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Meclizine

HCID 4034
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
163837-49-8
Standard SMILES
Cc1cccc(CN2CCN(C(c3ccccc3)c3ccc(Cl)cc3)CC2)c1
InChIKey
OCJYIGYOJCODJL-UHFFFAOYSA-N
Molecular formula
C25H27ClN2
Average molar mass
390.9 g/mol
Monoisotopic mass
390.1862766

Overview

Meclizine is a diarylmethane.

Names & identifiers

Preferred name
Meclizine
IUPAC
1-[(4-chlorophenyl)-phenylmethyl]-4-[(3-methylphenyl)methyl]piperazine
English name
Meclozine
Molecular formula
C25H27ClN2
Molecular weight
390.95

Names & synonyms

meclizineMeclozine569-65-3ParachloramineNavicalmSuprimalVomisseisRavelonBonadettesSea-LegsChiclidaItinerol
Show more names
BonineMarexSabariSubariAncolanAncolon
MonamineSiguranTravelonNeo-suprimalNeo-suprimelUCB 1701-[(4-chlorophenyl)-phenylmethyl]-4-[(3-methylphenyl)methyl]piperazine1-[(4-chlorophenyl)(phenyl)methyl]-4-[(3-methylphenyl)methyl]piperazine

Database identifiers

CAS
163837-49-8、569-65-3
PubChem CID
4034
DTXSID
DTXSID0023242
ChEMBL
CHEMBL1623
ChEBI
CHEBI:6709
UNII
3L5TQ84570
EC Number
209-323-3
Nikkaji
J6.532C

Properties

Computed structural properties

XLogP
5.8
Topological polar surface area
6.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
5
Heavy atoms
28
Formal charge
0
Complexity
447

Experimental & physicochemical properties

DrugsPharmaceuticals
LogP · 2 items

5.8

4.22

Solubility · 4 items

0.1g/100mL

FREELY SOL IN CHLOROFORM, PYRIDINE; SLIGHLY SOL IN DIL ACIDS, ALCOHOL; PRACTICALLY INSOL IN WATER, ETHER /MECLIZINE DIHYDROCHLORIDE/

FREELY SOL IN METHYLACETAMIDE, PYRIDINE, CHLOROFORM, ACID-ALCOHOL-WATER MIXT /MECLIZINE HYDOCHLORIDE/

1.03e-03 g/L

Human Drugs · 2 items

Breast Feeding; Lactation; Milk, Human; Antiemetics; Antihistamines; Anti-Allergic Agents

Pharmaceuticals

Boiling Point230 °C @ 2 MM HG
Melting Point217-224
Physical DescriptionSolid
Ionization Efficiency · 6 items

Positive

4.57

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Regulatory InformationMeclozine: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Piperazine, 1-[(4-chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]-: Environment tier I assessment
FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Hazard Classes and CategoriesEye Irrit. 2 (100%)

Safety & protection

Storage ConditionsMeclizine hydrochloride preparations should be stored at a temp less than 40 °C, preferably between 15-30 °C; the conventional tablets should be stored in well-closed containers. /Meclizine hydrochloride/
Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Chemistry & industry

Pharmacology

ATC Code · 3 items

R06AE05

R - Respiratory system

QR - Respiratory system

Protein BindingThere is limited data on the protein binding profile of meclizine.
Pharmacodynamics · 1 item

Meclizine works on the higher centres of the brain to reduce nausea, vomiting, or vertigo. It is effective against nausea and vomiting arising from many causes, including motion sickness and disorders affecting the vestibular system. The onset of action of meclizine is about 1 hour, with effects lasting between 8 to 24 hours. Meclizine is reported to cause drowsiness due to its anticholinergic actions.

Mechanism of Action · 3 items

Vomiting is a centrally regulated reflex mechanism that initiates from the vomiting center and the chemoreceptor trigger zone (CTZ) located in the medulla. Motion sickness is also regulated by CTZ. The blood-brain barrier near the CTZ is relatively permeable to circulating mediators and CTZ can transmit impulses to vomiting center located in the brainstem. Different receptors responding to different factors, including histamine, 5-HT, enkephalins, substance P, and dopamine, are expressed along the brainstem to activate respective pathways and contribute to the control of vomiting. Histamine H1 receptors are expressed on the vestibular nuclei and nucleus of the solitary tract (NTS) that are activated by motion sickness and stimuli from the pharynx and stomach. When activated, H1 receptor signaling from these nuclei is transmitted to the CTZ and vomiting centre. Through its antagonistic action on the H1 receptors, meclizine primarily works by inhibiting signaling pathway transduction through histaminergic neurotransmission from the vestibular nuclei and NTS to the CTZ and medullary vomiting center. Meclizine may also decrease the labyrinth excitability and vestibular stimulation.

