| Identification | More | [Name]
Clemizole hydrochloride | [CAS]
1163-36-6 | [Synonyms]
1-[(4-Chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzoimidazole hydrochloride
1-P-CHLOROBENZYL-2-[1-PYRROLIDINYL]-METHYLBENZIMIDAZOLE HYDROCHLORIDE
CLEMIZOLE HCL
CLEMIZOLE HYDROCHLORIDE
LABOTEST-BB LT00453174
1-(p-chlorobenzil)-2-pirrolidil-metil-benzimidazolocloridato
1-(p-chlorobenzyl)-2-(1-pyrrolidinylmethyl)-benzimidazolmonohydrochloride
1-p-chlorobenzyl-pyrrolidyl-methylene-benzimidazolehydrochloride
allercur
allercurehydrochloride
p48
1-(4-Chlorophenyl)methyl)-2-(1-pyrrolidinylmethyl)-(1H)-benzimidazoleHCl
1-(P-CHLOROBENZYL)-2-(1-PYRROLIDINYLMETHYL)-BENZIMIDAZOL | [EINECS(EC#)]
214-605-4 | [Molecular Formula]
C19H21Cl2N3 | [MDL Number]
MFCD00051435 | [Molecular Weight]
362.3 | [MOL File]
1163-36-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
239-241° | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
H2O: soluble2mg/mL, clear (warmed) | [form ]
powder | [color ]
white to beige | [Water Solubility ]
16.84mg/L at 25℃ | [Merck ]
13,2368 | [InChIKey]
DNFMJYXRIMLMBZ-UHFFFAOYSA-N | [LogP]
1.99 | [CAS DataBase Reference]
1163-36-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
DD6730000
| [HS Code ]
2933.99.8290 |
| Hazard Information | Back Directory | [Originator]
Allercur,Roerig,US,1960 | [Uses]
Clemizole is an antihistamine that antagonizes the histamine 1 receptor at high nanomolar concentrations. It less potently blocks transient receptor potential canonical channel 5 (TRPC5; IC50 = 1.0-1.3 μM), with at least 6-fold selectivity for TRPC5 over other TRP channels. Clemizole also has hepatitis C antiviral action through inhibition of NS4B function, showing synergy with boceprevir , and it inhibits seizures in a zebrafish model of Dravet Syndrome. | [Definition]
ChEBI:Clemizole hydrochloride is a member of benzimidazoles. | [Manufacturing Process]
From 13.1 g of N-p-chlorobenzyl-2-nitroaniline (MP 110°C, obtained in the
form of orange-red needles, from o-nitrochlorobenzene and pchlorobenzylamine by reaction for 3 hours at 150°C) by reduction with Raneynickel and hydrogen, in which reaction the substance may be suspended in
methanol or dissolved in methanol-ethyl acetate at normal pressure and at
about 40°C with combination of the theoretical quantity of hydrogen, 12.2 g
are obtained of o-amino-N-p-chlorobenzylaniline, which after recrystallization
from aqueous methanol has a MP of 90°C.
8 g of o-amino-N-p-chlorobenzylaniline and 2.8 g of pyridine are dissolved in
dry ether and reacted with an ethereal solution of 3.9 g of chloracetyl chloride
with cooling in a mixture of ice and common salt. 8 g of N-p-chlorobenzyl-N'-
chloracetyl-o-phenylene diamine are obtained which can be worked up in the
form of the crude product and, in the slightly colored form, has a MP of
130°C.
7.6 g of this compound are boiled with 3.9 g of pyrrolidine in 70 cc of toluene
for some hours under reflux. After extraction by shaking with water and
treatment with hydrochloric acid the hydrochloride is produced of N-pchlorobenzyl-N'-pyrrolidylacetyl-o-phenylene diamine together with some 1-pchlorobenzyl-2-N-pyrrolidylmethyl-benzimidazole. The former, after
recrystallization from butanol, melts with foaming at 205°C, the latter, after
recrystallization from butanol melts at 239°C to 241°C, and is in the form of
white microscopic rods. Boiling in nitrobenzene converts the former compound
into the latter. | [Therapeutic Function]
Antihistaminic | [Biological Activity]
(ns4b)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 vitro]
although significant, clemizole’s antiviral effect was moderate (50% effective concentration of 8 mm against a hcv genotype 2a clone). clemizole’s antiviral effect was highly synergistic with the hcv protease inhibitors vx950 and sch503034, without toxicity. in contrast, clemizole combinations with either interferon, ribavirin, or the nucleoside (nm283) and nonnucleoside (hcv796) hcv polymerase inhibitors were additive [1]. | [in vivo]
clemizole had an unexpectedly short plasma half-life; it was very rapidly bio-transformed into a glucuronide (m14) and a dealkylated metabolite (m12) and into a variety of lesser metabolites in c57bl/6j mice [2]. | [IC 50]
8 mm | [storage]
Store at -20°C | [References]
[1] einav s, sobol hd, gehrig e, glenn js. the hepatitis c virus (hcv) ns4b rna binding inhibitor clemizole is highly synergistic with hcv protease inhibitors. j infect dis. 2010;202(1):65-74.
[2] nishimura t, hu y, wu m, pham e, suemizu h, elazar m, liu m, idilman r, yurdaydin c, angus p, stedman c, murphy b, glenn j, nakamura m, nomura t, chen y, zheng m, fitch wl, peltz g. using chimeric mice with humanized livers to predict human drug metabolism and a drug-drug interaction. j pharmacol exp ther. 2013;344(2):388-96. doi: 10.1124/jpet.112.198697. epub 2012 nov 8. |
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