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147780-50-5 分子结构
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10-{1-azabicyclo[2.2.2]octan-3-ylmethyl}-10H-phenothiazine

ChemBase编号:942
分子式:C20H22N2S
平均质量:322.46708
单一同位素质量:322.15036971
SMILES和InChIs

SMILES:
S1c2c(N(CC3C4CCN(C3)CC4)c3c1cccc3)cccc2
Canonical SMILES:
c1ccc2c(c1)N(CC1CN3CCC1CC3)c1c(S2)cccc1
InChI:
InChI=1S/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2
InChIKey:
HOKDBMAJZXIPGC-UHFFFAOYSA-N

引用这个纪录

CBID:942 http://www.chembase.cn/molecule-942.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
10-{1-azabicyclo[2.2.2]octan-3-ylmethyl}-10H-phenothiazine
IUPAC传统名
quitadrill
mequitazine
10-{1-azabicyclo[2.2.2]octan-3-ylmethyl}-10H-phenothiazine
商标名
Butix
Instotal
Kitazemin
Metaplexan
Mircol
Primalan
Vigigan
Virginan
Zesulan
别名
Mequitazina [INN-Spanish]
Mequitazina [Spanish]
Mequitazinum [INN-Latin]
Mequitazine
10-(1-Azabicyclo[2.2.2]oct-3-ylmethyl)-10H-phenothiazine
10-(3-Quinuclidinylmethyl)phenothiazine
Butix
LM 209
Metaplexan
Mircol
NSC 303612
Nipolazin
Primalan
Quitadrill
Zesulan
(R)-10-(1-Azabicyclo[2.2.2]oct-3-ylmethyl)-10H-phenothiazine
(+)-Mequitazine
(R)-(+)-Mequitazine
Instotal
Kitazemin
Mequitazinum
Vigigan
Virginan
Mequitazine
CAS号
147780-50-5
29216-28-2
PubChem SID
46505779
160964405
PubChem CID
4066

数据来源

数据来源

所有数据来源 商品来源 非商品来源

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) 1.2331452  LogD (pH = 7.4) 2.961917 
Log P 4.1948013  摩尔折射率 99.0543 cm3
极化性 38.213127 Å3 极化表面积 6.48 Å2
可自由旋转的化学键 里宾斯基五规则 true 
Log P 5.38  LOG S -4.91 
溶解度 4.01e-03 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
Chloroform expand 查看数据来源
Methanol expand 查看数据来源
外观
Crystalline Solid expand 查看数据来源
White Solid expand 查看数据来源
熔点
130-131°C expand 查看数据来源
143-145°C expand 查看数据来源
疏水性(logP)
4.7 expand 查看数据来源
保存条件
Refrigerator expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
生物活性机理
Mequitazine binds to the histamine H1 receptor sites on effector cells in the gastrointestinal tract, blood vessels, and respiratory tract. expand 查看数据来源
This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
应用领域
Antiallergic agent expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank TRC TRC
DrugBank -  DB01071 external link
Item Information
Drug Groups approved
Description Mequitazine is a histamine H1 antagonist (antihistamine). It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
Indication For the treatment of Hay fever, urticaria (hives) and allergic rhinitis
Pharmacology In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Mequitazine is a histamine H1 antagonist. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
Affected Organisms
Humans and other mammals
References
Ramirez Chanona N, del Rio Navarro BE, Perez Martin J: [Efficacy of mequitazine (Primalan) on the relief of symptoms of allergic rhinoconjunctivitis in children. Documented clinical experience] Rev Alerg Mex. 2005 Nov-Dec;52(6):221-5. [Pubmed]
Theunissen EL, Vermeeren A, van Oers AC, van Maris I, Ramaekers JG: A dose-ranging study of the effects of mequitazine on actual driving, memory and psychomotor performance as compared to dexchlorpheniramine, cetirizine and placebo. Clin Exp Allergy. 2004 Feb;34(2):250-8. [Pubmed]
Nakamura K, Yokoi T, Kodama T, Inoue K, Nagashima K, Shimada N, Shimizu T, Kamataki T: Oxidation of histamine H1 antagonist mequitazine is catalyzed by cytochrome P450 2D6 in human liver microsomes. J Pharmacol Exp Ther. 1998 Feb;284(2):437-42. [Pubmed]
Persi L, Dupin O, Arnaud B, Trinquand C, Michel FB, Bousquet J: Efficacy of mequitazine in comparison with placebo assessed by ocular challenge with allergen in allergic conjunctivitis. Allergy. 1997 Apr;52(4):451-4. [Pubmed]
External Links
Wikipedia
Toronto Research Chemicals -  M225105 external link
R-Enantiomer of Mequitazine. It is an antihistamine.
Toronto Research Chemicals -  M225110 external link
It is an antihistamine.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Ramirez Chanona N, del Rio Navarro BE, Perez Martin J: [Efficacy of mequitazine (Primalan) on the relief of symptoms of allergic rhinoconjunctivitis in children. Documented clinical experience] Rev Alerg Mex. 2005 Nov-Dec;52(6):221-5. Pubmed
  • Theunissen EL, Vermeeren A, van Oers AC, van Maris I, Ramaekers JG: A dose-ranging study of the effects of mequitazine on actual driving, memory and psychomotor performance as compared to dexchlorpheniramine, cetirizine and placebo. Clin Exp Allergy. 2004 Feb;34(2):250-8. Pubmed
  • Nakamura K, Yokoi T, Kodama T, Inoue K, Nagashima K, Shimada N, Shimizu T, Kamataki T: Oxidation of histamine H1 antagonist mequitazine is catalyzed by cytochrome P450 2D6 in human liver microsomes. J Pharmacol Exp Ther. 1998 Feb;284(2):437-42. Pubmed
  • Persi L, Dupin O, Arnaud B, Trinquand C, Michel FB, Bousquet J: Efficacy of mequitazine in comparison with placebo assessed by ocular challenge with allergen in allergic conjunctivitis. Allergy. 1997 Apr;52(4):451-4. Pubmed
  • Uzan, A., et al.: Xenobiotica, 6, 633 (1976)
  • Persi, L., et al.: Alergy, 52, 451 (1976)
  • Nakamura, K., et al.: J. Pharmacol. Exp. Ther., 284, 437 (1976)
  • Theunissen, E., et al.: Clin. Exp. Allergy, 34, 250 (1976)
  • Uzan, A., et al.: Xenobiotica, 6, 633 (1976)
  • Persi, L., et al.: Alergy, 52, 451 (1976)
  • Nakamura, K., et al.: J. Pharmacol. Exp. Ther., 284, 437 (1976)
  • Theunissen, E., et al.: Clin. Exp. Allergy, 34, 250 (1976)
  • Ger. Pat., 1970, 2 009 555; CA, 73, 131017r, (synth)
  • Uzan, A. et al., Xenobiotica, 1976, 6, 633, (metab)
  • Uzan, A. et al., J. Pharm. Pharmacol., 1979, 31, 701, (pharmacol)
  • Ger. Pat., 1985, 3 509 460; CA, 104, 148890, (synth, Mequitazine)
  • Criscuolo, M. et al., Eur. J. Pharmacol., 1986, 126, 81, (pharmacol, Mequitazine)
  • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5665, (synonyms)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 942
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MCJ400
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