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86-42-0 分子结构
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4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol

ChemBase编号:495
分子式:C20H22ClN3O
平均质量:355.86118
单一同位素质量:355.14514002
SMILES和InChIs

SMILES:
Clc1cc2nccc(Nc3cc(CN(CC)CC)c(O)cc3)c2cc1
Canonical SMILES:
CCN(Cc1cc(ccc1O)Nc1ccnc2c1ccc(c2)Cl)CC
InChI:
InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)
InChIKey:
OVCDSSHSILBFBN-UHFFFAOYSA-N

引用这个纪录

CBID:495 http://www.chembase.cn/molecule-495.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
4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
IUPAC传统名
amodiaquine
4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
商标名
Basoquin
CAM-AQ1
CAM-AQI
Camochin
Camoquin
Camoquin HCL
Camoquinal
Camoquine
Flavoquin
Flavoquine
Miaquin
别名
Amodiaquin
Amodiaquine USP24
Amodiaquine, ring-closed
Amodiaquine Hydrochloride
Amodiaquine
4-[(7-Chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]phenol
4-[(7-Chloro-4-quinolyl)amino]-α-(diethylamino)-o-cresol
Camochin
Camoquin
Camoquinal
Camoquine
Flavoquine
Miaquin
NSC 13453
SN-10751
Amodiaquine
CAS号
86-42-0
PubChem SID
46506940
160963958
PubChem CID
2165
CHEBI ID
2674
ATC码
P01BA06
CHEMBL
682
Chemspider ID
2080
DrugBank ID
DB00613
KEGG ID
D02922
美国药典/FDA物质标识码
220236ED28
维基百科标题
Amodiaquine

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
Acid pKa 9.124549  质子受体
质子供体 LogD (pH = 5.5) 0.25545564 
LogD (pH = 7.4) 2.2423055  Log P 3.7630057 
摩尔折射率 103.2911 cm3 极化性 40.890427 Å3
极化表面积 48.39 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 4.83  LOG S -4.61 
溶解度 8.80e-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
DMSO expand 查看数据来源
Ethanol expand 查看数据来源
Methanol expand 查看数据来源
外观
Off-White to Pale Yellow Solid expand 查看数据来源
熔点
>208°C (dec.) expand 查看数据来源
疏水性(logP)
3.7 expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
半衰期
5.2 ± 1.7 (range 0.4 to 5.5) minutes expand 查看数据来源
生物活性机理
acts on the erythrocytic stages of the parasite expand 查看数据来源
Rapidly-acting blood schizonticide expand 查看数据来源
Some gametocytocidal activity 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
Antimalarial drug expand 查看数据来源
Protozoacide expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank -  DB00613 external link
Item Information
Drug Groups approved
Description A 4-aminoquinoquinoline compound with anti-inflammatory properties. [PubChem]
Indication For treatment of acute malarial attacks in non-immune subjects.
Pharmacology Amodiaquine, a 4-aminoquinoline similar to chloroquine in structure and activity, has been used as both an antimalarial and an anti-inflammatory agent for more than 40 years. Amodiaquine is at least as effective as chloroquine, and is effective against some chloroquine-resistant strains, although resistance to amodiaquine has been reported. The mode of action of amodiaquine has not yet been determined. 4-Aminoquinolines depress cardiac muscle, impair cardiac conductivity, and produce vasodilatation with resultant hypotension. They depress respiration and cause diplopia, dizziness and nausea.
Toxicity LD50 (mouse, intraperitoneal) 225 mg/kg, LD50 (mouse, oral) 550 mg/kg. Symptoms of overdose include headache, drowsiness, visual disturbances, vomiting, hypokalaemia, cardiovascular collapse and cardiac and respiratory arrest. Hypotension, if not treated, may progress rapidly to shock. Electrocardiograms (ECG) may reveal atrial standstill, nodal rhythm, prolonged intraventricular conduction time, broadening of the QRS complex, and progressive bradycardia leading to ventricular fibrillation and/or arrest.
Affected Organisms
Plasmodium
Biotransformation Hepatic biotransformation to desethylamodiaquine (the principal biologically active metabolite) is the predominant route of amodiaquine clearance with such a considerable first pass effect that very little orally administered amodiaquine escapes untransformed into the systemic circulation.
Absorption Rapidly absorbed following oral administration.
Half Life 5.2 ± 1.7 (range 0.4 to 5.5) minutes
References
Jewell H, Maggs JL, Harrison AC, O'Neill PM, Ruscoe JE, Park BK: Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica. 1995 Feb;25(2):199-217. [Pubmed]
Harrison AC, Kitteringham NR, Clarke JB, Park BK: The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem Pharmacol. 1992 Apr 1;43(7):1421-30. [Pubmed]
External Links
Wikipedia

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Jewell H, Maggs JL, Harrison AC, O'Neill PM, Ruscoe JE, Park BK: Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica. 1995 Feb;25(2):199-217. Pubmed
  • Harrison AC, Kitteringham NR, Clarke JB, Park BK: The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem Pharmacol. 1992 Apr 1;43(7):1421-30. Pubmed
  • Natarajan, L., et al.: Arzneim.-Forsch., 22, 1230 (1972)
  • Kracmer, J., et al.: Pharmazie, 29, 773 (1972)
  • Ahmad, I., et al.: Anal. Profiles Drug Subs., 21, 43 (1972)
  • Burckhalter, J.H. et al., J.A.C.S., 1948, 70, 1363, (synth)
  • Natarajan, P.N. et al., Arzneim.-Forsch., 1972, 22, 1230, (synth)
  • Kang, I.P.S. et al., J. Pharm. Pharmacol., 1974, 26, 201, (ir)
  • Barrow, A., Xenobiotica, 1974, 4, 669, (metab)
  • Winstanley, P.A. et al., Br. J. Clin. Pharmacol., 1990, 29, 479, (tox)
  • Ahmad, I. et al., Anal. Profiles Drug Subst., 1992, 21, 43, (rev)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 395
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专利

专利

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