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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 447
실험 및 물리화학적 성질
LogP
5.8
4.22
Solubility
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
Breast Feeding; Lactation; Milk, Human; Antiemetics; Antihistamines; Anti-Allergic Agents
Pharmaceuticals
Ionization Efficiency
Positive
4.57
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Collision Cross Section
208.2 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
182.41 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Other Experimental Properties
HAS SLIGHT ODOR; TASTELESS; MELTS BETWEEN 217 & 224 °C /MECLIZINE HYDROCHLORIDE/
WHITE OR SLIGHTLY YELLOWISH, CRYSTALLINE POWDER /MECLIZINE HYDROCHLORIDE/
안전 및 규제
GHS 분류
GHS Classification
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
FDA Requirements
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).
안전 및 보호
Disposal Methods
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
Adverse Effects
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.
Toxicity Summary
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.
Human Toxicity Excerpts
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.
Drug Induced Liver Injury
Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)
meclizine
Antivert®
Antihistamines
Not Applicable
no-DILI-concern
Non-Human Toxicity Excerpts
.../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
◉ Summary of Use during Lactation
◈ What is meclizine?
규제 정보
FDA Requirements
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
R06AE05
R - Respiratory system
QR - Respiratory system
Pharmacodynamics
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
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
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
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
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
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
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/
용도 및 제조
Uses
MEDICATION (VET)
MEDICATION
Use (kg) in Switzerland (2009): >25
For the prevention and treatment of nausea, vomiting, or dizziness associated with motion sickness.
Use Classification
Pharmaceuticals -> Antihistamines
Pharmaceuticals
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