Clemizole - CAS 442-52-4
Catalog number: 442-52-4
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C19H20ClN3
Molecular Weight:
325.8350
COA:
Inquire
Targets:
Histamine Receptor
Description:
Clemizole is an H1 antagonist acts as a TRPC5 channel blocker (IC50 values are 1.1, 6.4, 9.1, 11.3 and 26.5 μM for TRPC5, TRPC4, TRPC3, TRPC6 and TRPC7 respectively).
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Purity:
≥95%
Appearance:
White solid
Synonyms:
1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
TRPC5 channel blocker
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Milligrams-Grams
Boiling Point:
506.1ºC at 760mmHg
Density:
1.25 g/cm3
InChIKey:
CJXAEXPPLWQRFR-UHFFFAOYSA-N
InChI:
InChI=1S/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
Canonical SMILES:
C1CCN(C1)CC2=NC3=CC=CC=C3N2CC4=CC=C(C=C4)Cl
Current Developer:
Eiger BioPharmaceuticals, Inc.
1.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 posit
Vlahakis JZ1, Vukomanovic D, Nakatsu K, Szarek WA. Bioorg Med Chem. 2013 Nov 1;21(21):6788-95. doi: 10.1016/j.bmc.2013.07.050. Epub 2013 Aug 8.
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 selective for the HO-2 isozyme (constitutive), and had substantially less inhibitory activity on the HO-1 isozyme (inducible). The compounds represent the first report of highly potent and selective inhibitors of HO-2 activity, and complement our suite of selective HO-1 inhibitors. The study has revealed many candidates based on the inhibition of heme oxygenases for potentially useful pharmacological and therapeutic applications.
2.Using chimeric mice with humanized livers to predict human drug metabolism and a drug-drug interaction.
Nishimura T1, 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. J Pharmacol Exp Ther. 2013 Feb;344(2):388-96. doi: 10.1124/jpet.112.198697. Epub 2012 Nov 8.
Interspecies differences in drug metabolism have made it difficult to use preclinical animal testing data to predict the drug metabolites or potential drug-drug interactions (DDIs) that will occur in humans. Although chimeric mice with humanized livers can produce known human metabolites for test substrates, we do not know whether chimeric mice can be used to prospectively predict human drug metabolism or a possible DDI. Therefore, we investigated whether they could provide a more predictive assessment for clemizole, a drug in clinical development for the treatment of hepatitis C virus (HCV) infection. Our results demonstrate, for the first time, that analyses performed in chimeric mice can correctly identify the predominant human drug metabolite before human testing. The differences in the rodent and human pathways for clemizole metabolism were of importance, because the predominant human metabolite was found to have synergistic anti-HCV activity.
3.[Syphilis treatment. German and international guidelines--a comparison].
Schöfer H1. Hautarzt. 2005 Feb;56(2):141-50.
Guidelines are an important instrument for improving the quality of medical care. In 2001, the German STD Society (DSTDG) published guidelines for syphilis diagnostics and treatment. For two reasons, these guidelines had to be reviewed urgently: Firstly, there is an obvious "renaissance" of syphilis among men having sex with men, which is complicated by a frequent comorbidity with HIV infection. Secondly, the standard drug for syphilis treatment in Germany, clemizole penicillin, has no longer been available since July 2003. In this article, the new German guidelines for syphilis treatment 2004, published by the DSTDG, are compared with other syphilis guidelines, which are valid for the European countries, i.e., the CDC, UK, Russian, and European guidelines 2002.
4.Clemizole hydrochloride is a novel and potent inhibitor of transient receptor potential channel TRPC5.
Richter JM1, Schaefer M1, Hill K2. Mol Pharmacol. 2014 Nov;86(5):514-21. doi: 10.1124/mol.114.093229. Epub 2014 Aug 19.
Canonical transient receptor potential channel 5 (TRPC5) is a nonselective, Ca(2+)-permeable cation channel that belongs to the large family of transient receptor potential channels. It is predominantly found in the central nervous system with a high expression density in the hippocampus, the amygdala, and the frontal cortex. Several studies confirm that TRPC5 channels are implicated in the regulation of neurite length and growth cone morphology. We identified clemizole as a novel inhibitor of TRPC5 channels. Clemizole efficiently blocks TRPC5 currents and Ca(2+) entry in the low micromolar range (IC50 = 1.0-1.3 µM), as determined by fluorometric intracellular free Ca(2+) concentration ([Ca(2+)]i) measurements and patch-clamp recordings. Clemizole blocks TRPC5 currents irrespectively of the mode of activation, for example, stimulation of G protein-coupled receptors, hypo-osmotic buffer conditions, or by the direct activator riluzole. Electrophysiological whole-cell recordings revealed that the block was mostly reversible.
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CAS 442-52-4 Clemizole

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