| 词条 | Meclizine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 402382239 | IUPAC_name = (RS)-1-[(4-chlorophenyl)(phenyl)methyl]-4-(3-methylbenzyl)piperazine | image = Meclizine.svg | width = 200px | synonyms = Meclozine | tradename = Bonamine, Antivert, others | Drugs.com = {{drugs.com|monograph|meclizine-hydrochloride}} | MedlinePlus = a682548 | pregnancy_US = B | legal_AU = S4 | legal_US = OTC | legal_CA = OTC | routes_of_administration = By mouth, under the tongue, in the cheek | bioavailability = | protein_bound = | metabolism = Liver | elimination_half-life = 6 hours | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 569-65-3 | ATC_prefix = R06 | ATC_suffix = AE05 | ATC_supplemental = | PubChem = 4034 | IUPHAR_ligand = 2757 | DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank = DB00737 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 3894 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 3L5TQ84570 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1623 | C=25 | H=27 | Cl=1 | N=2 | molecular_weight = 390.948 g/mol | smiles = Clc1ccc(cc1)C(c2ccccc2)N3CCN(CC3)Cc4cccc(c4)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = OCJYIGYOJCODJL-UHFFFAOYSA-N | boiling_point = 230 }}Meclizine, sold under the brand names Bonamine among others, is an antihistamine used to treat motion sickness and the feeling like the world is spinning.[1] It is taken by mouth.[1] Effects generally begin in an hour and last for up to a day.[1] Common side effects include sleepiness and dry mouth.[1] Serious side effects may include allergic reactions.[1] Use in pregnancy appears safe but has not been well studied while use in breastfeeding is of unclear safety.[2] It is believed to work in part by anticholinergic and antihistamine mechanisms.[1] Meclizine was patented in 1951 and came into medical use in 1953.[3] It is avaliable as a generic medication and often over the counter.[1][4] In the United States the wholesale cost per dose is about 0.03 USD.[5] It is not avaliable in Australia.[6] In 2016 it was the 162nd most prescribed medication in the United States with more than three million prescriptions.[7] Medical usesMeclizine is used to treat symptoms of motion sickness. Safety and efficacy in children younger than twelve years of age has not been established; therefore, use in this population is not recommended.{{citation needed|date=March 2019}} Meclizine should be taken with caution in the elderly due to increased risk of confusion and amnesia.[8] Motion sicknessMeclizine is effective in inhibiting the symptoms of motion sickness, such as nausea, vomiting, and dizziness.[9] The drug is safe for treating nausea in pregnancy[10] and is a first-line therapy for this use.[11][12] Doxylamine is similarly safe. Meclizine may not be strong enough for especially sickening motion stimuli and second-line defenses should be tried in those cases.[13] VertigoMeclizine is effective in relieving vertigo experienced as a result of inner ear infection or positional or chronic vertigo.[14] Side effectsSome common side effects such as drowsiness, dry mouth, and tiredness may occur. Meclizine has been shown to have fewer dry mouth side effects than the traditional treatment for motion sickness, transdermal scopolamine.[15] A very serious allergic reaction to this drug is unlikely, but immediate medical attention should be sought if it occurs. Symptoms of a serious allergic reaction may include rash, itching, swelling, severe dizziness, and trouble breathing.[16] DrowsinessDrowsiness 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. ElderlyAs with any anticholinergic agent, meclizine may cause confusion or aggravate symptoms in those with dementia in the geriatric population (older than 65 years). Therefore, caution should be used when administering meclizine to the elderly.