Chlorcyclizine hydrochloride

• CAS: 14362-31-3
• Catalog Number: ACM14362313
• Category: Main Products
• Molecular Weight: 337.29
• Molecular Formula: C₁₈H₂₂Cl₂N₂
• Synonyms: 1-(p-chloro-alpha-phenylbenzyl)-4-methylpiperazinehydrochloride;1-(p-chloro-alpha-phenylbenzyl)-4-methyl-piperazinhydrochloride;1-(p-chlorobenzhydryl)-4-methylpiperazinehydrochloride;chlorcycliziniumchloride;di-paralene;eramide;1-[(4-CHLOROPHENYL)PHENYL-METHYL]-4-METHYLPIPERAZINE HYDROCHLORIDE;CHLORCYCLIZINE HCL
• IUPAC Name: 1-[(4-chlorophenyl)-phenylmethyl]-4-methylpiperazine;hydrochloride
• Canonical SMILES: CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl.Cl
• InChI Key: MSIJLVMSKDXAQN-UHFFFAOYSA-N
• Boiling Point: 393.6ºC at 760mmHg
• Flash Point: 191.9ºC
• Density: 1.145g/cm³
• Appearance: solid
• EC Number: 238-335-1
• Exact Mass: 336.11600
• Hazard Statements: T
• Safety Description: 53-22-36/37/39-45
• Supplemental Hazard Statements: H301-H315-H319-H335
• Symbol: GHS06

Case Study

Repurposing the Antihistamine Chlorcyclizine to Treat Hepatitis C Virus Infection

He, Shanshan, et al. Science translational medicine, 2015, 7(282), 282ra49-282ra49.

Chlorcyclizine hydrochloride (CCZ), an over-the-counter drug used to treat allergic symptoms, was demonstrated in this work to be a potent inhibitor of hepatitis C virus (HCV) infection. Further in vivo studies in mice transplanted with primary human hepatocytes confirmed its efficacy in restricting genotype 1b and 2a HCV infection.
Anti-HCV activities of Chlorcyclizine HCl
· On Huh7.5.1 cells, racemic (R)- and (S)-CCZ were compared with wild-type cell culture-induced HCV infection (HCVcc; genotype 2a, JFH-1 strain) of the same strain. The intracellular and extracellular viral RNA was significantly lower when we administered racemic, (R)-, and (S)-CCZ as opposed to DMSO. These findings further showed that the anti-HCV action of CCZ analogs is configuration independent. But (S)-CCZ exhibited a weaker inhibitory effect on histamine receptors than (R)-CCZ, prompting the selection of (S)-CCZ for additional analysis.
· (S)-CCZ reduced intracellular HCV RNA levels in wild-type HCVcc-infected primary human liver cells dose-dependently. When Huh7.5.1 cells were infected with HCV chimeric genotype viruses, extracellular HCV RNA and infectivity [median tissue culture infectious dose per milliliter (TCID50/ml)] were inhibited by (S)-CCZ (10 mM) which indicates pan-genotypic activity. Additionally, (S)-CCZ was shown to be non-cytotoxic at concentrations of 1.0 and 5.0 mM, with only low cytotoxicity observed at 10 mM in Huh7.5.1 cells following continuous treatment for 21 days.

Study of the Permeability of Chlorpheniramine and Chlorcyclizine Through the Olfactory Mucosa

Kandimalla, Karunya K., et al. Journal of pharmaceutical sciences, 2005, 94(3), 613-624.

Chlorcyclizine and chlorpheniramine are antihistamines with similar structures. This in vitro study investigated permeability of chlorpheniramine and chlorcyclizine across the bovine olfactory mucosa to determine the biological and physicochemical mechanisms underlying the limited exposure of the central nervous system to these compounds after nasal administration.
· Chlorcyclizine and chlorpheniramine submucosal to mucosal fluxes (Js-m) across the olfactory mucosa were vastly higher than mucosal to submucosal fluxes (Jm-s).
· In addition, both compounds' submucosal-mucosal permeability was temperature-dependent and saturable.
· In the presence of metabolic inhibitors (ouabain and 2,4dinitrophenol) and Pglycoprotein (Pgp)/multidrug resistance protein 1 (MRP1) inhibitors (quinidine and verapamil), Jm-s jumped up, and Js-m dropped. These findings reveal that chlorpheniramine and chlorcyclizine are evacuated from the nose by efflux transporters like Pgp and MRP1.
· Transport experiments with inert polymeric membranes showed that chlorpheniramine and chlorcyclizine had reduced permeability at donor concentrations greater than 3 mM, indicating that physicochemical factors such as self-aggregation may also contribute to the decreased olfactory mucosal permeability of these compounds at higher concentrations.

Custom Q&A

What is the molecular formula of Chlorcyclizine hydrochloride?

The molecular formula of Chlorcyclizine hydrochloride is C18H22Cl2N2.

What are some synonyms for Chlorcyclizine hydrochloride?

Some synonyms for Chlorcyclizine hydrochloride include Histantin, Perazil, Eramide, and ChlorCyclizine-d4Hydrochloride.

What is the chemical structure of Chlorcyclizine hydrochloride?

The chemical structure of Chlorcyclizine hydrochloride is shown in the referenced images.

What is the CAS number for Chlorcyclizine hydrochloride?

The CAS number for Chlorcyclizine hydrochloride is 1620-21-9.

Is Chlorcyclizine hydrochloride considered toxic?

The reference does not provide information on the toxicity of Chlorcyclizine hydrochloride.

What is the UNII number for Chlorcyclizine hydrochloride?

The UNII number for Chlorcyclizine hydrochloride is NPB7A7874U.

What is the IUPAC name for Chlorcyclizine hydrochloride?

The IUPAC name for Chlorcyclizine hydrochloride is 1-((4-Chlorophenyl)(phenyl)methyl)-4-methylpiperazine hydrochloride.

What is the EINECS number for Chlorcyclizine hydrochloride?

The EINECS number for Chlorcyclizine hydrochloride is 238-335-1.

Does Chlorcyclizine hydrochloride have any pharmacological uses?

The reference does not provide information on the pharmacological uses of Chlorcyclizine hydrochloride.

What are some other names for Chlorcyclizine hydrochloride in different databases?

Some other names for Chlorcyclizine hydrochloride in different databases include CHEMBL1889091, DTXCID5025360, and NSC756678.