronide (m14) and a dealkylated metabolite (m12) and into a variety of lesser metabolites in c57bl/6j mice [2].

InChI:InChI=1/C19H20ClN3/c20-16-9-7-15(8-10-16)13-23-18-6-2-1-5-17(18)21-19(23)14-22-11-3-4-12-22/h1-2,5-10H,3-4,11-14H2

Upstream product

• 7152-24-1 2-methylsulfanylbenzimidazole 
• 134469-07-1 Benzimidazol-2-thiol 
• 57159-81-6 2-(methylsulfonyl)-1H-benzo[d]imidazole 
• 54600-29-2 1-((trimethylsilyl)methyl)pyrrolidine 
• 15784-37-9 2-methyl-1-(phenylsulfonyl)-1H-benzo[d]imidazole 
• 88-73-3 2-Chloronitrobenzene 
• 104-86-9 4-chlorobenzylamine 
• 5729-18-0 N-(p-Chlorophenylmethyl)-2-amino aniline 
• 5822-16-2 N-(p-Chlorobenzyl)-2-nitro aniline 
• 622-95-7 4-chlorobenzyl bromide 
• 718634-79-8 pyrrolidino-acetic acid-[2-(4-chloro-benzylamino)-anilide] 
• 109037-60-7 pyrrolidino-acetic acid-[2-(4-chloro-benzylidenamino)-anilide] 
• 123-75-1 pyrrolidine 
• 7189-18-6 1-(4-chlorobenzyl)-2-(chloromethyl)-1H-benzo[d]imidazole 

Downstream Products

• 1163-36-6 clemizole hydrochloride 
• 1251554-58-1 1-(4-chlorobenzyl)-2-(d2-(pyrrolidin-1-yl)methyl)-1H-benzo[d]imidazole 

Relevant articles and documents

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.

Selective inhibition of heme oxygenase-2 activity by analogs of 1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole (clemizole): Exploration of the effects of substituents at the N-1 position

Several analogs based on the lead structure of 1-(4-chlorobenzyl)-2- (pyrrolidin-1-ylmethyl)-1H-benzimidazole (clemizole) were synthesized and evaluated as novel inhibitors of heme oxygenase (HO). Many of the compounds were found to be potent and highly s