{2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylamine

• ChemBase编号: 628
• 分子式: C16H19ClN2O
• 平均质量: 290.78786
• 单一同位素质量: 290.11859092
• SMILES: Clc1ccc(C(OCCN(C)C)c2ncccc2)cc1
• Canonical SMILES: CN(CCOC(c1ccccn1)c1ccc(cc1)Cl)C
• InChI: InChI=1S/C16H19ClN2O/c1-19(2)11-12-20-16(15-5-3-4-10-18-15)13-6-8-14(17)9-7-13/h3-10,16H,11-12H2,1-2H3
• InChIKey: OJFSXZCBGQGRNV-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: {2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylamine
• IUPAC传统名: carbinoxamine
• 商标名: Allergefon; Clistin; Rotoxamine; Twiston
• 别名: Carbinoxamine Maleate; Paracarbinoxamine; Paracarinoxamine; Carbinoxamine

登记号

• CAS号: 486-16-8
• PubChem SID: 160964091; 46506787
• PubChem CID: 2564

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 0.14102614
• LogD (pH = 7.4): 1.7942975
• Log P: 3.2719407
• 摩尔折射率: 82.1278 cm^3
• 极化性: 32.299973 Å^3
• 极化表面积: 25.36 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.03
• LOG S: -3.11
• 溶解度: 2.28e-01 g/l

分子性质

理化性质

• 疏水性(logP): 2.6

详细说明

DrugBank - DB00748

• Drug Groups: approved
• Description: Carbinoxamine is a first generation antihistamine that 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. The product label for carbinoxamine as an over the counter cough and cold medicine is being modified to state "do not use" in children under 4 years of age in order to prevent and reduce misuse, as many unapproved carbinoxamine-containing preparations contained inappropriate labeling, which promoted unapproved uses (including management of congestion, cough, the common cold, and the use in children under 2 years of age), which can potentially cause serious health risks.
• Indication: For symptomatic relief of seasonal and perennial allergic rhinitis and vasomotor rhinitis, as well as allergic conjunctivitis caused by foods and inhaled allergens. Also for the relief of allergic reactions to blood or plasma, and the symptomatic management of mild, uncomplicated allergic skin manifestations of urticaria and angioedema.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• Half Life: 10 to 20 hours
• References: BEALE HD, RAWLING FF, FIGLEY KD: Clistin maleate; a clinical appraisal of a new antihistaminic. J Allergy. 1954 Nov;25(6):521-4. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• BEALE HD, RAWLING FF, FIGLEY KD: Clistin maleate; a clinical appraisal of a new antihistaminic. J Allergy. 1954 Nov;25(6):521-4. Pubmed