基本情報
- CAS
486-16-8- 標準SMILES
CN(C)CCOC(c1ccc(Cl)cc1)c1ccccn1- InChIKey
OJFSXZCBGQGRNV-UHFFFAOYSA-N- 分子式
- C16H19ClN2O
- 平均分子量
- 290.79 g/mol
- 単同位体質量
- 290.1185909
概要
Carbinoxamine is an organochlorine compound that is 2-(4-chlorobenzyl)pyridine in which one of the benzylic hydrogens is substituted by 2-(dimethylamino)ethoxy group. It is an ethanolamine-type antihistamine, used as its maleate salt for treating hay fever, as well as mild cases of Parkinson's disease. It has a role as a H1-receptor antagonist, an antiparkinson drug, a muscarinic antagonist and an anti-allergic agent. It is a member of pyridines, a tertiary amino compound and a member of monochlorobenzenes.
名称と識別子
- 優先名称
- Carbinoxamine
- IUPAC
- 2-[(4-chlorophenyl)-pyridin-2-ylmethoxy]-N,N-dimethylethanamine
- 現地名
- カルビノキサミン
- 英語名
- carbinoxamine
- 分子式
- C16H19ClN2O
- 分子量
- 290.78786
名称と別名
carbinoxamine486-16-8ParacarbinoxamineAllergefonCarbinoxaminaCarbinoxaminum(+-)-CarbinoxamineCarbinoxamine basePalgic2-(p-Chloro-alpha-(2-(dimethylamino)ethoxy)benzyl)pyridine982A7M02H5Ethanamine, 2-((4-chlorophenyl)-2-pyridinylmethoxy)-N,N-dimethyl-
名称をさらに表示
カルビノキサミン2-[(4-クロロフェニル)-2-ピリジニルメトキシ]-N,N-ジメチルエタンアミン2-[p-クロロ-α-(2-ジメチルアミノエトキシ)ベンジル]ピリジン2-[p-クロロ-α-[2-(ジメチルアミノ)エトキシ]ベンジル]ピリジンN,N-ジメチル-2-[α-(2-ピリジニル)-4-クロロベンジルオキシ]エタンアミンC06871carbinoxamine USP/EP/BPCarbinoxamine (base and/or unspecified salts)2-[p-Chloro-α-(2-dimethylaminoethoxy)benzyl]pyridine2-[p-chloro-a-(2-dimethylaminoethoxy)benzyl]pyridine2-[p-Chloro-α-[2-(dimethylamino)ethoxy]benzyl]pyridine
Ethanamine, 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethyl-CHEBI:3398DTXSID4022737N,N-Dimethyl-2-(p-chloro-alpha-(2-pyridyl)benzyloxy)ethylamineArbinoxa{2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylamine{2-[(4-Chloro-phenyl)-pyridin-2-yl-methoxy]-ethyl}-dimethyl-amine(2-((4-chlorophenyl)(pyridin-2-yl)methoxy)ethyl)dimethylamine
物性
構造計算による物性
- XLogP
- 2.9
- 極性表面積
- 25.4 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 6
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 267
実験および物理化学的性質
LogP2.6
Solubility2.28e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihistamines
Pharmaceuticals
Melting Point
< 25 °C
< 25 °C
Physical DescriptionSolid
Collision Cross Section169.28 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 沸点
- 0.1 · bp0.1 158-162°
- 酸解離定数(Pka)
- 8.1 · pKa 8.1 (Uncertain)
- NISTの化学物質情報
- Carbinoxamine base(486-16-8)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
毒性情報
HepatotoxicityLike many first generation antihistamines, carbinoxamine has not been linked to liver test abnormalities or to clinically apparent liver injury. The reason for its hepatic safety may relate to low daily dose and limited duration of use.
Toxicity Summary
Carbinoxamine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Carbinoxamine's anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)
carbinoxamine
Clistin®
Antihistamines
Not Applicable
no-DILI-concern
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
化学と産業
薬理情報
ATC Code
R - Respiratory system
QR - Respiratory system
Pharmacodynamics
Carbinoxamine is a first generation antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, carbinoxamine competes with free histamine for binding at HA-receptor sites. Carbinoxamine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of carbinoxamine.
Mechanism of Action
Carbinoxamine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Carbinoxamine's anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
Biological Half-Life10 to 20 hours
Metabolism/MetabolitesHalf Life: 10 to 20 hours
FDA Pharmacological Classification
982A7M02H5
CARBINOXAMINE
Mechanisms of Action [MoA] - Histamine H1 Receptor Antagonists
Established Pharmacologic Class [EPC] - Histamine-1 Receptor Antagonist
Carbinoxamine is a Histamine-1 Receptor Antagonist. The mechanism of action of carbinoxamine is as a Histamine H1 Receptor Antagonist.
MeSH Pharmacological Classification
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