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
Synonyms
  • Meclizine
  • Meclozine
  • Nevidoxine
Product Ingredients
IngredientUNIICASInChI Key
Meclizine HydrochlorideHDP7W44CIO31884-77-2BAAVORPTHSKWGJ-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AntivertTablet12.5 mg/1OralRoerig1997-04-11Not applicableUs
AntivertTablet50 mg/1OralRoerig1997-04-11Not applicableUs
AntivertTablet25 mg/1OralPhysicians Total Care, Inc.1997-04-112012-06-30Us
AntivertTablet25 mg/1OralRoerig1997-04-11Not applicableUs
Meclizine HydrochlorideTablet25 mg/1OralWatson Pharmaceuticals2006-03-28Not applicableUs
Meclizine HydrochlorideTablet12.5 mg/1OralWatson Pharmaceuticals2006-03-28Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MeclizineTablet12.5 mg/1OralDirectrx2016-04-28Not applicableUs
Meclizine HydrochlorideTablet25 mg/1OralMas Management Group, Inc.2012-04-30Not applicableUs
Meclizine HydrochlorideTablet12.5 mg/1OralJubilant Cadista Pharmaceuticals Inc.2010-06-04Not applicableUs
Meclizine HydrochlorideTablet25 mg/1OralAv Kare, Inc.2012-05-11Not applicableUs
Meclizine HydrochlorideTablet12.5 mg/1OralAvPAK2013-08-08Not applicableUs
Meclizine HydrochlorideTablet12.5 mg/1OralPhysicians Total Care, Inc.1994-07-05Not applicableUs54868 008920180907 15195 1vn5xxc
Meclizine HydrochlorideTablet25 mg/1OralRemedy Repack2014-11-112017-01-20Us
Meclizine HydrochlorideTablet25 mg/1OralNorthwind Pharmaceuticals2014-07-24Not applicableUs
Meclizine HydrochlorideTablet12.5 mg/1OralNucare Pharmaceuticals, Inc.2012-04-30Not applicableUs
Meclizine HydrochlorideTablet25 mg/1OralREMEDYREPACK INC.2018-07-17Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BonamineTablet, multilayer, extended release25 mgOralMcneil Consumer Healthcare Division Of Johnson & Johnson IncNot applicableNot applicableCanada
Bonamine Tab 25mg ChewableTablet, chewable25 mgOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1954-12-312011-08-04Canada
BonineTablet, chewable25 mg/1OralInsight Pharmaceuticals2009-06-08Not applicableUs
BonineTablet, chewable25 mg/1OralWell Spring Pharmaceutical Corporation2017-04-18Not applicableUs
BonineTablet, chewable25 mg/1OralWell Spring Pharmaceutical Corporation2014-12-15Not applicableUs
CVS Motion Sickness Fast MeltingTablet, orally disintegrating25 mg/1OralCVS Health2015-08-27Not applicableUs
Dramamine Less DrowsyTablet25 mg/1OralMedtech Laboratories, Inc.2011-09-01Not applicableUs
Dramamine Less Drowsy FormulaTablet25 mg/1OralMc Neil Consumer Healthcare Div. Mc Neil Ppc, Inc2008-12-012013-04-30Us
Jet-Avert Motion Sickness AidTablet25 mg/1OralBell International Laboratories2017-10-07Not applicableUs
Less Drowsy Formula Motion Sickness ReliefTablet25 mg/1OralSalado Sales, Inc.2002-06-24Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antivert TabMeclizine Hydrochloride (12.5 mg) + Niacin (50 mg)TabletOralPfizer1956-12-312000-01-24Canada
International/Other Brands
Chiclida / Meclicot / Navicalm / Postafen / Sea-Legs
Categories
UNII
3L5TQ84570
CAS number
569-65-3
Weight
Average: 390.948
Monoisotopic: 390.186276581
Chemical Formula
C25H27ClN2
InChI Key
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
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

Pharmacology

Indication

For the prevention and treatment of nausea, vomiting, or dizziness associated with motion sickness.

Associated Conditions
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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
UNuclear receptor subfamily 1 group I member 3
inverse agonist
Human
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
PathwayCategory
Meclizine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Meclizine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Meclizine.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative and stimulatory activities of Meclizine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Meclizine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Meclizine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Meclizine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Meclizine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Meclizine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AcepromazineThe risk or severity of adverse effects can be increased when Meclizine is combined with Acepromazine.
AceprometazineThe risk or severity of adverse effects can be increased when Meclizine is combined with Aceprometazine.
Food Interactions
  • Take with food to reduce irritation. Avoid alcohol.

References

Synthesis Reference

U.S. Patent 2,709,169.

