U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of MECLIZINE

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
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

Curator's Comment: central nervous system depressant

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q922E4
Gene ID: 68671.0
Gene Symbol: Pcyt2
Target Organism: Mus musculus (Mouse)
31.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
99.43 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
564.03 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.24 h
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

Doses

DosePopulationAdverse 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:
unhealthy, 5-10
n = 6
Health Status: unhealthy
Condition: Achondroplasia
Age Group: 5-10
Sex: M+F
Population Size: 6
Sources:
25 mg single, oral
Recommended
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
unhealthy, 6-10
n = 6
Health Status: unhealthy
Condition: Achondroplasia
Age Group: 6-10
Sex: M+F
Population Size: 6
Sources:
100 mg multiple, oral (total daily dose)
Recommended
Dose: 100 mg
Route: oral
Route: multiple
Dose: 100 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Vertigo
Sources: Page: p.1
Other AEs: Drowsiness...
AEs

AEs

AESignificanceDosePopulation
Drowsiness
100 mg multiple, oral (total daily dose)
Recommended
Dose: 100 mg
Route: oral
Route: multiple
Dose: 100 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Vertigo
Sources: Page: p.1
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Drug-induced extrapyramidal signs in chronic liver disease--a case report.
1977
Clofibrate myopathy: a case report and a review of the literature.
1986 Feb
Memory loss, confusion, and disorientation in an elderly woman taking meclizine.
1987 May
Pentoxifylline-induced musical hallucinations.
1993 Aug
Relationship between vitamin use, smoking, and nausea and vomiting of pregnancy.
2003 Oct
Auditory hallucinations elicited by combined meclizine and metaxalone use at bedtime.
2004 Nov
Use of antiemetic drugs during pregnancy in Sweden.
2005 Dec
Withdrawal symptoms after discontinuation of transdermal scopolamine therapy: treatment with meclizine.
2009 Nov 15
Multi-species analyses of direct activators of the constitutive androstane receptor.
2011 Oct
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Patents

Patents

Sample Use Guides

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
50 uM meclizine inhibited respiratory growth of human skin fibroblasts
Name Type Language
MECLIZINE
HSDB   MI   VANDF  
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
INN   WHO-DD  
INN  
Official Name English
MECLIZINE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
WHO-ATC R06AE05
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
WHO-ATC R06AE55
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
WHO-VATC QR06AE55
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
LIVERTOX NBK547895
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
WHO-VATC QR06AE05
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
NDF-RT N0000178372
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
NCI_THESAURUS C267
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NDF-RT N0000009034
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
NDF-RT N0000009034
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
Code System Code Type Description
RXCUI
6676
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00737
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PRIMARY
PUBCHEM
4034
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PRIMARY
WIKIPEDIA
MECLOZINE
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
PRIMARY
ChEMBL
CHEMBL1623
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PRIMARY
EVMPD
SUB08685MIG
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PRIMARY
NCI_THESAURUS
C61610
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PRIMARY
LACTMED
Meclizine
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PRIMARY
FDA UNII
3L5TQ84570
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PRIMARY
DRUG CENTRAL
1649
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PRIMARY
NSC
169189
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PRIMARY
SMS_ID
100000081967
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PRIMARY
MERCK INDEX
m7118
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
PRIMARY Merck Index
IUPHAR
2757
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PRIMARY
ECHA (EC/EINECS)
209-323-3
Created by admin on Fri Dec 15 17:17:01 GMT 2023 , Edited by admin on Fri Dec 15 17:17:01 GMT 2023
PRIMARY
DAILYMED
3L5TQ84570
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PRIMARY
MESH
D008468
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PRIMARY
HSDB
3113
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PRIMARY
INN
204
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PRIMARY
EPA CompTox
DTXSID0023242
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PRIMARY
CAS
569-65-3
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PRIMARY