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

• ChemBase ID: 4480
• Molecular Formular: C13H8Cl2N2O4
• Molecular Mass: 327.11962
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
• IUPAC Traditional name: niclosamide
• Brand Name: Niclocide
• Synonyms: 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide; Niclosamide; 2′,5-Dichloro-4′-nitrosalicylanilide; Niclosamide; 2',5-Dichloro-4-nitrosalicylanilide; Niclosamide (Niclocide); 2′,5-二氯-4′-硝基水杨酸酰替苯胺; 氯硝柳胺

Database IDs

• CAS Number: 50-65-7
• EC Number: 200-056-8
• MDL Number: MFCD00057597
• Beilstein Number: 2820605
• PubChem SID: 160967912; 24278585; 99443295
• PubChem CID: 4477
• ATC CODE: QP52AG03; P02DA01
• CHEMBL: 1448
• Chemspider ID: 4322
• DrugBank ID: DB06803
• KEGG ID: D00436
• Unique Ingredient Identifier: 8KK8CQ2K8G
• Wikipedia Title: Niclosamide

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.8910413
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.8924754
• LogD (pH = 7.4): 3.2942405
• Log P: 3.909639
• Molar Refractivity: 79.5025 cm^3
• Polarizability: 29.329649 Å^3
• Polar Surface Area: 92.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.49
• LOG S: -4.61
• Solubility (Water): 7.99e-03 g/l

PROPERTIES

Physical Property

• Melting Point: 225-230 °C
• Vapor Pressure: Very low at room temp
• Hydrophobicity(logP): 4.345

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: VN8400000
• UN Number: 3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 3077 9/PG 3

Pharmacology Properties

• Target: STAT

Product Information

• Purity: 95%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C13H8Cl2N2O4

DETAILS

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.

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.
• 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.