Niclosamide

Base Information

• Chemical Name: Niclosamide
• CAS No.: 50-65-7
• Molecular Formula: C13H8Cl2N2O4
• Molecular Weight: 327.124
• Hs Code.: 29242990
• European Community (EC) Number: 200-056-8,215-811-7
• NSC Number: 758440,178296
• UNII: 8KK8CQ2K8G
• DSSTox Substance ID: DTXSID7040362
• Nikkaji Number: J4.106H
• Wikipedia: Niclosamide
• Wikidata: Q418523
• NCI Thesaurus Code: C66240
• Pharos Ligand ID: PX7KWXZRUQNK
• Metabolomics Workbench ID: 43707
• ChEMBL ID: CHEMBL1448
• Mol file: 50-65-7.mol

Synonyms:Bayer 2353;Bayer 73;Bayluscide;Clonitralide;Fenasal;Niclocide;Niclosamide;Niclosamide, 2-Aminoethanol (1:1);Phenasal;Radewerm;Trédémine;Yomesan

Chemical Property of Niclosamide

Chemical Property:

• Appearance/Colour: white to yellowish odourless crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 225-230oC
• Refractive Index: 1.709
• Boiling Point: 413.905 °C at 760 mmHg
• PKA: 7.45±0.43(Predicted)
• Flash Point: 204.122 °C
• PSA: 95.15000
• Density: 1.616 g/cm³
• LogP: 4.45570
• Storage Temp.: 0-6°C
• Solubility.: acetone: methanol: soluble50mg/mL (methanol:acetone (1:1))
• Water Solubility.: 13.32mg/L(25 oC)
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 325.9861121
• Heavy Atom Count: 21
• Complexity: 404

Purity/Quality:

99% ^*data from raw suppliers

Niclosamide ^*data from reagent suppliers

Safty Information:

• Statements: 50
• Safety Statements: 29

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])Cl)NC(=O)C2=C(C=CC(=C2)Cl)O
• Recent ClinicalTrials: Abiraterone Acetate, Niclosamide, and Prednisone in Treating Patients With Hormone-Resistant Prostate Cancer
• Recent EU Clinical Trials: A RANDOMIZED PLACEBO-CONTROLLED PHASE 2 STUDY TO ASSESS THE SAFETY AND EFFICACY OF UNI91103 INTRANASAL ADMINISTRATION IN ADULTS WITH ASYMPTOMATIC OR MILDLY SYMPTOMATIC COVID-19
• Indications: Infections caused by T. saginata, D. latum, and H. nana. The drug is also effective against T. solium, but the danger of cysticercosis makes praziquantel preferable.
• Description: Niclosamide (50-65-7) reversibly inhibits mTORC1 signaling and stimulates autophagy.1 Inhibits activation and nuclear translocation of STAT3 selectively over STAT1 and STAT5. Niclosamide inhibits transcription of STAT3 target genes and induces cell cycle arrest and apoptosis in cells with constitutively active STAT3.2
• Uses: 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 transcription and DNA binding of the NF-?B pathway and it increases ROS levels to induce apoptosis in acute myelogenous leukemia (AML) cells. Niclosamide has been used extensively in the treatment of tapeworm infections caused by Taenia saginata, Taenia solium, Diphyllobothrium latum, Fasciolopsis buski, and Hymenolepis nana. It is an effective alternative to praziquantel for treating infections caused by T. saginata (beef tapeworm), T. solium (pork tapeworm), and D. latum (fish tapeworm) and is active against most other tapeworm infections. It is absorbed by intestinal cestodes but not nematodes.A single dose is usually adequate to produce a cure rate of 95%.With H. nana (dwarf tapeworm), a longer treatment course (up to 7 days) is necessary. Niclosamide is administered orally after the patient has fasted overnight and may be followed in 2 hours by purging (magnesium sulfate 15–30 g) to encourage complete expulsion of the cestode, especially T. solium, although this is not always considered necessary. Cure is assessed by follow-up stool examination in 3 to 5 months.With the availability of other agents, niclosamide is no longer widely used.The most widely employed agents are praziquantel and the benzimidazoles. An inhibitor of the Stat3 signaling pathway and also a FRAP inhibitor.
• Therapeutic Function: Anthelmintic
• Clinical Use: 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamideor 2,5 -dichloro-4 -nitrosalicylanilide (Cestocide, Mansonil,Yomesan) occurs as a yellowish white, water-insolublepowder. It is a potent taeniacide that causes rapid disintegrationof worm segments and the scolex. Penetration of thedrug into various cestodes appears to be facilitated by thedigestive juices of the host, in that very little of the drug isabsorbed by the worms in vitro. Niclosamide is well toleratedfollowing oral administration, and little or no systemicabsorption of it occurs. A saline purge 1 to 2 hours after ingestion of the taeniacide is recommended to remove thedamaged scolex and worm segments. This procedure ismandatory in the treatment of pork tapeworm infestation toprevent possible cysticercosis resulting from release of liveova from worm segments damaged by the drug. Niclosamide has been used extensively in the treatment of tapeworm infections caused by Taenia saginata, Taenia solium, Diphyllobothrium latum, Fasciolopsis buski, and Hymenolepis nana. It is an effective alternative to praziquantel for treating infections caused by T. saginata (beef tapeworm), T. solium (pork tapeworm), and D. latum (fish tapeworm) and is active against most other tapeworm infections. It is absorbed by intestinal cestodes but not nematodes.A single dose is usually adequate to produce a cure rate of 95%.With H. nana (dwarf tapeworm), a longer treatment course (up to 7 days) is necessary. Niclosamide is administered orally after the patient has fasted overnight and may be followed in 2 hours by purging (magnesium sulfate 15–30 g) to encourage complete expulsion of the cestode, especially T. solium, although this is not always considered necessary. Cure is assessed by follow-up stool examination in 3 to 5 months.With the availability of other agents, niclosamide is no longer widely used.The most widely employed agents are praziquantel and the benzimidazoles.

