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Identification
Name Meclizine
Accession Number DB00737 (APRD00354)
Type small molecule
Groups approved
Description

A histamine H1 antagonist used in the treatment of motion sickness, vertigo, and nausea during pregnancy and radiation sickness. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Ancolan
  • Ancolon
  • Antivert
  • Antivert/25
  • Antivert/50
  • Bonadettes
  • Bonadoxin
  • Bonamine
  • Bonine
  • Calmonal
  • Chiclida
  • Diadril
  • Dramamine
  • Dramamine II
  • Histamethine
  • Histamethizine
  • Histametizine
  • Histametizyne
  • Itinerol
  • Marex
  • Meclicot
  • Meclizine Hcl
  • Meclozine
  • Medivert
  • Monamine
  • Navicalm
  • Neo-Istafene
  • Neo-Suprimal
  • Neo-Suprimel
  • Parachloramine
  • Peremesin
  • Postafene
  • Ravelon
  • Sabari
  • Sea-Legs
  • Siguran
  • Subari
  • Suprimal
  • Travelon
  • Veritab
  • Vomisseis
  • Vomissels
Brand name mixtures
  • Antivert Tab (Meclizine Hydrochloride + Nicotinic Acid)
Categories
  • Antiemetics
  • Anti-Allergic Agents
  • Histamine H1 Antagonists
  • Antihistamines
CAS number 569-65-3
Weight Average: 390.948
Monoisotopic: 390.186276581
Chemical Formula C25H27ClN2
InChI Key InChIKey=OCJYIGYOJCODJL-UHFFFAOYSA-N
InChI
InChI=1S/C25H27ClN2/c1-20-6-5-7-21(18-20)19-27-14-16-28(17-15-27)25(22-8-3-2-4-9-22)23-10-12-24(26)13-11-23/h2-13,18,25H,14-17,19H2,1H3
Plain Text
IUPAC Name
1-[(4-chlorophenyl)(phenyl)methyl]-4-[(3-methylphenyl)methyl]piperazine
SMILES
CC1=CC=CC(CN2CCN(CC2)C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Diphenylmethanes
Substructures
  • Piperazines
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Aliphatic and Aryl Amines
  • Diphenylmethanes
  • Heterocyclic compounds
  • Aromatic compounds
Pharmacology
Indication For the prevention and treatment of nausea, vomiting, or dizziness associated with motion sickness.
Pharmacodynamics Meclizine, a piperazine-derivative H1-receptor antagonist similar to buclizine, cyclizine, and hydroxyzine, is used as an antivertigo/antiemetic agent. Meclizine is used in the management of nausea, vomiting, and dizziness associated with motion sickness and vertigo in diseases affecting the vestibular apparatus.
Mechanism of action Along with its actions as an antagonist at H1-receptors, meclizine also possesses anticholinergic, central nervous system depressant, and local anesthetic effects. Meclizine depresses labyrinth excitability and vestibular stimulation and may affect the medullary chemoreceptor trigger zone.
Absorption Well absorbed
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Hepatic
Route of elimination Not Available
Half life 6 hours
Clearance Not Available
Toxicity Symptoms of overdose include drowsiness and anticholinergic effects. LD50=mg/kg (orally in rat).
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Pfizer inc
Packagers
Dosage forms
Form Route Strength
Tablet, chewable Oral
Prices
Unit description Cost Unit
Meclizine HCl 100 25 mg tablet Box 89.97 USD box
Antivert 50 mg tablet 2.12 USD tablet
Antivert 25 mg tablet 1.23 USD tablet
Meclizine hcl powder 1.04 USD g
Vertin-32 tablet 0.9 USD tablet
Antivert 12.5 mg tablet 0.82 USD tablet
Meclizine HCl 25 mg tablet 0.67 USD tablet
Meclizine 12.5 mg tablet 0.62 USD tablet
Sm motion sicknes 25 mg tablet 0.5 USD tablet
Meclizine HCl 12.5 mg tablet 0.43 USD tablet
Dramamine less drowsy tablet 0.42 USD tablet
Bonamine 25 mg Chewable Tablet 0.33 USD tablet
Dramamine 50 mg tablet 0.28 USD tablet
Meclizine 25 mg tablet 0.07 USD tablet
Medi-meclizine 25 mg tablet 0.06 USD tablet
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility 0.1gm/100ml PhysProp
logP 5.8 PhysProp
Predicted Properties
Property Value Source
water solubility 1.03e-03 g/l ALOGPS
logP 5.59 ALOGPS
logP 6.39 ChemAxon Molconvert
logS -5.58 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 6.48 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 119.39 ChemAxon Molconvert
polarizability 44.87 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07116 Link_out
PubChem Compound 4034 Link_out
PubChem Substance 46507782 Link_out
ChemSpider 3894 Link_out
Therapeutic Targets Database DAP000795 Link_out
PharmGKB PA450338 Link_out
Drug Product Database 220442 Link_out
RxList http://www.rxlist.com/cgi/generic/mecliz.htm Link_out
Drugs.com http://www.drugs.com/meclizine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Meclizine Link_out
ATC Codes
  • R06AE05
AHFS Codes
  • 56:22.08
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Take with food to reduce irritation. Avoid alcohol.
Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system

Organism class: human
UniProt ID: P35367 Link_out
Gene: HRH1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Oishi R, Shishido S, Yamori M, Saeki K: Comparison of the effects of eleven histamine H1-receptor antagonists on monoamine turnover in the mouse brain. Naunyn Schmiedebergs Arch Pharmacol. 1994 Feb;349(2):140-4. Pubmed
  2. Martins MA, Pasquale CP, e Silva PM, Pires AL, Ruffie C, Rihoux JP, Cordeiro RS, Vargaftig BB: Interference of cetirizine with the late eosinophil accumulation induced by either PAF or compound 48/80. Br J Pharmacol. 1992 Jan;105(1):176-80. Pubmed
  3. Pasquale CP, e Silva PM, Lima MC, Diaz BL, Rihoux JP, Vargaftig BB, Cordeiro RS, Martins MA: Suppression by cetirizine of pleurisy triggered by antigen in actively sensitized rats. Eur J Pharmacol. 1992 Nov 13;223(1):9-14. Pubmed
  4. Taniguchi K, Masuda Y, Takanaka K: Inhibitory effects of histamine H1 receptor blocking drugs on metabolic activations of neutrophils. J Pharmacobiodyn. 1991 Feb;14(2):87-93. Pubmed
Enzymes

1. Cytochrome P450 1A2

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on August 11, 2011 15:03

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.