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Identification
NameMeclizine
Accession NumberDB00737  (APRD00354)
TypeSmall Molecule
GroupsApproved
Description

A histamine H1 antagonist used in the treatment of motion sickness, vertigo, and nausea during pregnancy and radiation sickness. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
MeclizineNot AvailableNot Available
MeclozineNot AvailableINN
NevidoxineNot AvailableNot Available
Salts
Name/CAS Structure Properties
Meclizine Hydrochloride
Thumb
  • InChI Key: BAAVORPTHSKWGJ-UHFFFAOYNA-N
  • Monoisotopic Mass: 444.173519006
  • Average Mass: 445.424
DBSALT000678
Brand names
NameCompany
AntivertNot Available
BonamineNot Available
BonineNot Available
ChiclidaNot Available
DramamineNot Available
MeclicotNot Available
NavicalmNot Available
PostafenNot Available
Sea-LegsNot Available
Brand mixtures
Brand NameIngredients
Antivert TabMeclizine Hydrochloride + Nicotinic Acid
EmesafeneMeclizine Hydrochloride + pyridoxine
Categories
CAS number569-65-3
WeightAverage: 390.948
Monoisotopic: 390.186276581
Chemical FormulaC25H27ClN2
InChI KeyOCJYIGYOJCODJL-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
IUPAC Name
1-[(4-chlorophenyl)(phenyl)methyl]-4-[(3-methylphenyl)methyl]piperazine
SMILES
CC1=CC(CN2CCN(CC2)C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassDiphenylmethanes
Direct parentDiphenylmethanes
Alternative parentsToluenes; Chlorobenzenes; Piperazines; Aryl Chlorides; Diazinanes; Tertiary Amines; Polyamines; Organochlorides
Substituentstoluene; chlorobenzene; aryl halide; piperazine; 1,4-diazinane; aryl chloride; tertiary amine; polyamine; organohalogen; organochloride; organonitrogen compound; amine
Classification descriptionThis compound belongs to the diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Pharmacology
IndicationFor the prevention and treatment of nausea, vomiting, or dizziness associated with motion sickness.
PharmacodynamicsMeclizine, 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 actionAlong 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.
AbsorptionWell absorbed
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half life6 hours
ClearanceNot Available
ToxicitySymptoms of overdose include drowsiness and anticholinergic effects. LD50=mg/kg (orally in rat).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9318
Blood Brain Barrier + 0.9656
Caco-2 permeable + 0.6369
P-glycoprotein substrate Substrate 0.7422
P-glycoprotein inhibitor I Inhibitor 0.8149
P-glycoprotein inhibitor II Non-inhibitor 0.8042
Renal organic cation transporter Inhibitor 0.7859
CYP450 2C9 substrate Non-substrate 0.8416
CYP450 2D6 substrate Non-substrate 0.5134
CYP450 3A4 substrate Non-substrate 0.6059
CYP450 1A2 substrate Inhibitor 0.806
CYP450 2C9 substrate Non-inhibitor 0.9698
CYP450 2D6 substrate Inhibitor 0.9521
CYP450 2C19 substrate Inhibitor 0.5209
CYP450 3A4 substrate Non-inhibitor 0.8896
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7063
Ames test Non AMES toxic 0.8536
Carcinogenicity Non-carcinogens 0.9343
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.3803 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Strong inhibitor 0.6113
hERG inhibition (predictor II) Inhibitor 0.8104
Pharmacoeconomics
Manufacturers
  • Pfizer inc
Packagers
Dosage forms
FormRouteStrength
Tablet, chewableOral
Prices
Unit descriptionCostUnit
Meclizine HCl 100 25 mg tablet Box89.97USDbox
Antivert 50 mg tablet2.12USDtablet
Antivert 25 mg tablet1.23USDtablet
Meclizine hcl powder1.04USDg
Vertin-32 tablet0.9USDtablet
Antivert 12.5 mg tablet0.82USDtablet
Meclizine HCl 25 mg tablet0.67USDtablet
Meclizine 12.5 mg tablet0.62USDtablet
Sm motion sicknes 25 mg tablet0.5USDtablet
Meclizine HCl 12.5 mg tablet0.43USDtablet
Dramamine less drowsy tablet0.42USDtablet
Bonamine 25 mg Chewable Tablet0.33USDtablet
Dramamine 50 mg tablet0.28USDtablet
Meclizine 25 mg tablet0.07USDtablet
Medi-meclizine 25 mg tablet0.06USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point217-224U.S. Patent 2,709,169.
water solubility0.1gm/100mlNot Available
logP5.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00103ALOGPS
logP5.59ALOGPS
logP6.39ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.39 m3·mol-1ChemAxon
Polarizability44.87 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

U.S. Patent 2,709,169.

General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC07116
PubChem Compound4034
PubChem Substance46507782
ChemSpider3894
Therapeutic Targets DatabaseDAP000795
PharmGKBPA450338
IUPHAR2757
Guide to Pharmacology2757
Drug Product Database220442
RxListhttp://www.rxlist.com/cgi/generic/mecliz.htm
Drugs.comhttp://www.drugs.com/meclizine.html
WikipediaMeclizine
ATC CodesR06AE05
AHFS Codes
  • 56:22.08
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
RivastigminePossible antagonism of action
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Meclizine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
TrimethobenzamideTrimethobenzamide and Meclizine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine and Meclizine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
TrospiumTrospium and Meclizine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions
  • Take with food to reduce irritation. Avoid alcohol.

Targets

1. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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

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Drug created on June 13, 2005 07:24 / Updated on May 23, 2014 15:54