HI-RECEPTOR BLOCKERS HAVE ESTABLISHED & VALUED PLACE IN SYMPTOMATIC TREATMENT OF...ALLERGIC DISEASES, IN WHICH THEIR USEFULNESS...ATTRIBUTABLE TO THEIR ANTAGONISM OF HISTAMINE. ...CENTRAL PROPERTIES OF SOME...ARE OF...THERAPEUTIC VALUE...IN SUPPRESSING MOTION SICKNESS. /H1-RECEPTOR BLOCKERS/

Meclizine has CNS depressant, anticholinergic, antiemetic, antispasmodic, and local anesthetic effects in addition to antihistaminic activity. The drug depresses labyrinth excitability and conduction in vestibular-cerebellar pathways. The antiemetic and antimotion-sickness actions of meclizine result, at least in part, from its central anticholinergic and CNS depressant properties.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Collision Cross Section · 2 items

208.2 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

184.22 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Other Experimental Properties · 2 items

HAS SLIGHT ODOR; TASTELESS; MELTS BETWEEN 217 & 224 °C /MECLIZINE HYDROCHLORIDE/

WHITE OR SLIGHTLY YELLOWISH, CRYSTALLINE POWDER /MECLIZINE HYDROCHLORIDE/

Physicochemical properties

Boiling point
2 · bp2 230°
Density
1.0318 · 1.0318 (rough estimate)
refractive index
1.594 · 1.5940 (estimate)
storage temp.
2 · 2-8°C
pka
2.05 · pKa 2.05(H2O,t =25,I=0.0051(NaCl)) (Uncertain)
BCS Class
2 · 2
CAS DataBase Reference
569 · 569-65-3(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
3 L5TQ84570 · 3L5TQ84570
NCI Drug Dictionary
Bonine
ATC code
6 AE05,R06AE55 · R06AE05,R06AE55
NIST Chemistry Reference
Meclizine(569-65-3)
EPA Substance Registry System
Meclizine (569-65-3)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
TSCA
TSCA listed
Hazardous Substances Data
569 · 569-65-3(Hazardous Substances Data)

Toxicology

HepatotoxicityDespite widespread use, meclizine has not been linked to liver test abnormalities or to clinically apparent liver injury. The reason for its safety may relate to low daily dose and limited duration of use.
Adverse Effects · 1 item

Common adverse effects of patients taking meclizine include drowsiness, urinary retention, dry mouth, headache, fatigue, and vomiting. On rare occasions, there have been reports of blurred vision and anaphylactic reactions when taking meclizine.

Exposure RoutesOral. Well absorbed
Toxicity Summary · 2 items

There are no specific antidotes available for meclizine overdose. Treatment is primarily supportive and focused on symptoms. Symptoms of an overdose may include signs of CNS depression such as drowsiness, seizures, and coma. Hypotension can occur, but it is more likely to be seen in older people. The anticholinergic effects and CNS stimulation of an overdose in children can present with hallucinations, seizures, and insomnia. With recent ingestion, induce emesis or perform gastric lavage to prevent further drug absorption. Activated charcoal is also an option. There is no known antidote for meclizine, but physostigmine can help to counter the systemic anticholinergic effects of meclizine.

Along with its actions as an antagonist at H<sub>1</sub>-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.

Signs and SymptomsSymptoms of overdose include drowsiness and anticholinergic effects.
Human Toxicity Excerpts · 5 items

Central excitaton is also a striking feature of poisoning, which not uncommonly results in convulsions, particularly in infants. /H1 Antagonists/

In acute poisoning with H1 antagonists, their central excitatory effects constitute the greatest danger. The syndrome includes hallucinations, excitement, ataxia, incoordination, athetosis, and convulsions. Fixed, dilated pupils with a flushed face, together with sinus tachycardia, urinary retention, dry mouth, and fever, lend the syndrome a remarkable similarity to that of atropine poisoning. Terminally, there is deepening coma with cardiorespiratory collapse and death, usually within 12 to 18 hours. /H1 Antagonists/

SIDE EFFECT WITH HIGHEST INCIDENCE, &...COMMON TO ALL DRUGS IN THIS GROUP, IS SEDATION. ... OTHER UNTOWARD REACTIONS REFERABLE TO CENTRAL ACTIONS INCL DIZZINESS, TINNITUS, LASSITUDE, INCOORDINATION, FATIGUE, BLURRED VISION, DIPLOPIA, EUPHORIA, NERVOUSNESS, INSOMNIA & TREMORS. /H1 ANTAGONISTS/

...FREQUENT SIDE EFFECTS INVOLVE DIGESTIVE TRACT & INCL LOSS OF APPETITE, NAUSEA, VOMITING, EPIGASTRIC DISTRESS & CONSTIPATION OR DIARRHEA. /H1 ANTAGONISTS/

For more Human Toxicity Excerpts (Complete) data for MECLIZINE (10 total), please visit the HSDB record page.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 items

Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)

meclizine

Antivert®

Antihistamines

Not Applicable

no-DILI-concern

Non-Human Toxicity Excerpts · 2 items

.../IN 1963 WAS 1ST REPORT OF/ PRODUCTION OF CLEFT PALATE BY HIGH DOSAGE OF MECLIZINE IN RATS... /IT WAS SUGGESTED/ THAT NORCHLORCYCLIZINE, WHICH IS A METABOLITE.../OF MECLIZINE/ IS PROBABLE ACTIVE FORM OF TERATOGEN.

