CAS 50-65-7|Niclosamide|niclosamide|5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide|Niclocide|2',5-Dichloro-4-nitrosalicylanilide|Niclosamide (Niclocide)|Niclosamide|氯硝柳胺|2′,5-二氯-4′-硝...

基本信息

化学结构

分子式

C₁₃H₈Cl₂N₂O₄

分子量

327.11962

精确质量

325.98611211

电荷

InChI

InChI=1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19)

InChIKey

RJMUSRYZPJIFPJ-UHFFFAOYSA-N

Canonic Smiles

Clc1ccc(c(c1)C(=O)Nc1ccc(cc1Cl)[N+](=O)[O-])O

Isomeric Smiles

c1cc(c(cc1[N+](=O)[O-])Cl)NC(=O)c1c(ccc(c1)Cl)O

计算属性

JChem

Acid pKa

6.8910413

质子受体

质子供体

LogD (pH = 5.5)

3.8924754

LogD (pH = 7.4)

3.2942405

Log P

3.909639

摩尔折射率

79.5025

极化性

29.329649

极化表面积

92.47

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

4.49

LOG S

-4.61

溶解度

7.99e-03 g/l

数据来源

名称和标识

别名

Niclosamide2',5-Dichloro-4-nitrosalicylanilideNiclosamide (Niclocide)Niclosamide氯硝柳胺2′,5-二氯-4′-硝基水杨酸酰替苯胺2′,5-Dichloro-4′-nitrosalicylanilide5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

IUPAC传统名

niclosamide

IUPAC标准名

5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

商标名

Niclocide

名称和标识

数据登录号

PubChem CID

DrugBank ID

Chemspider ID

CAS号

KEGG ID

PubChem SID

9944329524278585160967912

维基百科标题

ATC码

美国药典/FDA物质标识码

CHEMBL

MDL号

EC号

Beilstein号

数据登录号

化合物性质

产品相关信息

下载链接

C13H8Cl2N2O4

95%

Free Base

理化性质

Very low at room temp

225-230 °C

4.345

药理学性质

STAT

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

MP Biomedicals

02155827

(2',5-Dichloro-4-nitrosalicylanilide)

Wikipedia

Niclosamide

DrugBank

DB06803

Drug Groups

approved

Description

Niclosamide is used for the treatment of most tapeworm infections. Helminths (worms) are multicellular organisms that infect very large numbers of humans and cause a broad range of diseases. Over 1 billion people are infected with intestinal nematodes, and many millions are infected with filarial nematodes, flukes, and tapeworms. They are an even greater problem in domestic animals.

Indication

For the treatment of tapeworm and intestinal fluke infections: Taenia saginata (Beef Tapeworm), Taenia solium (Pork Tapeworm), Diphyllobothrium latum (Fish Tapeworm), Fasciolopsis buski (large intestinal fluke). Niclosamide is also used as a molluscicide in the control of schistosomiasis.

Pharmacology

Niclosamide is an antihelminth used against tapeworm infections. It may act by the uncoupling of the electron transport chain to ATP synthase. The disturbance of this crucial metabolic pathway prevents creation of adenosine tri-phosphate (ATP), an essential molecule that supplies energy for metabolism.

Toxicity

Infrequent, mild, and transitory adverse events include nausea, vomiting, diarrhea, and abdominal discomfort.

Affected Organisms

Helminthic Microorganisms

Absorption

Niclosamide appears to be minimally absorbed from the gastrointestinal tract—neither the drug nor its metabolites have been recovered from the blood or urine.

References

• Rosenthal Philip J, "Chapter 53. Clinical Pharmacology of the Antihelminthic Drugs" (Chapter). Katzung BG: Basic & Clinical Pharmacology, 11e: "http://www.accessmedicine.com/content.aspx?aID=4516635":http://www.accessmedicine.com/content.aspx?aID=4516635.

• 2010. Detailed Drug Information for the Consumer?. Greenwood Village, CO. Thomson Reuters. ISBN-10: 1-56363-575-5. ISSN: 0740-4174. STAT!Ref Online Electronic Medical Library.

External Links

• [Wikipedia]

• [Drugs.com]

Sigma Aldrich

N3510

Application
Niclosamide is a teniacide in the anthelmintic family. It is effective against cestodes that infect humans. Niclosamide is used to study the Wnt/Frizzled-1 signaling pathway. It is used to inhibit the transcription and DNA binding of NF-κB in AML cells and ito induce apoptosis1.
Biochem/physiol Actions
Niclosamide is used to study the Wnt/Frizzled-1 signaling pathway. It inhibits mitochondrial oxidative phosphorylation of parasitic helminths.
Niclosamide uncouples oxidative phosphorylation in the tapeworm. It inhibits mitochondrial oxidative phosphorylation of parasitic helminths. It inhibits the NF-κB pathway in acute myelogenous leukemia (AML) cells. Niclosamide inhibits the transcription and DNA binding of NF-κB. It blocks tumor necrosis factor-induced IκBα phosphorylation, translocation of p65, and expression of NF-κB- regulated genes in AML cells. It increases ROS levels to induce apoptosis in AML cells1.

描述信息

参考文献

PubChem文献

数据源提供

• 2010. Detailed Drug Information for the Consumer?. Greenwood Village, CO. Thomson Reuters. ISBN-10: 1-56363-575-5. ISSN: 0740-4174. STAT!Ref Online Electronic Medical Library.

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

niclosamide

IUPAC标准名

5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

商标名

Niclocide

数据登录号

PubChem CID

DrugBank ID

Chemspider ID

CAS号

KEGG ID

PubChem SID

9944329524278585160967912

维基百科标题

ATC码

美国药典/FDA物质标识码

CHEMBL

MDL号

EC号

Beilstein号

描述信息

(2',5-Dichloro-4-nitrosalicylanilide)

Wikipedia

Niclosamide

DrugBank

DB06803

Drug Groups

approved

Description

Indication

Pharmacology

Toxicity

Infrequent, mild, and transitory adverse events include nausea, vomiting, diarrhea, and abdominal discomfort.

Affected Organisms

Helminthic Microorganisms

Absorption

Niclosamide appears to be minimally absorbed from the gastrointestinal tract—neither the drug nor its metabolites have been recovered from the blood or urine.

References

• 2010. Detailed Drug Information for the Consumer?. Greenwood Village, CO. Thomson Reuters. ISBN-10: 1-56363-575-5. ISSN: 0740-4174. STAT!Ref Online Electronic Medical Library.

External Links

• [Wikipedia]

• [Drugs.com]

Sigma Aldrich

N3510

参考文献

PubChem文献

数据源提供

• 2010. Detailed Drug Information for the Consumer?. Greenwood Village, CO. Thomson Reuters. ISBN-10: 1-56363-575-5. ISSN: 0740-4174. STAT!Ref Online Electronic Medical Library.

生物活性

PubChem BioAssay

化合物性质

产品相关信息

下载链接

C13H8Cl2N2O4

95%

Free Base

理化性质

Very low at room temp

225-230 °C

4.345

药理学性质

STAT

化合物信息

ID:4480