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Details

Stereochemistry RACEMIC
Molecular Formula C25H27ClN2.2ClH.H2O
Molecular Weight 481.8862
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MECLIZINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=KDLHYOMCWBWLMM-UHFFFAOYSA-N
InChI=1S/C25H27ClN2.2ClH.H2O/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;1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
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 ( + / - )

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

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
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
Central nervous system effects of meclizine and dimenhydrinate: evidence of acute tolerance to antihistamines.
1992 Nov
Pentoxifylline-induced musical hallucinations.
1993 Aug
Spectrophotometric determination of meclozine HCl and papaverine HCl in their pharmaceutical formulations.
2002 Apr 15
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
Auditory hallucinations elicited by combined meclizine and metaxalone use at bedtime.
2004 Nov
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
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
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:04:10 UTC 2021
Edited
by admin
on Fri Jun 25 21:04:10 UTC 2021
Record UNII
HDP7W44CIO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MECLIZINE HYDROCHLORIDE
JAN   ORANGE BOOK   USP   VANDF  
Common Name English
MECLIZINE DIHYDROCHLORIDE MONOHYDRATE, (+/-)-
Common Name English
UCB-5062
Code English
MECLIZINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
MECLIZINE DIHYDROCHLORIDE MONOHYDRATE
MI  
Common Name English
BONINE
Brand Name English
MECLIZINE HYDROCHLORIDE [USP-RS]
Common Name English
PIPERAZINE, 1-((4-CHLOROPHENYL)PHENYLMETHYL)-4-((3-METHYLPHENYL)METHYL)-, DIHYDROCHLORIDE, MONOHYDRATE
Common Name English
MECLIZINE HCL
Common Name English
MECLIZINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
ANCOLAN
Brand Name English
AGYRAX
Brand Name English
BONAMINE
Common Name English
MECLIZINE DIHYDROCHLORIDE MONOHYDRATE [MI]
Common Name English
POSTAFEN
Brand Name English
MECLIZINE HYDROCHLORIDE [VANDF]
Common Name English
ANTIVERT
Brand Name English
NSC-757094
Code English
MECLOZINE HYDROCHLORIDE MONOHYDRATE [WHO-DD]
Common Name English
1-(P-CHLORO-.ALPHA.-PHENYLBENZYL)-4-(M-METHYLBENZYL)PIPERAZINE DIHYDROCHLORIDE MONOHYDRATE
Common Name English
MECLIZINE HYDROCHLORIDE [JAN]
Common Name English
(+/-)-MECLIZINE DIHYDROCHLORIDE MONOHYDRATE
Common Name English
MECLOZINE HYDROCHLORIDE MONOHYDRATE
WHO-DD  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
NCI_THESAURUS C267
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
CFR 21 CFR 336.50
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
CFR 21 CFR 336.10
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
Code System Code Type Description
USP_CATALOG
1377029
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY USP-RS
RXCUI
82041
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY RxNorm
USP_CATALOG
1377009
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY USP-RS
PUBCHEM
173612
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY
MERCK INDEX
M7118
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY Merck Index
FDA UNII
HDP7W44CIO
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY
NCI_THESAURUS
C29245
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY
CAS
31884-77-2
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY
DRUG BANK
DBSALT000678
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL1623
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY
EVMPD
SUB35563
Created by admin on Fri Jun 25 21:04:10 UTC 2021 , Edited by admin on Fri Jun 25 21:04:10 UTC 2021
PRIMARY
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