MECLIZINE

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

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

Molecular Formula	C25H27ClN2
Molecular Weight	390.948
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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	Inhibitor 8,297
Pregnane X receptor 35	Agonist 2,678
Ethanolamine-phosphate cytidylyltransferase 8	Inhibitor 8,297	31.0 µM [Ki]
Histamine H1 receptor 315	Antagonist 2,778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Motion sickness 43	Primary		Approved 8,429	ANTIVERT
Vertigo 17	Primary		Approved 8,429	ANTIVERT

C_max

Value	Dose	Analyte	Population
99.43 ng/mL	25 mg single, oral	MECLIZINE plasma	Homo sapiens
99.43 ng/mL	25 mg single, oral	MECLIZINE plasma	Homo sapiens
130 ng/mL	25 mg single, oral	MECLIZINE plasma	Homo sapiens
223 ng/mL	25 mg 2 times / day multiple, oral	MECLIZINE plasma	Homo sapiens
149 ng/mL	25 mg single, oral	MECLIZINE plasma	Homo sapiens
131.3 ng/mL	25 mg 1 times / day steady-state, oral	MECLIZINE plasma	Homo sapiens
210.8 ng/mL	25 mg 2 times / day steady-state, oral	MECLIZINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
564.03 ng × h/mL	25 mg single, oral	MECLIZINE plasma	Homo sapiens
564.03 ng × h/mL	25 mg single, oral	MECLIZINE plasma	Homo sapiens
671 ng × h/mL	25 mg single, oral	MECLIZINE plasma	Homo sapiens
2030 ng × h/mL	25 mg single, oral	MECLIZINE plasma	Homo sapiens
656 ng × h/mL	25 mg 1 times / day steady-state, oral	MECLIZINE plasma	Homo sapiens
1891 ng × h/mL	25 mg 2 times / day steady-state, oral	MECLIZINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
5.24 h	25 mg single, oral	MECLIZINE plasma	Homo sapiens
5.24 h	25 mg single, oral	MECLIZINE plasma	Homo sapiens
8.5 h	25 mg single, oral	MECLIZINE plasma	Homo sapiens
3.6 h	25 mg single, oral	MECLIZINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
100 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT
50 mg single, oral Recommended	healthy, ADULT	Other AEs: Drowsiness...
25 mg 2 times / day multiple, oral Recommended	unhealthy, 5-10
25 mg single, oral Recommended	unhealthy, 6-10
100 mg multiple, oral Recommended	unhealthy	Other AEs: Drowsiness...

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AEs

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AE	Significance	Dose	Population
Drowsiness	30%	50 mg single, oral Recommended	healthy, ADULT
Drowsiness		100 mg multiple, oral Recommended	unhealthy

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Sourcing

Sourcing

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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
Aaron Chemicals	AR007DX5	http://www.aaronchem.com/1104-22-9
Aaron Chemicals	AR00IAUE	http://www.aaronchem.com/569-65-3
abcr GmbH	AB349167	http://www.abcr.de/shop/en/AB349167

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PubMed

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Title	Date	PubMed
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

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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