Technology Process of Niclosamide

There total 6 articles about Niclosamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

→ Niclosamide (50-65-7)

Guidance literature:

With phosphorus trichloride; In toluene; for 5h; Reflux;

Reference yield: 68.7%

5-chloro-2-hydroxybenzoic acid (321-14-2) + 2-Chloro-4-nitroaniline (121-87-9) → Niclosamide (50-65-7)

Guidance literature:

With phosphorus trichloride; In chlorobenzene; at 135 ℃; for 3h; Concentration; Solvent;

Reference yield: 48.0%

5-chloro-N-(2-chlorophenyl)-2-hydroxybenzamide (6626-92-2) → Niclosamide (50-65-7)

Guidance literature:

With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide; at 20 ℃; for 5h; Ionic liquid;

DOI:10.1016/j.tetlet.2019.151529

upstream raw materials:

5-chloro-2-hydroxybenzoic acid

2-Chloro-4-nitroaniline

5-chloro-2-hydroxybenzoyl chloride

5-chloro-N-(2-chlorophenyl)-2-hydroxybenzamide

Downstream raw materials:

5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-3-(piperidinomethyl)benzamide

5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-3-(morpholinomethyl)benzamide

2-Chloro-4-nitroaniline

dodecan-1-aminium 4-chloro-2-[(2-chloro-4-nitrophenyl)carbamoyl]phenoxide

Refernces

• 1、 Shamim, Khalida,Xu, Miao,Hu, Xin,Lee, Emily M,Lu, Xiao,Huang, Ruili,Shah, Pranav,Xu, Xin,Chen, Catherine Z.,Shen, Min,Guo, Hui,Chen, Lu,Itkin, Zina,Eastman, Richard T.,Shinn, Paul,Klumpp-Thomas, Carleen,Michael, Sam,Simeonov, Anton,Lo, Donald C.,Ming, Guo-li,Song, Hongjun,Tang, Hengli,Zheng, Wei,Huang, Wenwei. "Application of niclosamide and analogs as small molecule inhibitors of Zika virus and SARS-CoV-2 infection". supporting information. . Retrieved 2021/03/30.
• 2、 Zhang, Yanmei,Wang, Yican,Guo, Yiping,Liao, Jinxi,Tu, Zhengchao,Lu, Yongzhi,Ding, Ke,Tortorella, Micky D.,He, Jufang. "Identification and synthesis of low-molecular weight cholecystokinin B receptor (CCKBR) agonists as mediators of long-term synaptic potentiation". . p. 387 - 393. Retrieved 2019/02/01.