Meclizine

Meclizine
Clinical data
Trade names	Bonine, Antivert, others
Other names	Meclozine
AHFS/Drugs.com	Monograph
MedlinePlus	a682548
License data	US DailyMed: Meclizine;
Routes of; administration	By mouth, under the tongue, in the cheek
ATC code	R06AE05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: OTC; US: OTC;
Pharmacokinetic data
Bioavailability	22 - 32%
Metabolism	Liver (CYP2D6)
Elimination half-life	5-6 hours
Identifiers
	IUPAC name (RS)-1-[(4-chlorophenyl)(phenyl)methyl]-4-(3-methylbenzyl)piperazine;
CAS Number	569-65-3 ;
PubChem CID	4034;
IUPHAR/BPS	2757;
DrugBank	DB00737 ;
ChemSpider	3894 ;
UNII	3L5TQ84570;
KEGG	D08163; D01317;
ChEMBL	ChEMBL1623 ;
CompTox Dashboard (EPA)	DTXSID0023242 ;
ECHA InfoCard	100.008.477
Chemical and physical data
Formula	C25H27ClN2
Molar mass	390.96 g·mol−1
3D model (JSmol)	Interactive image;
Boiling point	230 °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 ;
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Meclizine, sold under the brand name Bonine, among others, is an antihistamine used to treat motion sickness and dizziness (vertigo).^[3] It is taken by mouth.^[3] Effects generally begin in an hour and last for up to a day.^[3]

Common side effects include sleepiness and dry mouth.^[3] Serious side effects may include allergic reactions.^[3] Use in pregnancy appears safe, but has not been well studied; use in breastfeeding is of unclear safety.^[4] It is believed to work in part by anticholinergic and antihistamine mechanisms.^[3]

Meclizine was patented in 1951 and came into medical use in 1953.^[5] It is available as a generic medication and often over the counter.^[3]^[6] In 2021, it was the 136th most commonly prescribed medication in the United States, with more than 4 million prescriptions.^[7]^[8]

^ Sun J, Liu J, Zhang J, Xia H (June 2021). "Meclizine-loaded nanostructured lipid carriers to manage nausea and vomiting: Oral bioavailability improvement". Journal of Drug Delivery Science and Technology. 63: 102432. doi:10.1016/j.jddst.2021.102432.
^ Wang Z, Lee B, Pearce D, Qian S, Wang Y, Zhang Q, et al. (September 2012). "Meclizine metabolism and pharmacokinetics: formulation on its absorption". Journal of Clinical Pharmacology. 52 (9): 1343–1349. doi:10.1177/0091270011414575. PMID 21903894.
^ ^a ^b ^c ^d ^e ^f ^g "Meclizine Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 22 March 2019.
^ "Meclizine Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 547. ISBN 9783527607495.
^ Cappa M, Cianfarani S, Ghizzoni L, Loche S, Maghnie M (2015). Advanced Therapies in Pediatric Endocrinology and Diabetology: Workshop, Rome, October 2014. Karger Medical and Scientific Publishers. p. 101. ISBN 9783318056372.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Meclizine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

[bioavail-1] Sun J, Liu J, Zhang J, Xia H (June 2021). "Meclizine-loaded nanostructured lipid carriers to manage nausea and vomiting: Oral bioavailability improvement". Journal of Drug Delivery Science and Technology. 63: 102432. doi:10.1016/j.jddst.2021.102432.

[pharmacokinetics-2] Wang Z, Lee B, Pearce D, Qian S, Wang Y, Zhang Q, et al. (September 2012). "Meclizine metabolism and pharmacokinetics: formulation on its absorption". Journal of Clinical Pharmacology. 52 (9): 1343–1349. doi:10.1177/0091270011414575. PMID 21903894.

[AHFS2019-3] ^ ^a ^b ^c ^d ^e ^f ^g "Meclizine Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 22 March 2019.

[Preg2019-4] "Meclizine Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.

[Fis2006-5] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 547. ISBN 9783527607495.

[6] Cappa M, Cianfarani S, Ghizzoni L, Loche S, Maghnie M (2015). Advanced Therapies in Pediatric Endocrinology and Diabetology: Workshop, Rome, October 2014. Karger Medical and Scientific Publishers. p. 101. ISBN 9783318056372.

[7] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[8] "Meclizine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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