Levamisole

Base Information

• Chemical Name: Levamisole
• CAS No.: 14769-73-4
• Deprecated CAS: 53096-13-2
• Molecular Formula: C11H12N2S
• Molecular Weight: 204.296
• Hs Code.: 2934999090
• European Community (EC) Number: 238-836-5
• UNII: 2880D3468G
• DSSTox Substance ID: DTXSID4023206
• Nikkaji Number: J8.518I
• Wikipedia: Levamisole
• Wikidata: Q417097
• NCI Thesaurus Code: C61609
• RXCUI: 6371
• Metabolomics Workbench ID: 43130
• ChEMBL ID: CHEMBL1454
• Mol file: 14769-73-4.mol

Synonyms:Decaris;Dekaris;Hydrochloride, Levamisole;L-Tetramisole;Levamisole;Levamisole Hydrochloride;Levotetramisole;Solaskil

Chemical Property of Levamisole

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 6.61E-05mmHg at 25°C
• Melting Point: 230 - 233ºC
• Boiling Point: 344.382 °C at 760 mmHg
• PKA: 10.00±0.40(Predicted)
• Flash Point: 162.076 °C
• PSA: 40.90000
• Density: 1.326 g/cm³
• LogP: 1.51960
• Storage Temp.: 0-6°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 204.07211956
• Heavy Atom Count: 14
• Complexity: 246

Purity/Quality:

≥99% ^*data from raw suppliers

Levamisole 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CSC2=NC(CN21)C3=CC=CC=C3
• Isomeric SMILES: C1CSC2=N[C@H](CN21)C3=CC=CC=C3
• Recent ClinicalTrials: The Efficacy and Safety of Prednisone Combined With Huaiqihuang Granule for Primary Nephrotic Syndrome in Children
• Indications: Monoinfections with Ascaris lumbricoides. In polyinfections, mebendazole is the drug of choice. Levamisole (Ergamisol) is an antiparasitic drug that has been found to enhance T-cell function and cellular immunity. The drug improves survival of patients with resected colorectal cancers when combined with 5-fluorouracil; the mechanism of this interaction is not known. Levamisole does not have antitumor activity against established or metastatic cancer and has not been found useful in the adjuvant therapy of cancers other than colorectal cancer. The major adverse effects of levamisole are nausea and anorexia. Skin rashes, itching, flulike symptoms, and fevers also have been observed. Levamisole (Ergamisol) was originally developed as an antihelminthic drug. It potentiates the stimulatory effects of antigens, mitogens, lymphokines, and chemotactic factors on lymphocytes, granulocytes, and macrophages. It has been shown to increase T cell–mediated immunity. Levamisole has been used successfully in treating chronic infections. It also has been approved for use in combination with fluorouracil in the treatment of colorectal cancer.
• Uses: Biological response modifier. Levamisole is used for initial and secondary immunodeficient conditions, autoimmune diseases, chronic and reoccurring infections, large intestine adenocarcinoma, helmintosis, and rheumatoid arthritis. Synonyms of this drug are decaris, tetramizole, and others.Levimasole is also a drug of choice for ascardiasis. Numerous investigations show that a single dose of levamisole heals from 90 to 100% of patients with ascardiasis, in particular those infected with A. duodenale. It is less effective against ancylostomiasis and strongyloidiasis. However, it is not effective against N. americanus. It seems likely that it has a gangliostimulating effect on parasite tissues in both the parasympathetic and sympathetic regions. Moreover, it is presumed that this drug has an immunomodulatory effect on the host organism. Synonyms of this drug are decaris, solacil, ergamisol, tramisol, immunol, and others.
• Therapeutic Function: Antiinflammatory
• Clinical Use: Ascariasis Hookworm infection Levamisole has been used in rheumatoid arthritis and some other conditions that are said to respond to its immunomodulatory activity.

Technology Process of Levamisole

There total 17 articles about Levamisole 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: 98.32%

levamisole hydrochloride (16595-80-5,74191-78-9) → Levamisole (14769-73-4)

Guidance literature:

With sodium hydroxide; In diethyl ether; water; Inert atmosphere;

DOI:10.1021/ol2012617

Reference yield: 65.0%

carbon disulfide (75-15-0,12122-00-8) + (1S)-1-phenylethylene-1,2-diamine (62779-70-8) + ethylene dibromide (106-93-4) → Levamisole (14769-73-4)

Guidance literature:

carbon disulfide; (1S)-1-phenylethylene-1,2-diamine; In ethanol; water;

ethylene dibromide; With sodium carbonate; In ethanol; water;

DOI:10.1016/j.molcata.2015.08.009

Reference yield: 60.0%

(S)-4-Phenyl-4,5-dihydro-1H-imidazole-2-thiol (16595-77-0) + ethylene dibromide (106-93-4) → Levamisole (14769-73-4)

Guidance literature:

With sodium carbonate; In isopropyl alcohol;

DOI:10.1002/anie.201103077

upstream raw materials:

(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine hydrochloride

Tetramisole

(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine

(S)-2-Amino-1-phenyl-1-ethanol

Downstream raw materials:

(6S,11aΞ)-1,3-di-naphthalen-1-yl-6-phenyl-tetrahydro-thiazolo[2',3':2,3]imidazo[1,2-a][1,3,5]triazine-2,4-dione

levamisole citrate

levamisole L-ascorbate

levamisole hydrochloride

Refernces

• 1、 Szeleczky, Zsolt,Kis-Mihály, Erzsébet,Semsey, Sándor,Pataki, Hajnalka,Bagi, Péter,Pálovics, Emese,Marosi, Gy?rgy,Pokol, Gy?rgy,Fogassy, Elemér,Madarász, János. "Effect of ultrasound-assisted crystallization in the diastereomeric salt resolution of tetramisole enantiomers in ternary system with O,O′-dibenzoyl-(2R,3R)-tartaric acid". . p. 8 - 17. Retrieved 2016.
• 2、 Schuppe, Alexander W.,Huang, David,Chen, Yifeng,Newhouse, Timothy R.. "Total Synthesis of (-)-Xylogranatopyridine B via a Palladium-Catalyzed Oxidative Stannylation of Enones". supporting information. p. 2062 - 2066. Retrieved 2018/02/19.
• 3、 Feng, Xiaoling,Yang, Yi,Wang, Jianhua. "Preparation and immunological evaluation of organic acid salts of levamisole". . p. 634 - 640. Retrieved 2014/06/09.