MECLIZINE

US Approved OTC

First approved in 1954

Details

Stereochemistry	RACEMIC
Molecular Formula	C25H27ClN2
Molecular Weight	390.948
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC(CN2CCN(CC2)C(C3=CC=CC=C3)C4=CC=C(Cl)C=C4)=C1

InChI

InChIKey=OCJYIGYOJCODJL-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB00737
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/meclizine.html

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. 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. It is sold under the brand names Bonine, Bonamine, Antivert, Postafen, Sea Legs, and Dramamine II.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26239802	Inhibitor 8297
Pregnane X receptor 35 Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26239802	Agonist 2678
Ethanolamine-phosphate cytidylyltransferase 8 Target ID: Q922E4 Gene ID: 68671.0 Gene Symbol: Pcyt2 Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24142790	Inhibitor 8297	31.0 µM [Ki]
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: http://www.drugbank.ca/drugs/DB00737	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Motion sickness 43 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/010721s058lbl.pdf	Primary		Approved 8429	ANTIVERT Approved Use Effective: Management of nausea and vomiting, and dizziness associated with motion sickness. Possibly Effective: Management of vertigo associated with diseases affecting the vestibular system. Launch Date 2012
Vertigo 17 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/010721s058lbl.pdf	Primary		Approved 8429	ANTIVERT Approved Use Effective: Management of nausea and vomiting, and dizziness associated with motion sickness. Possibly Effective: Management of vertigo associated with diseases affecting the vestibular system. Launch Date 2012

C_max

Value	Dose	Co-administered	Analyte	Population
99.43 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21903894/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		MECLIZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
564.03 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21903894/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		MECLIZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21903894/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		MECLIZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
25 mg 2 times / day multiple, oral Recommended Dose: 25 mg, 2 times / day Route: oral Route: multiple Dose: 25 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32282831	unhealthy, 5-10 n = 6 Health Status: unhealthy Condition: Achondroplasia Age Group: 5-10 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/32282831	Sources: https://pubmed.ncbi.nlm.nih.gov/32282831
25 mg single, oral Recommended Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/32282831	unhealthy, 6-10 n = 6 Health Status: unhealthy Condition: Achondroplasia Age Group: 6-10 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/32282831	Sources: https://pubmed.ncbi.nlm.nih.gov/32282831
100 mg multiple, oral (total daily dose) Recommended Dose: 100 mg Route: oral Route: multiple Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010721s063lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Vertigo Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010721s063lbl.pdf Page: p.1	Other AEs: Drowsiness... Other AEs: Drowsiness Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010721s063lbl.pdf Page: p.1

AEs

AE	Significance	Dose	Population
Drowsiness		100 mg multiple, oral (total daily dose) Recommended Dose: 100 mg Route: oral Route: multiple Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010721s063lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Vertigo Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010721s063lbl.pdf Page: p.1