General References
Not Available
External Links
Human Metabolome Database
HMDB0014875
KEGG Compound
C07116
PubChem Compound
4034
PubChem Substance
46507782
ChemSpider
3894
BindingDB
81467
ChEBI
6709
ChEMBL
CHEMBL1623
Therapeutic Targets Database
DAP000795
PharmGKB
PA450338
IUPHAR
2757
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Meclizine
ATC Codes
R06AE55 — Meclozine, combinationsR06AE05 — Meclozine
AHFS Codes
  • 56:22.08 — Antihistamines

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
1RecruitingTreatmentHepatocellular,Carcinoma1
2CompletedTreatmentCessation, Smoking1
3RecruitingTreatmentVertigo, Peripheral1
4RecruitingOtherDrug Reaction1
Not AvailableCompletedPreventionPost-Operative Nausea and Vomiting (PONV)1
Not AvailableCompletedTreatmentBenign Paroxysmal Positional Vertigo (BPPV)1

Pharmacoeconomics

Manufacturers
  • Pfizer inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • AJ Bart
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Blenheim Pharmacal
  • Bryant Ranch Prepack
  • Cadista Pharmaceuticals Inc.
  • Cardinal Health
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Group Health Cooperative
  • H and H Laboratories
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Kaiser Foundation Hospital
  • Kraft Pharmaceutical Co. Inc.
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Med Tek Pharmaceuticals Inc.
  • Medique Products
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nexgen Pharma Inc.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Patheon Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacia Inc.
  • Pharmedix
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Sandoz
  • Stat Rx Usa
  • Stat Scripts LLC
  • Sunmark
  • Tya Pharmaceuticals
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Veratex Corp.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral50 mg/1
TabletOral
Tablet, multilayer, extended releaseOral25 mg
Tablet, chewableOral25 mg
Tablet, orally disintegratingOral25 mg/1
TabletOral12.5 mg/1
TabletOral25 mg/1
Tablet, film coatedOral25 mg/1
Tablet, chewableOral25 mg/251
Tablet, film coatedOral12.5 mg/1
Tablet, chewableOral25 mg/1
Film, solubleOral25 mg/1
Prices
Unit descriptionCostUnit
Meclizine HCl 100 25 mg tablet Box89.97USD box
Antivert 50 mg tablet2.12USD tablet
Antivert 25 mg tablet1.23USD tablet
Meclizine hcl powder1.04USD g
Vertin-32 tablet0.9USD tablet
Antivert 12.5 mg tablet0.82USD tablet
Meclizine HCl 25 mg tablet0.67USD tablet
Meclizine 12.5 mg tablet0.62USD tablet
Sm motion sicknes 25 mg tablet0.5USD tablet
Meclizine HCl 12.5 mg tablet0.43USD tablet
Dramamine less drowsy tablet0.42USD tablet
Bonamine 25 mg Chewable Tablet0.33USD tablet
Dramamine 50 mg tablet0.28USD tablet
Meclizine 25 mg tablet0.07USD tablet
Medi-meclizine 25 mg tablet0.06USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)217-224U.S. Patent 2,709,169.
water solubility0.1gm/100mlNot Available
logP5.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00103 mg/mLALOGPS
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
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9318
Blood Brain Barrier+0.9656
Caco-2 permeable+0.6369
P-glycoprotein substrateSubstrate0.7422
P-glycoprotein inhibitor IInhibitor0.8149
P-glycoprotein inhibitor IINon-inhibitor0.8042
Renal organic cation transporterInhibitor0.7859
CYP450 2C9 substrateNon-substrate0.8416
CYP450 2D6 substrateNon-substrate0.5134
CYP450 3A4 substrateNon-substrate0.6059
CYP450 1A2 substrateInhibitor0.806
CYP450 2C9 inhibitorNon-inhibitor0.9698
CYP450 2D6 inhibitorInhibitor0.9521
CYP450 2C19 inhibitorInhibitor0.5209
CYP450 3A4 inhibitorNon-inhibitor0.8896
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7063
Ames testNon AMES toxic0.8536
CarcinogenicityNon-carcinogens0.9343
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3803 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6113
hERG inhibition (predictor II)Inhibitor0.8104
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-052r-1920000000-da1d25573308648315fa
Mass Spectrum (Electron Ionization)MSsplash10-0ap0-1910000000-a39cf62803f22b3df281
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0090000000-66c42b235873c2a66976
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0090000000-02a85fbc5761853f587f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0uxr-0590000000-4633d1c1f89a98d9a694
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0gb9-0940000000-38b1d47fb87eb43db9bd
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0910000000-0787c462628db9403567
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-9b3d5063cf1e4fd0ecda
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0390000000-10b11855a2539537e5af

Taxonomy

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
Phenylmethylamines / Benzylamines / Toluenes / N-alkylpiperazines / Chlorobenzenes / Aralkylamines / Aryl chlorides / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents
Diphenylmethane / Benzylamine / Phenylmethylamine / Chlorobenzene / Halobenzene / Aralkylamine / N-alkylpiperazine / Toluene / Aryl chloride / Aryl halide
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
diarylmethane (CHEBI:6709)

Targets

Kind
Protein
Organism
Human
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
  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:7513381]
  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:1350745]
  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:1362160]
  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:1678430]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inverse agonist
General Function
Zinc ion binding
Specific Function
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
Gene Name
NR1I3
Uniprot ID
Q14994
Uniprot Name
Nuclear receptor subfamily 1 group I member 3
Molecular Weight
39942.145 Da
References
  1. Huang W, Zhang J, Wei P, Schrader WT, Moore DD: Meclizine is an agonist ligand for mouse constitutive androstane receptor (CAR) and an inverse agonist for human CAR. Mol Endocrinol. 2004 Oct;18(10):2402-8. Epub 2004 Jul 22. [PubMed:15272053]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:30