MECLIZINE

US Approved OTC

First approved in 1954

Details

Stereochemistry	RACEMIC
Molecular Formula	C25H27ClN2
Molecular Weight	390.9491
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cc1cccc(c1)CN2CCN(CC2)C(c3ccccc3)c4ccc(cc4)Cl

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	390.9491
Charge	0
Count

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

Description
Sources: http://www.drugbank.ca/drugs/DB00737
Curator's Comment:: 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	Condition	Potency
Cytochrome P450 3A4 116 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26239802	Inhibitor 7701
Pregnane X receptor 34 Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26239802	Agonist 2456
Ethanolamine-phosphate cytidylyltransferase 8 Target ID: Q922E4 Gene ID: 68671 Gene Symbol: Pcyt2 Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24142790	Inhibitor 7701		31 µM [Ki]
Histamine H1 receptor 300 Target ID: CHEMBL231 Sources: http://www.drugbank.ca/drugs/DB00737	Antagonist 2577	Motion sickness Vertigo

Conditions

Condition	Modality	Targets	Highest Phase	Product
Motion sickness 44 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/010721s058lbl.pdf	Primary	Histamine H1 receptor	Approved 7997	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 1335657600000
Vertigo 17 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/010721s058lbl.pdf	Primary	Histamine H1 receptor	Approved 7997	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 1335657600000

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 Health Status: unhealthy Age Group: 5-10 Sex: M+F 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 Health Status: unhealthy Age Group: 6-10 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/32282831	Sources: https://pubmed.ncbi.nlm.nih.gov/32282831
100 mg multiple, oral Recommended Dose: 100 mg Route: oral Route: multiple Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010721s063lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010721s063lbl.pdf	Other AEs: Drowsiness... Other AEs: Drowsiness Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010721s063lbl.pdf

AEs

AE	Significance	Dose	Population
Drowsiness		100 mg multiple, oral Recommended Dose: 100 mg Route: oral Route: multiple Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010721s063lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010721s063lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
PubChem	173612	https://pubchem.ncbi.nlm.nih.gov/compound/173612
PubChem	4034	https://pubchem.ncbi.nlm.nih.gov/compound/4034
PubChem	49800000	https://pubchem.ncbi.nlm.nih.gov/compound/49800000
PubChem	64713	https://pubchem.ncbi.nlm.nih.gov/compound/64713
PubChem	91981561	https://pubchem.ncbi.nlm.nih.gov/compound/91981561
PubChem	92303	https://pubchem.ncbi.nlm.nih.gov/compound/92303

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

Route of Administration: Oral

In Vitro Use Guide

50 uM meclizine inhibited respiratory growth of human skin fibroblasts

Substance Class	Chemical Created by `admin` on `Sat Jun 26 06:53:00 UTC 2021` Edited by `admin` on `Sat Jun 26 06:53:00 UTC 2021`
Record UNII	3L5TQ84570
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MECLIZINE

Common Name

English

MECLOZINE [WHO-DD]

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

Official Name

English

MECLIZINE [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29578