[17] Mechanism of actionMeclizine 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.[24] Meclizine also is a dopamine antagonist at D1-like and D2-like receptors{{citation needed|date=September 2015}} but does not cause catalepsy{{refn|group=note|"[C]atalepsy was assessed by the bar method[:] the front paws were gently placed on a horizontal metal bar with 2 mm diameter suspended 4 cm above, and the length of time the mouse maintains this abnormal posture was measured."[18]}} in mice, perhaps because of its anticholinergic activity.[18] ChemistryMeclizine is a first-generation antihistamine (nonselective H1 antagonist) of the piperazine class. It is structurally and pharmacologically similar to buclizine, cyclizine, and hydroxyzine, but has a shorter half-life of six hours compared to cyclizine and hydroxyzine with about 20 hours (though half-life should not be confused with duration). It is used as an antivertigo/antiemetic agent, specifically in the prevention and treatment of nausea, vomiting, and dizziness associated with motion sickness.[19] Meclizine is sometimes combined with opioids, especially ones of the open-chain class like methadone, dextropropoxyphene, and dipipanone. Similarly, Diconal is a combination drug containing dipipanone and cyclizine.{{citation needed|date=March 2019}} Synthesis(4-Chlorphenyl)-phenylmethanol is halogenated with thionyl chloride before adding acetylpiperazine. The acetyl group is cleaved with diluted sulfuric acid. An N-alkylation of the piperazine ring with 3-methylbenzylchloride completes the synthesis.[20] Alternatively, the last step can be replaced by a reductive N-alkylation with 3-methylbenzaldehyde. The reductive agent is hydrogen, and Raney nickel is used as a catalyst.[21][22] Meclizine is obtained and used as a racemate, a 1:1 mixture of the two stereoisomers. Drug forms contain the racemic dihydrochloride. NamesMeclizine is an international nonproprietary name.[23] It is sold under the brand names Bonine, Bonamine, Antivert, Postafen, Sea Legs, and Dramamine II (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.[24] Notes1. ^1 2 3 4 5 6 {{cite web |title=Meclizine Hydrochloride Monograph for Professionals |url=https://www.drugs.com/monograph/meclizine-hydrochloride.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |accessdate=22 March 2019 |language=en}} 2. ^{{cite web |title=Meclizine Use During Pregnancy |url=https://www.drugs.com/pregnancy/meclizine.html |website=Drugs.com |accessdate=3 March 2019 |language=en}} 3. ^{{cite book |last1=Fischer |first1=Jnos |last2=Ganellin |first2=C. Robin |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=547 |url=https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA547 |language=en}} 4. ^{{cite book |last1=Cappa |first1=M. |last2=Cianfarani |first2=S. |last3=Ghizzoni |first3=L. |last4=Loche |first4=S. |last5=Maghnie |first5=M. |title=Advanced Therapies in Pediatric Endocrinology and Diabetology: Workshop, Rome, October 2014 |date=2015 |publisher=Karger Medical and Scientific Publishers |isbn=9783318056372 |page=101 |url=https://books.google.ca/books?id=myNRCwAAQBAJ&pg=PA101 |language=en}} 5. ^{{cite web |title=NADAC as of 2019-02-27 |url=https://data.medicaid.gov/Drug-Pricing-and-Payment/NADAC-as-of-2019-02-27/s7c9-pfa6 |website=Centers for Medicare and Medicaid Services |accessdate=3 March 2019 |language=en}} 6. ^{{cite book |last1=McKenzie |first1=Gayle |last2=Broyles |first2=Bonita |last3=Evans |first3=Mary E. |last4=Page |first4=Rachel |last5=Pleunik |first5=Sussan |last6=Reiss |first6=Barry S. |title=Pharmacology in Nursing: Australian and New Zealand Edition with Student Resource Access 12 Months |date=2016 |publisher=Cengage AU |isbn=9780170362030 |page=569 |url=https://books.google.ca/books?id=fkVMDwAAQBAJ&pg=PA569 |language=en}} 7. ^{{cite web |title=The Top 300 of 2019 |url=https://clincalc.com/DrugStats/Top300Drugs.aspx |website=clincalc.com |accessdate=22 December 2018}} 8. ^MICROMEDEX 2.0. Accessed November 7, 2010.