Clemizole hydrochloride

Category	HCV Protease
CAS	1163-36-6
Description	The hydrochloride salt form of clemizole, which is a histamine H1 antagonist with antitumor activity. It also has hepatitis C antiviral effect through restraining NS4B function and could also be used as an anticonvulsant in zebrafish Dravet syndrome model.

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Product Information

Synonyms	Allercur; Clemizole HCl; Clemizole (hydrochloride); Reactrol; 1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole hydrochloride
IUPAC Name	1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole;hydrochloride
Molecular Weight	362.30
Molecular Formula	C19H20ClN3.HCl
Canonical SMILES	C1CCN(C1)CC2=NC3=CC=CC=C3N2CC4=CC=C(C=C4)Cl.Cl
InChI	InChI=1S/C19H20ClN3.ClH/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;1H
InChIKey	DNFMJYXRIMLMBZ-UHFFFAOYSA-N
Boiling Point	506.1°C at 760 mmHg
Melting Point	241 °C
Flash Point	259.9°C
Purity	95%
Density	1.25 g/cm3
Solubility	DMSO: ≥ 3.6 mg/mL
Appearance	Solid Powder
Shelf Life	2 years
Storage	-20°C Freeze
Complexity	377
Exact Mass	361.1112531
In Vitro	Clemizole hydrochloride is found to inhibit HCV RNA replication in cell culture that is mediated by its suppression of NS4B's RNA binding, with little toxicity for the host cell. The EC50 of Clemizole on the W55R mutant J6/JFH RNA is ~18 µM (2.25 times the EC50 of the wild-type RNA). Clemizole is a novel inhibitor of TRPC5 channels. Clemizole efficiently blocks TRPC5 currents and Ca2+ entry in the low micromolar range (IC50=1.0-1.3 µM). Clemizole exhibits a six-fold selectivity for TRPC5 over TRPC4β (IC50=6.4 µM), the closest structural relative of TRPC5, and an almost 10-fold selectivity over TRPC3 (IC50=9.1 µM) and TRPC6 (IC50=11.3 µM). Clemizole hydrochloride as a novel blocker of TRPC5 with a half-maximal inhibitory concentration of 1.1 µM. The concentration-response curves confirmed a concentration-dependent block of TRPC5 by Clemizole and revealed an apparent IC50 of 1.1±0.04 µM.
In Vivo	Clemizole hydrochloride has an unexpectedly short plasma half-life (measured at 0.15 hours); it is very rapidly biotransformed into a glucuronide (M14) and a dealkylated metabolite (M12) and into a variety of lesser metabolites in C57BL/6J mice.
PSA	21.06000
Target	Histamine Receptor; TRP Channel; HCV Protease; HCV
Vapor Pressure	2.29E-10mmHg at 25°C