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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 of MECLIZINE

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

Description
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

Curator's Comment:: central nervous system depressant

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q922E4
Gene ID: 68671
Gene Symbol: Pcyt2
Target Organism: Mus musculus (Mouse)
31 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

1335657600000
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

1335657600000
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
Health Status: unhealthy
Age Group: 5-10
Sex: M+F
Sources:
25 mg single, oral
Recommended
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
unhealthy, 6-10
Health Status: unhealthy
Age Group: 6-10
Sex: M+F
Sources:
100 mg multiple, oral
Recommended
Dose: 100 mg
Route: oral
Route: multiple
Dose: 100 mg
Sources:
unhealthy
Other AEs: Drowsiness...
AEs

AEs

AESignificanceDosePopulation
Drowsiness
100 mg multiple, oral
Recommended
Dose: 100 mg
Route: oral
Route: multiple
Dose: 100 mg
Sources:
unhealthy
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
Spectrophotometric determination of meclozine HCl and papaverine HCl in their pharmaceutical formulations.
2002 Apr 15
Meclizine is an agonist ligand for mouse constitutive androstane receptor (CAR) and an inverse agonist for human CAR.
2004 Oct
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
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 [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
INN   WHO-DD  
INN  
Official Name English
MECLIZINE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
WHO-ATC R06AE05
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
WHO-ATC R06AE55
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
WHO-VATC QR06AE55
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
LIVERTOX 587
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
WHO-VATC QR06AE05
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
NDF-RT N0000178372
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
NCI_THESAURUS C267
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
NDF-RT N0000009034
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
NDF-RT N0000009034
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
Code System Code Type Description
RXCUI
6676
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00737
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
PUBCHEM
4034
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
WIKIPEDIA
MECLOZINE
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
ChEMBL
CHEMBL1623
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
EVMPD
SUB08685MIG
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
NCI_THESAURUS
C61610
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
LACTMED
Meclizine
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
FDA UNII
3L5TQ84570
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
DRUG CENTRAL
1649
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
MERCK INDEX
M7118
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY Merck Index
IUPHAR
2757
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
ECHA (EC/EINECS)
209-323-3
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
MESH
D008468
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
HSDB
3113
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
INN
204
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
EPA CompTox
569-65-3
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY
CAS
569-65-3
Created by admin on Sat Jun 26 06:53:01 UTC 2021 , Edited by admin on Sat Jun 26 06:53:01 UTC 2021
PRIMARY