{{Full citation needed|date=August 2010}} 9. ^{{Cite web|url=https://www.webmd.com/drugs/2/drug-144800/motion-sickness-meclizine-oral/details|title=Drugs & Medications|website=www.webmd.com|language=en|access-date=2018-12-28}} 10. ^{{cite journal |vauthors=Källén B, Mottet I |title=Delivery outcome after the use of meclizine in early pregnancy |journal=European Journal of Epidemiology |volume=18 |issue=7 |pages=665–669 |year=2003 |pmid=12952140 |url=http://www.kluweronline.com/art.pdf?issn=0393-2990&volume=18&page=665 |accessdate=2010-09-17 |doi=10.1023/a:1024891618953}} 11. ^{{cite journal|url=http://www.arznei-telegramm.de/html/2009_10/0910087_01.html|journal=Arznei-Telegramm|title=Antiemetische Therapie bei Schwangerschaftserbrechen|trans-title=Antiemetic therapy in pregnancy|year=2009|volume=40|pages=87–89|language=German}} 12. ^Embryotox: Meclozin {{de icon}} 13. ^{{Cite web |url=http://oai.dtic.mil/oai/oai?verb=getRecord&metadataPrefix=html&identifier=ADA511823 |authors=Lawson, B. D., McGee, H. A., Castaneda, M. A., Golding, J. F., Kass, S. J., & McGrath, C. M. |year=2009 |title=Evaluation of Several Common Antimotion Sickness Medications and Recommendations Concerning Their Potential Usefulness During Special Operations |accessdate=2016-04-18}} 14. ^{{cite journal |last1=Cohen |first1=Bernard |title=Meclizine and Placebo in Treating Vertigo of Vestibular Origin |journal=Archives of Neurology |date=1 August 1972 |volume=27 |issue=2 |pages=129 |doi=10.1001/archneur.1972.00490140033006 }} 15. ^Dahl E, Offer-Ohlsen D, Lillevold PE, Sandvik L. Transdermal scopolamine, oral meclizine, and placebo in motion sickness. Clinical Pharmacology And Therapeutics [Clin Pharmacol Ther] 1984 Jul; Vol. 36 (1), pp. 116-20. Available from: MEDLINE: Ipswich, MA. {{PMID|6734040}} 16. ^Meclizine - oral, Antivert, D-vert, Dramamine II. Accessed November 7, 2010. 17. ^Merck Manuals, Online Medical Library: Meclizine (Drug Information Provided by Lexi-Comp), revised January 2010, accessed November 7, 2010. 18. ^1 {{cite journal |vauthors=Haraguchi K, Ito K, Kotaki H, Sawada Y, Iga T |title=Prediction of drug-induced catalepsy based on dopamine D1, D2, and muscarinic acetylcholine receptor occupancies |journal=Drug Metabolism and Disposition |volume=25 |issue=6 |pages=675–684 |year=1997 |pmid=9193868 |url=http://dmd.aspetjournals.org/cgi/pmidlookup?view=long&pmid=9193868 |accessdate=2014-06-12 }} 19. ^1 Clinical Pharmacology. Clinical Pharmacology, revised November 20, 2009, accessed November 7, 2010.{{Full citation needed|date=August 2010}} 20. ^{{cite book|authors=J.-H. Fuhrkop, G. Li|title=Organic Synthesis. Concepts and Methods|publisher=Wiley|year=2003|page=237|isbn=978-3-527-30272-7}} 21. ^US 2 709 169 (UCB, 1955) 22. ^{{cite book|authors=A. Kleemann, J. Engel, B. Kutscher, D. Reichert|title=Pharmaceutical Substances. Synthesis, Patents, Applications|edition=4|publisher=Thieme|year=2001|isbn=3-13-115134-X}} 23. ^Guidelines on the Use of INNs for Pharmaceutical Substances (1997). Accessed November, 2013 "Guidance on INN." WHO. 24. ^DrugBank. Drugbank: Drug card for Meclizine David Wishard: University of Alberta, Canada. Accessed November 7, 2010. References{{reflist}}External links
| title = Medical uses | titlestyle = background:#ccccff | list1 ={{Antiemetics}}{{Antihistamines}}{{Motion sickness}}{{Hallucinogens}} }}{{Navboxes | title = Pharmacodynamics | titlestyle = background:#ccccff | list1 ={{Histamine receptor modulators}}{{Ion channel modulators}}{{Muscarinic acetylcholine receptor modulators}}{{Xenobiotic-sensing receptor modulators}} }} 6 : Antiemetics|Chloroarenes|Piperazines|Motion sickness|Pregnane X receptor agonists|RTT |
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