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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H27ClN2
Molecular Weight 390.948
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MECLIZINE, (S)-

SMILES

CC1=CC=CC(CN2CCN(CC2)[C@@H](C3=CC=CC=C3)C4=CC=C(Cl)C=C4)=C1

InChI

InChIKey=OCJYIGYOJCODJL-VWLOTQADSA-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/t25-/m0/s1

HIDE SMILES / InChI

Description

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 TargetPharmacologyConditionPotency
31.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ANTIVERT
Primary
ANTIVERT

Cmax

ValueDoseCo-administeredAnalytePopulation
99.43 ng/mL
25 mg single, oral
MECLIZINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
564.03 ng × h/mL
25 mg single, oral
MECLIZINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.24 h
25 mg single, oral
MECLIZINE plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
50 uM meclizine inhibited respiratory growth of human skin fibroblasts