Chlorcyclizine - CAS 82-93-9
Catalog number: 82-93-9
Category: Inhibitor
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Molecular Formula:
C18H21ClN2
Molecular Weight:
300.83
COA:
Inquire
Targets:
Histamine Receptor
Description:
Chlorcyclizine is a first-generation Histamine Receptor antagonist of the phenylpiperazine class. It can be used primarily to treat allergy symptoms such as rhinitis, urticaria, and pruritus, and may also be used as an antiemetic. Chlorcyclizine also has some anticholinergic, antiserotonergic, and local anesthetic properties. It also has been studied as a potential treatment for hepatitis C.
Purity:
98%
Appearance:
yellow to orange oil
Synonyms:
1-[(4-Chlorophenyl)(phenyl)methyl]-4-methylpiperazine, 1-[(4-Chlorophenyl)phenylmethyl]-4-methyl-piperazine; 1620-21-9 (HCl salt); Di-Paralene; Mantadil; Pruresidine; Trihistan;
Solubility:
Soluble in DMSO
Storage:
-20℃ Freezer
MSDS:
Inquire
Application:
allergy symptoms
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
InChIKey:
WFNAKBGANONZEQ-UHFFFAOYSA-N
InChI:
InChI=1S/C18H21ClN2/c1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16/h2-10,18H,11-14H2,1H3
Canonical SMILES:
CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl
1.Enantiomeric quality control of antihistamines in pharmaceuticals by affinity electrokinetic chromatography with human serum albumin as chiral selector.
Martínez-Gómez MA1, Sagrado S, Villanueva-Camañas RM, Medina-Hernández MJ. Anal Chim Acta. 2007 Jun 5;592(2):202-9. Epub 2007 Apr 21.
The present paper deals with the enantiomeric separation of six antihistaminic enantiomers by affinity electrokinetic chromatography (AEKC)-partial filling technique using human serum albumin (HSA) as chiral selector. A multivariate optimization approach of the most critical experimental variables in enantioresolution, running pH, HSA concentration and HSA plug length (SPL) was carried out since there are interactions between variables that could not be considered in an univariate optimization. The estimated and experimental resolution values obtained for antihistaminic enantiomers varied from 1.13 (for orphenadrine) to 2.15 (for brompheniramine). The optimum experimental conditions for enantioresolution of each compound were: brompheniramine, pH 8.5, [HSA] 180 microM, SPL 180 s; chlorcyclizine, pH 6.5, [HSA] 180 microM, SPL 150 s; chlorpheniramine, pH 8.25, [HSA] 160 microM, SPL 150 s; hydroxyzine, pH 7.0, [HSA] 180 microM, SPL 150 s; and orphenadrine, pH 7.
2.Discovery, Optimization, and Characterization of Novel Chlorcyclizine Derivatives for the Treatment of Hepatitis C Virus Infection.
He S1, Xiao J2, Dulcey AE2, Lin B1, Rolt A2, Hu Z1, Hu X2, Wang AQ2, Xu X2, Southall N2, Ferrer M2, Zheng W2, Liang TJ1, Marugan JJ2. J Med Chem. 2016 Feb 11;59(3):841-53. doi: 10.1021/acs.jmedchem.5b00752. Epub 2016 Feb 1.
Recently, we reported that chlorcyclizine (CCZ, Rac-2), an over-the-counter antihistamine piperazine drug, possesses in vitro and in vivo activity against hepatitis C virus. Here, we describe structure-activity relationship (SAR) efforts that resulted in the optimization of novel chlorcyclizine derivatives as anti-HCV agents. Several compounds exhibited EC50 values below 10 nM against HCV infection, cytotoxicity selectivity indices above 2000, and showed improved in vivo pharmacokinetic properties. The optimized molecules can serve as lead preclinical candidates for the treatment of hepatitis C virus infection and as probes to study hepatitis C virus pathogenesis and host-virus interaction.
3.Pronounced inhibitory effect of chlorcyclizine (CCZ) in experimental hepatocarcinoma.
Dastidar SG1, Ganguly K, Mahapatra SK, Dutta NK, Mazumdar K, Chakrabarty AN, Motohashi N. In Vivo. 2006 Jan-Feb;20(1):97-102.
Thepiperazine chlorcyclizine HCl (CCZ), possessing significant antimetabolic as well as virucidal and virustatic activities against the human immunodeficiency virus (HIV) and other retroviruses, was selected to determine its anticarcinogenic potential The anticancer activity of CCZ was evaluated against procarcinogen n-diethylnitrosamine (NDA)-initiated hepatocarcinogenesis, which was subsequently promoted by phenobarbital (PB) in male Sprague-Dawley rats. The anticancer efficacy of CCZ was monitored by estimating some potential markers of neoplastic and preneoplastic hepatic conditions, e.g., glutathione (GSH), glutathione-S-transferase (GST) and gamma-glutamyl transpeptidase (gammaGTP). CCZ exhibited antineoplastic activity on a long-term therapeutic basis. Furthermore, this drug restricted the exponential increase of the antioxidant markers in the hyperplastic nodule and the surrounding liver tissues in comparison with the carcinogen-controlled rats during the entire period of treatment.
4.Effects of the histamine H1 antagonist chlorcyclizine on rat fetal palate development.
Enright BP1, Gu YZ, Snyder RD, Dugyala RR, Obert LA, Treinen KA, McIntyre BS, Veneziale RW. Birth Defects Res B Dev Reprod Toxicol. 2010 Dec;89(6):474-84. doi: 10.1002/bdrb.20261.
BACKGROUND: The effects of histamine H1 antagonist chlorcyclizine on rat palate development were characterized following in utero exposure.
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Chemical Structure

CAS 82-93-9 Chlorcyclizine

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