Identification
- Brand Names
- Ahist Antihistamine, Biclora, Bonine for Kids, Stahist Ad Liquid
- Generic Name
- Chlorcyclizine
- DrugBank Accession Number
- DB08936
- Background
Chlorcyclizine is a first generation phenylpiperazine class antihistamine used to treat urticaria, rhinitis, pruritus, and other allergy symptoms. Chlorcyclizine also has some local anesthetic, anticholinergic, and antiserotonergic properties, and can be used as an antiemetic.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Chlorcyclizine (DB08936)
- Weight
- Average: 300.826
Monoisotopic: 300.139326389 - Chemical Formula
- C18H21ClN2
- Synonyms
- Chlorcyclizin
- Chlorcyclizine
- Chlorcyclizinum
- Clorciclicina
- Clorciclizina
- Clorciclizinio
- External IDs
- Compound 47-282
Pharmacology
- Indication
Not Available
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- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AHistamine H1 receptor antagonistHumans - Absorption
Readily absorbed after oral administration and widely distributed throughout the body. Metabolised by N-demethylation to form norchlorcyclizine and by N-oxidation.
- Volume of distribution
After a single oral dose of 2 mg/kg to 4 subjects, average peak plasma concentrations of about 0.05 mg/L and 0.03 mg/L were attained in 5 h for unchanged drug and norchlorcyclizine, respectively. After oral administration of 50 mg 3 times a day for 6 days, plasma concentrations of norchlorcyclizine of 0.05 to 0.11 mg/L were reported on the first day after the cessation of treatment and plasma concentrations of 0.02 to 0.04 mg/L were found on the 10th day after cessation of treatment [Kuntzman et al. 1973].
- Protein binding
about 85 to 90%.
- Metabolism
High concentrations of the N-desmethyl metabolite are found in the liver, lungs, kidney, and spleen.
- Route of elimination
Slowly excreted in the urine; measurable amounts of norchlorcyclizine have been detected in the urine for up to 3 weeks after the cessation of chronic oral administration. About 0.5% of a single dose is excreted in the urine as the N-oxide.
- Half-life
about 12 h.
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
Pathway Category Chlorcyclizine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcrivastine The risk or severity of QTc prolongation can be increased when Chlorcyclizine is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Chlorcyclizine is combined with Adenosine. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Chlorcyclizine. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Chlorcyclizine. Alimemazine The risk or severity of QTc prolongation can be increased when Alimemazine is combined with Chlorcyclizine. Amantadine The risk or severity of QTc prolongation can be increased when Amantadine is combined with Chlorcyclizine. Amifampridine The risk or severity of QTc prolongation can be increased when Chlorcyclizine is combined with Amifampridine. Amiodarone The risk or severity of QTc prolongation can be increased when Chlorcyclizine is combined with Amiodarone. Amisulpride The risk or severity of QTc prolongation can be increased when Amisulpride is combined with Chlorcyclizine. Amitriptyline The risk or severity of QTc prolongation can be increased when Chlorcyclizine is combined with Amitriptyline. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Avoid excessive or chronic alcohol consumption. Alcohol may increase the drowsiness caused by chlorcyclizine.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Chlorcyclizine hydrochloride NPB7A7874U 14362-31-3 MSIJLVMSKDXAQN-UHFFFAOYSA-N - Active Moieties
Name Kind UNII CAS InChI Key Chloride ion ionic Q32ZN48698 16887-00-6 VEXZGXHMUGYJMC-UHFFFAOYSA-M - International/Other Brands
- Di-Paralene / Mantadil / Pruresidine / Trihistan / Zimin (New Chemical)
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ahist Tablet 25 mg/1 Oral Magna Pharmaceutcals, Inc. 2013-01-15 Not applicable US 
Bonine Kids Tablet, chewable 25 mg/1 Oral Insight Pharmaceuticals 2009-06-08 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Biclora Chlorcyclizine hydrochloride (12.5 mg/5mL) + Chlophedianol hydrochloride (12.5 mg/5mL) Liquid Oral Physicians Total Care, Inc. 2013-01-02 Not applicable US Biclora Chlorcyclizine hydrochloride (12.5 mg/5mL) + Chlophedianol hydrochloride (12.5 mg/5mL) Liquid Oral Hawthorn Pharmaceuticals, Inc. 2012-10-31 2014-10-23 US Biclora Chlorcyclizine hydrochloride (25 mg/1) + Chlophedianol hydrochloride (25 mg/1) Tablet Oral Hawthorn Pharmaceuticals, Inc. 2012-11-30 2014-10-23 US biclora-D Chlorcyclizine hydrochloride (12.5 mg/5mL) + Chlophedianol hydrochloride (12.5 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Liquid