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Meclizine

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This is an old revision of this page, as edited by Beetstra (talk | contribs) at 19:11, 14 December 2010 (Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 19:11, 14 December 2010 by Beetstra (talk | contribs) (Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Meclizine
Clinical data
Routes of
administration
Oral, Sublingual/Buccal
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolismhepatic
Elimination half-life6 hours
Identifiers
IUPAC name
  • (R/S)-1--4-(3-methylbenzyl)piperazine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.008.477 Edit this at Wikidata
Chemical and physical data
FormulaC25H27ClN2
Molar mass390.948 g/mol g·mol
3D model (JSmol)
Boiling point230 °C (446 °F)
SMILES
  • Clc1ccc(cc1)C(c2ccccc2)N3CCN(CC3)Cc4cccc(c4)C
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
  • Key:OCJYIGYOJCODJL-UHFFFAOYSA-N
  (verify)

Meclizine is an antihistamine considered to be an antiemetic. It is sold under the brand names of Bonine, Bonamine, Antivert, Postafen, Sea Legs, and Dramamine (Less Drowsy Formulation). Emesafene is a combination of meclizine (1/3) and pyridoxine (2/3). In Canada, Antivert Tab (which is no longer available) was a combination of meclizine and nicotinic acid.


Classification

Meclizine is a first-generation antihistamine of the piperazine class. Meclizine is structurally and pharmacologically similar to buclizine, cyclizine, and hydroxyzine. It is used as an antivertigo/antiemetic agent, specifically, in the prevention and treatment of nausea, vomiting, and dizziness associated with motion sickness.

Mechanism of Action

Meclizine is an antagonist at H1-receptors. It possesses anticholinergic, central nervous system depressant, and local anesthetic effects. Its antiemetic and antivertigo effects are not fully understood, but its central anticholinergic properties are partially responsible. The drug depresses labyrinth excitability and vestibular stimulation, and it may affect the medullary chemoreceptor trigger zone.

Uses

Meclizine is FDA approved to treat symptoms of motion sickness and for management of vertigo that stems from diseases affecting the vestibular system. Meclizine's safety and efficacy in children younger than 12 years old has not been established, therefore use in this population is not recommended. Also, meclizine should be taken with caution in the elderly (greater than 65 years old) because of increased risk of confusion and amnesia.

Motion sickness

Meclizine is effective in inhibiting the symptoms of motion sickness, such as nausea, vomiting, and dizziness. The recommended dose is 25-50 mg orally, taken 1 hour before travel. The dose may be repeated every 24 hours as needed.

Vertigo

Meclizine may be effective in relieving vertigo experienced as a result of inner ear infections or other conditions. The recommended dose is 25-100 mg per day orally, separated into divided doses.

Side Effects

Some common side effects such as drowsiness, dry mouth, and tiredness may occur. Meclizine has been shown to have less dry mouth side effects than the traditional treatment for motion sickness, transdermal scopolamine. A very serious allergic reaction to this drug is unlikely, but seek immediate medical attention if it occurs. Symptoms of a serious allergic reaction may include: rash, itching/swelling, severe dizziness, and/or trouble breathing.

Drowsiness

Drowsiness may result as a side effect of taking meclizine. Users are advised not to operate heavy machinery while under the influence. The consumption of alcohol while under the influence of meclizine may result in additional drowsiness.

Special Considerations in the Elderly

As with any anticholinergic agent, meclizine may cause confusion or aggravate symptoms in those with dementia in the geriatric population (those greater than 65 years of age). Therefore caution should be used when administering meclizine to the elderly.

References

  1. DrugBank. "http://www.drugbank.ca/drugs/DB00737" David Wishard: University of Alberta, Canada. Accessed November 7, 2010.
  2. Clinical Pharmacology. "http://www.clinicalpharmacology.com", revised November 20, 2009, accessed November 7, 2010.
  3. Clinical Pharmacology. "http://www.clinicalpharmacology.com", revised November 20, 2009, accessed November 7, 2010.
  4. MICROMEDEX 2.0. "http://www.thomsonhc.com". Accessed November 7, 2010.
  5. Clinical Pharmacology. "http://www.clinicalpharmacology.com", revised November 20, 2009, accessed November 7, 2010.
  6. Clinical Pharmacology. "http://www.clinicalpharmacology.com", revised November 20, 2009, accessed November 7, 2010.
  7. Dahl E, Offer-Ohlsen D, Lillevold PE, Sandvik L. Transdermal scopolamine, oral meclizine, and placebo in motion sickness. Clinical Pharmacology And Therapeutics 1984 Jul; Vol. 36 (1), pp. 116-20. Available from: MEDLINE: Ipswich, MA. PMID 6734040
  8. MedicineNet.com: We Bring Doctors' Knowledge to You. MedicineNet Inc, San Clemente, CA. "http://www.medicinenet.com/meclizine_cyclizine-oral/article.htm". Accessed November 7, 2010.
  9. Merck Manuals, Online Medical Library: Meclizine (Drug Information Provided by Lexi-Comp). "http://www.merck.com/mmpe/print/lexicomp/meclizine.html", revised January 2010, accessed November 7, 2010.

External links

Antiemetics (A04)
5-HT3 serotonin ion
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Receptor/signaling modulators
Monoamine metabolism modulators
Monoamine reuptake inhibitors
Piperazines
Simple piperazines
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Phenylpiperazines
Benzylpiperazines
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