TERATOGENICITY HAS BEEN REPORTED IN SWINE, MICE, RABBITS, RATS & DOGS.

Effects During Pregnancy and Lactation · 2 items

◉ Summary of Use during Lactation

◈ What is meclizine?

Toxicity DataLD50: 1600 mg/kg (oral) (A701) LD50: 659 mg/kg (i.p.) (A701)
EPA Human Health Benchmarks for Pharmaceuticals · 6 items

Meclizine

0.6

2.5

The recommended dosage is 25 mg to 100 mg daily administered orally, in divided doses, depending upon clinical response.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 25 mg/day, Lowest Therapeutic Dose (LTD): 0.3 mg/kg-day, and Screening Dose: 0.0001 mg/kg-day.

30-Dec-20

Regulatory information

FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Safety data

tsca
TSCA listed
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P305+P351+P338
Hazardous Substances Data
569-65-3(Hazardous Substances Data)
Biological Half-Life · 2 items

Meclizine has a plasma elimination half-life of about 5-6 hours in humans.

The drug has a plasma half-life of 6 hr. /Meclizine hydrochloride/

Metabolism/Metabolites · 4 items

There is limited human data on meclizine metabolism. According to the findings of _in vitro_ studies, meclizine may undergo aromatic hydroxylation or benzylic oxidation mediated by the hepatic CYP2D6 enzyme.

OXIDATIVE N-DEALKYLATION IS MAIN METAB PATHWAY OF BENZHYDROLPIPERAZINES... NORCHLORCYCLIZINE IS...MAJOR METABOLITE OF MECLIZINE.

The metabolic fate of meclizine in humans in unknown. In rats, meclizine is metabolized (probably in the liver) to norchlorcyclizine. This metabolite is distributed throughout most body tissues and crosses the placenta.

Hepatic Half Life: 6 hours

FDA Pharmacological Classification · 6 items

3L5TQ84570

MECLIZINE

Established Pharmacologic Class [EPC] - Antiemetic

Physiologic Effects [PE] - Emesis Suppression

Meclizine is an Antiemetic. The physiologic effect of meclizine is by means of Emesis Suppression.

MECLIZINE

MeSH Pharmacological Classification · 4 items

Drugs used to prevent NAUSEA or VOMITING.

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.

Drugs that bind to but do not activate CHOLINERGIC RECEPTORS, thereby blocking the actions of ACETYLCHOLINE or cholinergic agonists.

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)

Absorption, Distribution and Excretion · 6 items

Most histamine H1 antagonists are reported to be readily absorbed following oral administration. Upon oral administration, the time to reach peak plasma concentrations (Cmax) of meclizine is about 3 hours post-dose, with the value ranging from 1.5 to 6 hours.

Meclizine is excreted in the urine as metabolites and in the feces as unchanged drug.

The volume of distribution of meclizine in humans has not been fully studied. It is proposed that meclizine may be excreted into breast milk.

There is limited data on the clearance of meclizine.

BENZHYDROLPIPERAZINES & THEIR N-DEALKYLATION PRODUCTS ARE DISTRIBUTED IN ALL TISSUES OF RATS & TRANSFERRED TO FETUS.

The drug is excreted in feces unchanged and in urine as norchlorcyclizine. /Meclizine hydrochloride/

Cellular LocationsMembrane
Metabolite PathwaysMeclizine H1-Antihistamine Action

Uses & manufacturing

Uses · 4 items

MEDICATION (VET)

MEDICATION

Use (kg) in Switzerland (2009): >25

For the prevention and treatment of nausea, vomiting, or dizziness associated with motion sickness.

Methods of ManufacturingFormed by condensing N-(m-methylbenzyl)piperizine with p-chlorobenzylhydryl chloride in the presence of triethylamine.
Formulations/PreparationsUCB 5062, ANCOLAN, BONAMINE, BONINE, CALMONAL, DIADRIL, HISTAMETIZINE, NAVICALM, NEO-ISTAFENE, PEREMESIN, POSTAFEN SUPP, SABARI, SEA-LEGS & VERITAB. /DIHYDROCHLORIDE/
Use Classification · 2 items

Pharmaceuticals

Pharmaceuticals -> Antihistamines

General Manufacturing InformationPiperazine, 1-[(4-chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]-: INACTIVE

Applications

UsesAnti-emetic.

UsesMeclizine actively affects the vomiting center and is used for vomiting and diarrhea. Synonyms of this drug are antivert, bonine, lamin, roclizin, and vertol.

Upstream & downstream products

Upstream raw materials

DiphenylBenzyl chlorideCHLORCYCLIZINE1-BENZHYDRYLPIPERAZINE1-BenzylpiperazineSodium amideHydrogen3-Methylbenzyl chloride

Additional notes

DefinitionChEBI: Meclizine is a diarylmethane.