Oral Hawthorn Pharmaceuticals, Inc. 2012-10-08 2014-10-23 US biclora-D Chlorcyclizine hydrochloride (25 mg/1) + Chlophedianol hydrochloride (25 mg/1) + Pseudoephedrine hydrochloride (60 mg/1) Tablet Oral Hawthorn Pharmaceuticals, Inc. 2012-11-30 2014-11-30 US Dallergy Chlorcyclizine hydrochloride (25 mg/1) + Phenylephrine hydrochloride (10 mg/1) Tablet Oral Laser Pharmaceuticals, LLC 2011-11-01 2011-11-15 US Dallergy Chlorcyclizine hydrochloride (12.5 mg/1) + Phenylephrine (5 mg/1) Tablet, chewable Oral Laser Pharmaceuticals Llc 2011-11-01 2011-11-25 US Dallergy Chlorcyclizine hydrochloride (12.5 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL) Syrup Oral Laser Pharmaceuticals Llc 2011-10-18 2017-07-03 US Nasopen Chlorcyclizine hydrochloride (9.375 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Liquid Oral Gm Pharmaceuticals 2011-06-06 2015-02-28 US Nasotuss Chlorcyclizine hydrochloride (25 mg/5mL) + Codeine phosphate hemihydrate (10 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL) Liquid Oral Hawthorn Pharmaceuticals, Inc. 2010-11-08 2012-12-09 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Notuss-NX Chlorcyclizine hydrochloride (9.375 mg/5mL) + Codeine phosphate hemihydrate (10 mg/5mL) Liquid Oral Sj Pharmaceuticals, Llc 2010-11-03 2012-08-18 US Notuss-NXD Chlorcyclizine hydrochloride (9.375 mg/5mL) + Codeine phosphate hemihydrate (10 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Liquid Oral Sj Pharmaceuticals, Llc 2010-11-03 2012-08-18 US
Categories
- ATC Codes
- R06AE04 — Chlorcyclizine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- N-methylpiperazines / Chlorobenzenes / Aralkylamines / Aryl chlorides / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- 1,4-diazinane / Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Chlorobenzene / Diphenylmethane / Halobenzene
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- M26C4IP44P
- CAS number
- 82-93-9
- InChI Key
- 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
- IUPAC Name
- 1-[(4-chlorophenyl)(phenyl)methyl]-4-methylpiperazine
- SMILES
- CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1
References
- Synthesis Reference
Baltzly, R. and Castillo, J.C.; U.S. Patent 2,630,435; March 3, 1953; assigned to Burroughs- Wellcome & Co. (USA.) Inc.
- General References
- Enright BP, Gu YZ, Snyder RD, Dugyala RR, Obert LA, Treinen KA, McIntyre BS, Veneziale RW: Effects of the histamine H1 antagonist chlorcyclizine on rat fetal palate development. Birth Defects Res B Dev Reprod Toxicol. 2010 Dec;89(6):474-84. doi: 10.1002/bdrb.20261. [Article]
- KUNTZMAN R, KLUTCH A, TSAI I, BURNS JJ: PHYSIOLOGICAL DISTRIBUTION AND METABOLIC INACTIVATION OF CHLORCYCLIZINE AND CYCLIZINE. J Pharmacol Exp Ther. 1965 Jul;149:29-35. [Article]
- External Links
- Human Metabolome Database
- HMDB0240224
- PubChem Compound
- 2710
- PubChem Substance
- 175427165
- ChemSpider
- 2609
- BindingDB
- 50329371
- 2354
- ChEBI
- 94402
- ChEMBL
- CHEMBL22150
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Chlorcyclizine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Withdrawn Treatment Seasonal Allergic Rhinitis 1 1, 2 Completed Treatment Chronic Hepatitis C Virus (HCV) Infection 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 25 mg/1 Tablet Oral Tablet, chewable Oral 25 mg/1 Syrup Oral Tablet, chewable Oral Liquid Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 216 Baltzly, R. and Castillo, J.C.; U.S. Patent 2,630,435; March 3, 1953; assigned to Burroughs- Wellcome & Co. (USA.) Inc. - Predicted Properties
Property Value Source Water Solubility 0.0424 mg/mL ALOGPS logP 4.16 ALOGPS logP 4.15 Chemaxon logS -3.8 ALOGPS pKa (Strongest Basic) 7.63 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 6.48 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 89.74 m3·mol-1 Chemaxon Polarizability 33.89 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Download (22.7 KB)
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Enright BP, Gu YZ, Snyder RD, Dugyala RR, Obert LA, Treinen KA, McIntyre BS, Veneziale RW: Effects of the histamine H1 antagonist chlorcyclizine on rat fetal palate development. Birth Defects Res B Dev Reprod Toxicol. 2010 Dec;89(6):474-84. doi: 10.1002/bdrb.20261. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Regulator
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Martinez-Gomez MA, Carril-Aviles MM, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ: Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. J Chromatogr A. 2007 Apr 20;1147(2):261-9. doi: 10.1016/j.chroma.2007.02.054. Epub 2007 Feb 22. [Article]
Drug created at January 28, 2014 20:53 / Updated at December 02, 2023 07:00