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0833	http://www.3bsc.com/index/pro_info.php?id=20189
AA Blocks	AA007D5D	http://www.aablocks.com/goods/Goods/detail?id=AA007D5D
AHH Chemical co.,ltd	API-1805	http://www.ahhchemical.com/product/API-1805.html
AK Scientific, Inc. (AKSCI)	J10216	http://www.aksci.com/item_detail.php?cat=J10216
AK Scientific, Inc. (AKSCI)	R831	http://www.aksci.com/item_detail.php?cat=R831
AK Scientific, Inc. (AKSCI)	W0051	http://www.aksci.com/item_detail.php?cat=W0051
Aaron Chemicals	AR007DX5	http://www.aaronchem.com/1104-22-9
Aaron Chemicals	AR00IAUE	http://www.aaronchem.com/569-65-3
AbMole Bioscience	M3213	http://www.abmole.com/products/meclizine-dihydrochloride.html
Achemo Scientific Limited	AC-65051	http://www.achemo.com/search/?Keyword=569-65-3
Achemtek	0104-027376	http://www.achemtek.com/1104-22-9
Alfa Chemistry	AP1104229	https://reagents.alfa-chemistry.com/product/meclizine-dihydrochloride-cas-1104-22-9-1600.html
Alfa Chemistry	AP31884772	https://reagents.alfa-chemistry.com/product/meclizine-hydrochloride-cas-31884-77-2-9895.html
Alichem	139001864	http://www.alichem.com/en/products/569-65-3.html
Ambinter	Amb10843602	http://www.ambinter.com/reference/10843602
Ark Pharm	AK-54924	http://www.arkpharminc.com/products/1104-22-9.html
Aurora Fine Chemicals LLC	A24.088.326	http://online.aurorafinechemicals.com/info?ID=A24.088.326
Aurora Fine Chemicals LLC	K06.253.021	http://online.aurorafinechemicals.com/info?ID=K06.253.021
Aurora Fine Chemicals LLC	K06.994.411	http://online.aurorafinechemicals.com/info?ID=K06.994.411
Aurum Pharmatech LLC	NE58451	http://www.Aurumpharmatech.com/Product/ProductDetails/NE58451
BLD Pharm	BD137309	http://www.bldpharm.com/products/1104-22-9.html
BLD Pharm	BD137310	http://www.bldpharm.com/products/31884-77-2.html
BLD Pharm	BD137308	http://www.bldpharm.com/products/569-65-3.html
BOC Sciences	1104-22-9	https://www.bocsci.com/meclizine-2hcl-cas-1104-22-9-item-84-81622.html
BOC Sciences	31884-77-2	https://www.bocsci.com/meclizine-hydrochloride-cas-31884-77-2-item-65938.html
BOC Sciences	569-65-3	https://www.bocsci.com/meclozine-cas-569-65-3-item-345566.html
BioChemPartner	BCP02929	http://www.biochempartner.com/1104-22-9-BCP02929
BioChemPartner	BCP28339	http://www.biochempartner.com/189298-48-4-BCP28339
BioChemPartner	BCP13363	http://www.biochempartner.com/31884-77-2-BCP13363
BioCrick	BCC9017	http://www.biocrick.com/Meclizine-hydrochloride-BCC9017.html
BioSynth	J-002420	https://www.biosynth.com/en/products/all-products/products/J-002420.html
BioSynth	Q-201344	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-201344.html
CSNpharm	CSN11366	https://www.csnpharm.com/products/meclizine-dihydrochloride.html
Chem Scene	CS-2388	http://www.chemscene.com/1104-22-9.html
ChemMol	44008702	http://www.chemmol.com/chemmol/44008702.html
ChemMol	49412604	http://www.chemmol.com/chemmol/49412604.html
ChemMol	49427857	http://www.chemmol.com/chemmol/49427857.html
ChemMol	99106552	http://www.chemmol.com/chemmol/99106552.html
ChemShuttle	151551	http://www.chemshuttle.com/catalogsearch/result/?q=1104-22-9&cat=
Chemenu	CM110387	http://www.chemenu.com/products/CM110387
Chemspace	CSSB00000746775	https://chem-space.com/CSSB00000746775
Chemspace	CSSB00000753008	https://chem-space.com/CSSB00000753008
Chemspace	CSSB00015288267	https://chem-space.com/CSSB00015288267
Clearsynth	CS-O-01897	http://www.clearsynth.com/en/CS-O-01897.html
Clearsynth	CS-EB-01272	https://www.clearsynth.com/en/CSEB01272.html
Clearsynth	CS-ER-01264	https://www.clearsynth.com/en/CSER01264.html
Clearsynth	CS-P-01653	https://www.clearsynth.com/en/CSP01653.html
Combi-Blocks	QA-2598	http://www.combi-blocks.com/cgi-bin/find.cgi?QA-2598
DC Chemicals	DC7757	http://www.dcchemicals.com/product_show-_R_Meclizine.html
Debye Scientific	DB-040919	http://www.debyesci.com/cas_1104-22-9.html
Enamine	EN300-58334	https://www.enaminestore.com/catalog/EN300-58334
Enamine	EN300-71543	https://www.enaminestore.com/catalog/EN300-71543
Enamine	Z53003552	https://www.enaminestore.com/catalog/Z53003552
Finetech	FT-0603544	http://www.finetechnology-ind.com/prod/detail/pub/1104-22-9.html
Finetech	FT-0659103	http://www.finetechnology-ind.com/prod/detail/pub/31884-77-2.html
Glentham Life Sciences	GP7447	http://www.glentham.com/products/product/GP7447/
Hairui	HR131737	http://www.hairuichem.com/en/product/1104-22-9.html
Hairui	HR101508	http://www.hairuichem.com/en/product/31884-77-2.html
Hairui	HR133843	http://www.hairuichem.com/en/product/569-65-3.html
LGC Standards	LGCFOR0586.00	https://www.lgcstandards.com/US/en/p/LGCFOR0586.00
LGC Standards	MM0586.00-0250	https://www.lgcstandards.com/US/en/p/MM0586.00-0250
Lab Network	LN00174195	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00174195
Lab Network	LN01796008	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01796008
Matrix Scientific	75920	https://www.matrixscientific.com/075920.html
MedChem Express	HY-B0349	https://www.medchemexpress.com/Meclizine-dihydrochloride.html
MolPort	MolPort-002-069-043	https://www.molport.com/shop/molecule-link/MolPort-002-069-043
MolPort	MolPort-003-666-221	https://www.molport.com/shop/molecule-link/MolPort-003-666-221
MolPort	MolPort-019-995-743	https://www.molport.com/shop/molecule-link/MolPort-019-995-743
MuseChem	A000946	https://www.musechem.com/product/A000946.html
OChem	30709	http://www.ocheminc.com/index.php?act=psearch&pid=104M229
OChem	12500	http://www.ocheminc.com/index.php?act=psearch&pid=569M653
Oakwood	79238	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=64412&ExtHyperLink=1
Parchem	29350	http://www.parchem.com/chemical-supplier-distributor/Meclizine-019350.aspx
Parchem	29352	http://www.parchem.com/chemical-supplier-distributor/Meclizine-Hydrochloride-019352.aspx
Parchem	29356	http://www.parchem.com/chemical-supplier-distributor/Meclozine-019356.aspx
Selleck Chemicals	S1986	http://www.selleckchem.com/products/meclizine-dihydrochloride.html
Sigma-Aldrich	PH009750_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/ph009750
Sigma-Aldrich	M0220000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/m0220000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S534869	http://www.smolecule.com/products/s534869
Smolecule	S573626	https://www.smolecule.com/products/s573626
TCI (Tokyo Chemical Industry)	M2755	http://www.tcichemicals.com/eshop/en/us/commodity/M2755/index.html
THE BioTek	bt-274528	https://www.thebiotek.com/product/inhibitors/bt-274528
Tocris	4245	https://www.tocris.com/products/meclizine-dihydrochloride_4245
Vesino Industrial Co Ltd	VA11241	http://www.vsnchem.com/goto/product/22579/
VladaChem	VL274637-25G	https://www.vladachem.com/product.php?products=1104-22-9
Yuhao Chemical	XJ1544	http://www.chemyuhao.com/1104-22-9.html
Yuhao Chemical	JZ3796	http://www.chemyuhao.com/569-65-3.html
abcr GmbH	AB349167	http://www.abcr.de/shop/en/AB349167
abcr GmbH	AB505723	http://www.abcr.de/shop/en/AB505723
eNovation Chemicals	D523825	https://www.enovationchem.com/ProductDetails.asp?ProductID=D523825
eNovation Chemicals	D618485	https://www.enovationchem.com/ProductDetails.asp?ProductID=D618485
iChemical	EBD32645	http://www.ichemical.com/chemicals/cas-1104-22-9
iChemical	EBD8359	http://www.ichemical.com/chemicals/cas-569-65-3
mcule	MCULE-4211025798	https://mcule.com/MCULE-4211025798/
mcule	MCULE-6706083805	https://mcule.com/MCULE-6706083805
mcule	MCULE-7463916552	https://mcule.com/MCULE-7463916552/

