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

• ChemBase编号: 4480
• 分子式: C13H8Cl2N2O4
• 平均质量: 327.11962
• 单一同位素质量: 325.98611211
• SMILES: c1cc(c(cc1[N+](=O)[O-])Cl)NC(=O)c1c(ccc(c1)Cl)O
• Canonical SMILES: Clc1ccc(c(c1)C(=O)Nc1ccc(cc1Cl)[N+](=O)[O-])O
• 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

名称和登记号

名称

• IUPAC标准名: 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
• IUPAC传统名: niclosamide
• 商标名: Niclocide
• 别名: 2′,5-二氯-4′-硝基水杨酸酰替苯胺; 氯硝柳胺; 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide; Niclosamide; 2′,5-Dichloro-4′-nitrosalicylanilide; Niclosamide; 2',5-Dichloro-4-nitrosalicylanilide; Niclosamide (Niclocide)

登记号

• CAS号: 50-65-7
• EC号: 200-056-8
• MDL号: MFCD00057597
• Beilstein号: 2820605
• PubChem SID: 160967912; 24278585; 99443295
• PubChem CID: 4477
• ATC码: P02DA01; QP52AG03
• CHEMBL: 1448
• Chemspider ID: 4322
• DrugBank ID: DB06803
• KEGG ID: D00436
• 美国药典/FDA物质标识码: 8KK8CQ2K8G
• 维基百科标题: Niclosamide

理论计算性质

JChem

• Acid pKa: 6.8910413
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 3.8924754
• LogD (pH = 7.4): 3.2942405
• Log P: 3.909639
• 摩尔折射率: 79.5025 cm^3
• 极化性: 29.329649 Å^3
• 极化表面积: 92.47 Å^2
• 可自由旋转的化学键: 3
• 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

分子性质

理化性质

• 熔点: 225-230 °C
• 蒸汽压: Very low at room temp
• 疏水性(logP): 4.345

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: VN8400000
• 联合国危险货物编号: 3077
• 德国WGK号: 2
• 联合国危险货物等级: 9
• 联合国危险货物包装类别(PG): 3
• GHS危险品标识: GHS09
• GHS警示词: Warning
• GHS危险声明: H400
• GHS警示性声明: P273
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 3077 9/PG 3

药理学性质

• 作用靶点: STAT

产品相关信息

• 纯度: 95%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C13H8Cl2N2O4

详细说明

MP Biomedicals - 02155827

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

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.

参考文献

• 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.
• 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.