Levamisole Hydrochloride

Base Information

• Chemical Name: Levamisole Hydrochloride
• CAS No.: 16595-80-5
• Deprecated CAS: 39170-95-1,74191-78-9,24593-45-1
• Molecular Formula: C11H12N2S^.HCl
• Molecular Weight: 240.757
• Hs Code.: 29349990
• European Community (EC) Number: 240-654-6
• NSC Number: 177023
• UNII: DL9055K809
• DSSTox Substance ID: DTXSID7047518
• Wikidata: Q27107205
• NCI Thesaurus Code: C610
• RXCUI: 227227
• ChEMBL ID: CHEMBL1770
• Mol file: 16595-80-5.mol

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

Chemical Property of Levamisole Hydrochloride

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Melting Point: 266-267 ºC
• Refractive Index: -126 ° (C=1, H2O)
• Boiling Point: 344.4 ºC at 760 mmHg
• Flash Point: 162.1 ºC
• PSA: 40.90000
• LogP: 2.32160
• Storage Temp.: 0-6°C
• Solubility.: Freely soluble in water, soluble in ethanol (96 per cent), slightly soluble in methylene chloride.
• Water Solubility.: 210 g/L (20 ºC)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 240.0487973
• Heavy Atom Count: 15
• Complexity: 246

Purity/Quality:

98% ^*data from raw suppliers

Levamisole Hydrochloride >99.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn
• Hazard Codes: T,Xn,F
• Statements: 25-20/21/22-39/23/24/25-23/24/25-11
• Safety Statements: 36/37/39-45-28A-36-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CSC2=NC(CN21)C3=CC=CC=C3.Cl
• Isomeric SMILES: C1CSC2=N[C@H](CN21)C3=CC=CC=C3.Cl
• Recent ClinicalTrials: Efficiency of Levamisole for Maintaining Remission After the First Flare of Steroid Sensitive Nephrotic Syndrome in Children
• Recent EU Clinical Trials: Prevention of relapse with Levamisole as adjuvant therapy to corticosteroids in children with first episode of idiopathic nephrotic syndrome
• Chemical Structure: Levamisole hydrochloride is the hydrochloride salt of levamisole, which is the levo-isomer of tetramisole. ^[1]
• Uses: Levamisole hydrochloride is a highly soluble anthelmintic drug to treat roundworms, hookworms, pinworms, and other parasitic infections. With potential applicability for BCS-based biowaivers in solid oral dosage forms. It's efficacy in treating parasitic worm infections and its inclusion on the WHO List of Essential Medicines. ^[1]; Also exhibits immunomodulatory activities, stimulating antibody formation and various immune functions. It's interaction with proteins such as beta-lactoglobulin has significant implications for food safety and health. ^[2]; Often formulated in compound suspensions with other anthelmintics for veterinary use. ^[4]
• Pharmacokinetics: Oral bioavailability in humans is approximately 65%.^[1]; Pharmacokinetic parameters measured in a study involving sheep. Main parameters include maximum plasma concentrations (C max), time to maximum concentration (T max), area under the time curve concentration (AUC last), and terminal half-life (T 1/2). Relative bioavailability of levamisole hydrochloride compound suspension in sheep plasma found to be 104.62%.^[4]
• History and Development: Discovered by Janssen Pharmaceutica in 1966. Belongs to the class of synthetic imidazothiazole derivatives. ^[1]; Originally used in human medicine but now primarily used in veterinary medicine. ^[3]
• Analysis Method: Various analytical methods have been developed for its determination in dosage forms, including nonaqueous titration and high-performance liquid chromatography (HPLC).^[3]
• References: [1] Biowaiver Monograph for Immediate-Release Dosage Forms: Levamisole Hydrochloride (DOI 10.1016/j.xphs.2022.12.014); [2] Change in thermal stability and molecular structure characteristics of whey protein beta-lactoglobulin upon the interaction with levamisole hydrochloride (DOI 10.1016/j.foodchem.2023.137073); [3] Stability-Indicating High-Performance Liquid Chromatographic Determination of Levamisole Hydrochloride in Bulk and Dosage Forms (DOI 10.1155/2020/6137897); [4] Pharmacokinetics study of oxyclozanide and levamisole hydrochloride compound suspension in sheep by LC-MS/MS (DOI 10.21203/rs.3.rs-2823340/v1)

Technology Process of Levamisole Hydrochloride

There total 4 articles about Levamisole Hydrochloride 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: 94.2%

levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) + toluene (108-88-3,15644-74-3,16713-13-6) → levamisole hydrochloride (16595-80-5,74191-78-9)

Guidance literature:

With sodium hydroxide; In water;

Reference yield: 92.1%

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

Guidance literature:

Levamisole; With sodium metabisulfite; pyrographite; In isopropyl alcohol; for 0.5h;

With hydrogenchloride; pH=4 - 5; Time;

Reference yield:

Tetramisole (5036-02-2) → levamisole hydrochloride (16595-80-5,74191-78-9) + (+)-Tetramisole hydrochloride (16595-76-9,74191-78-9)

Guidance literature:

With hydrogenchloride; In isopropyl alcohol; toluene; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(01)96641-4

upstream raw materials:

Tetramisole

toluene

Levamisole

Downstream raw materials:

levamisole citrate

levamisole L-ascorbate

Levamisole

C₂₂H₂₄N₆O₄S₂

Refernces

• 1、 -. "Pesticidal compositions in paste form". . . Retrieved 2008/06/13.
• 2、 -. "Process for isolating levamisole from tetramisole". . . Retrieved 2008/06/13.