Meclizine

HCID 178805770

기본 정보

CAS
163837-50-1
표준 SMILES
Cc1cccc(CN2CCN(C(c3ccccc3)c3ccc(Cl)cc3)CC2)c1
InChIKey
OCJYIGYOJCODJL-UHFFFAOYSA-N
분자식
C25H27ClN2
평균 분자량
390.9 g/mol

개요

Meclizine is a diarylmethane.

이름 및 식별자

우선 이름
Meclizine
IUPAC
1-[(4-chlorophenyl)-phenylmethyl]-4-[(3-methylphenyl)methyl]piperazine
영어명
mecilizine
분자식
C25H27ClN2
분자량
390.95

이름 및 동의어

meclizineMeclozine569-65-3ParachloramineNavicalmSuprimalVomisseisRavelonBonadettesSea-LegsChiclidaItinerol
이름 더 보기
MonamineSiguranTravelonNeo-suprimalNeo-suprimelUCB 1701-[(4-chlorophenyl)-phenylmethyl]-4-[(3-methylphenyl)methyl]piperazine1-[(4-chlorophenyl)(phenyl)methyl]-4-[(3-methylphenyl)methyl]piperazine

데이터베이스 식별자

CAS
163837-50-1
ChEMBL
CHEMBL1623
ChEBI
CHEBI:6709
UNII
3L5TQ84570
EC Number
209-323-3
Nikkaji
J6.532C

물성

구조 계산 물성

XLogP
5.8
극성 표면적
6.5 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
5
무거운 원자 수
28

실험 및 물리화학적 성질

DrugsPharmaceuticals
LogP · 2건

5.8

4.22

Solubility · 4건

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 · 2건

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

Pharmaceuticals

Boiling Point230 °C @ 2 MM HG
Melting Point217-224

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

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 · 1건

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%)

안전 및 보호

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 · 1건

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.

독성 정보

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 · 1건

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 · 2건

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 · 5건

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.

규제 정보

FDA Requirements · 1건

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).

화학 및 산업

약리 정보

ATC Code · 3건

R06AE05

R - Respiratory system

QR - Respiratory system

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

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 · 3건

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.

Biological Half-Life · 2건

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 · 4건

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

용도 및 제조

Uses · 4건

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 · 2건

Pharmaceuticals -> Antihistamines

Pharmaceuticals

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

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