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Details

Stereochemistry RACEMIC
Molecular Formula C25H27ClN2.2ClH
Molecular Weight 463.8709
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MECLIZINE HYDROCHLORIDE ANHYDROUS

SMILES

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

InChI

InChIKey=VCTHNOIYJIXQLV-UHFFFAOYSA-N
InChI=1S/C25H27ClN2.2ClH/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;2*1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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

1.33565763E12
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

1.33565763E12
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
Central nervous system effects of meclizine and dimenhydrinate: evidence of acute tolerance to antihistamines.
1992 Nov
Pentoxifylline-induced musical hallucinations.
1993 Aug
Discovery of molecular mechanisms of neuroprotection using cell-based bioassays and oligonucleotide arrays.
2002 Oct 29
Delivery outcome after the use of meclozine in early pregnancy.
2003
Spectrophotometric and LC determination of two binary mixtures containing pyridoxine hydrochloride.
2003 Jun 1
Relationship between vitamin use, smoking, and nausea and vomiting of pregnancy.
2003 Oct
Effects of drug countermeasures for space motion sickness on working memory in humans.
2004 Nov-Dec
Meclizine is an agonist ligand for mouse constitutive androstane receptor (CAR) and an inverse agonist for human CAR.
2004 Oct
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
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
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:13:40 UTC 2021
Edited
by admin
on Fri Jun 25 21:13:40 UTC 2021
Record UNII
L997QXC9J1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MECLIZINE HYDROCHLORIDE ANHYDROUS
Common Name English
1-(P-CHLORO-.ALPHA.-PHENYLBENZYL)-4-(M-METHYLBENZYL)PIPERAZINE DIHYDROCHLORIDE
Common Name English
1-((RS)-(4-CHLOROPHENYL)PHENYLMETHYL)-4-((3-METHYLPHENYL)METHYL)PIPERAZINE DIHYDROCHLORIDE
Systematic Name English
MECLOZINE DIHYDROCHLORIDE [EP MONOGRAPH]
Common Name English
MECLIZINE DIHYDROCHLORIDE ANHYDROUS
Common Name English
NSC-28728
Code English
MECLOZINE HYDROCHLORIDE [WHO-DD]
Common Name English
MECLOZINE DIHYDROCHLORIDE
EP  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
Code System Code Type Description
CAS
36236-67-6
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
NON-SPECIFIC STOICHIOMETRY
EVMPD
SUB03109MIG
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
PRIMARY
ECHA (EC/EINECS)
252-932-4
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
NON-SPECIFIC STOICHIOMETRY
NCI_THESAURUS
C77438
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
PRIMARY
CAS
1104-22-9
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
PRIMARY
PUBCHEM
64713
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
PRIMARY
FDA UNII
L997QXC9J1
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
PRIMARY
ECHA (EC/EINECS)
214-164-8
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
PRIMARY
EPA CompTox
1104-22-9
Created by admin on Fri Jun 25 21:13:40 UTC 2021 , Edited by admin on Fri Jun 25 21:13:40 UTC 2021
PRIMARY
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