PubMed

Title	Date	PubMed
Drug-induced extrapyramidal signs in chronic liver disease--a case report.	1977	872535
Clofibrate myopathy: a case report and a review of the literature.	1986 Feb	3515563
Memory loss, confusion, and disorientation in an elderly woman taking meclizine.	1987 May	3571791
Central nervous system effects of meclizine and dimenhydrinate: evidence of acute tolerance to antihistamines.	1992 Nov	1474173
Pentoxifylline-induced musical hallucinations.	1993 Aug	8351028
Spectrophotometric determination of meclozine HCl and papaverine HCl in their pharmaceutical formulations.	2002 Apr 15	11929681
Discovery of molecular mechanisms of neuroprotection using cell-based bioassays and oligonucleotide arrays.	2002 Oct 29	12388792
Delivery outcome after the use of meclozine in early pregnancy.	2003	12952140
Spectrophotometric and LC determination of two binary mixtures containing pyridoxine hydrochloride.	2003 Jun 1	12763537
Relationship between vitamin use, smoking, and nausea and vomiting of pregnancy.	2003 Oct	12956841
Auditory hallucinations elicited by combined meclizine and metaxalone use at bedtime.	2004 Nov	15454584
Effects of drug countermeasures for space motion sickness on working memory in humans.	2004 Nov-Dec	15451046
Meclizine is an agonist ligand for mouse constitutive androstane receptor (CAR) and an inverse agonist for human CAR.	2004 Oct	15272053
Use of antiemetic drugs during pregnancy in Sweden.	2005 Dec	16328314
Withdrawal symptoms after discontinuation of transdermal scopolamine therapy: treatment with meclizine.	2009 Nov 15	19890085
Multi-species analyses of direct activators of the constitutive androstane receptor.	2011 Oct	21778469
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Vertigo -25 to 100 mg orally per day in divided doses Usual Adult Dose for Motion Sickness -Initial Dose: 25 to 50 mg orally 1 hour before travel -Maintenance Dose: Repeat dose every 24 hours if needed

Route of Administration: Oral

In Vitro Use Guide

50 uM meclizine inhibited respiratory growth of human skin fibroblasts

Name

Type

Language

MECLIZINE

Common Name

English

meclozine [INN]

Common Name

English

1-(P-CHLORO-.ALPHA.-PHENYLBENZYL)-4-(M-METHYLBENZYL)PIPERAZINE

Common Name

English

MECLIZINE [MI]

Common Name

English

NSC-169189

Code

English

MECLIZINE [VANDF]

Common Name

English

Meclozine [WHO-DD]

Common Name

English

MECLOZINE

Official Name

English

MECLIZINE [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29578