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Levamisole hydrochloride

Cat No.:V11764 Purity: ≥98%
Levamisole ((-)-Tetramisole) HCl is an anthelmintic and immunomodulator.
Levamisole hydrochloride
Levamisole hydrochloride Chemical Structure CAS No.: 16595-80-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10g
Other Sizes

Other Forms of Levamisole hydrochloride:

  • Levamisole-d5 hydrochloride ((-)-Tetramisole-d5 (hydrochloride))
  • Levamisole
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Levamisole ((-)-Tetramisole) HCl is an anthelmintic and immunomodulator. Levamisole HCl has significant antiviral effects against the HSV virus.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Levamisole hydrochloride causes neutropenia and agranulocytosis by preventing the formation of white blood cells. Numerous difficulties have been observed in cocaine users due to the growing use of levamisole hydrochloride as an adulterant [1] [2]. Levamisole hydrochloride inhibits most isoforms of alkaline phosphatase, including destructive and placental isoforms, reversibly and non-competitively (e.g., human fetus, kidney, and spleen) [3]. Thus, in biomedical experiments involving detection signal amplification that disrupts phosphatases, like in situ hybridization or Western blotting methods, it is supplied along with substrate to lower background phosphatase activity. C is mounted using it. elegans onto imaging-ready glass slides.
Toxicity/Toxicokinetics
Effects During Pregnancy and Lactation
◉ Overview of Lactation Use
Levamisole has been discontinued for human use in the United States due to its potential to cause agranulocytosis, but it is still used as an anthelmintic in other countries. There is currently no publicly available information regarding its excretion in breast milk. Some information suggests that levamisole use may be acceptable for breastfeeding women. However, due to limited experience with levamisole use during lactation, alternative medications may be preferred, especially when breastfeeding newborns or premature infants. The World Health Organization recommends that pregnant women taking levamisole should not breastfeed.
◉ Effects on Breastfed Infants
In the Democratic Republic of Congo, a cohort study of 33 infants followed hospitalized mothers taking nifurolimus who breastfed (the extent of breastfeeding was not specified). Thirty mothers received the full course of nifurulimide orally at 15 mg/kg daily for 30 doses; all mothers also received intravenous efornithine at 400 mg/kg daily for 7 days, 14 times daily, for the treatment of human African trypanosomiasis (sleeping sickness). Six of the breastfeeding mothers also received levamisole. No serious adverse events were reported in any of the breastfed infants.
◉ Effects on lactation and breast milk
As of the revision date, no relevant published information was found.
References

[1]. Centers for Disease Control and Prevention (CDC). Agranulocytosis associated with cocaine use - four States, March 2008-November 2009.MMWR Morb Mortal Wkly Rep. 2009 Dec 18;58(49):1381-5.

[2]. Agranulocytosis after consumption of cocaine adulterated with levamisole. Ann Intern Med. 2009 Feb 17;150(4):287-9.

[3]. Van Belle H. Alkaline phosphatase. I. Kinetics and inhibition by levamisole of purified isoenzymes from humans. Clin Chem. 1976 Jul;22(7):972-6.

[4]. The treatment of herpetic reinfection with levamisole. Am J Ophthalmol. 1978 Aug;86(2):245-9.

Additional Infomation
Levamisole hydrochloride is an organic molecular entity. Levamisole hydrochloride is the hydrochloride salt of the synthetic imidazothiazole derivative levamisole, possessing anthelmintic and immunomodulatory activities. Under immunosuppressive conditions, levamisole can restore immune function through: 1) stimulating antibody production; 2) stimulating T cell activation and proliferation; 3) enhancing phagocytosis and chemotaxis of monocytes and macrophages; and 4) increasing the migration, adhesion, and chemotaxis of neutrophils. As an anthelmintic, it has been tested in experiments on rheumatic diseases, showing that it can restore immune responses by enhancing macrophage chemotaxis and T lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial for rheumatoid arthritis, although dermatitis, leukopenia, thrombocytopenia, and nausea and vomiting have been reported as side effects. (Quoted from Smith and Reynard, Pharmacology Textbook, 1991, pp. 435-436)
See also: Levamisole (containing the active ingredient); Doramectin; Levamisole Hydrochloride (ingredient)...See more...
Drug Indications
Treatment of glomerulonephritis and nephrotic syndrome
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H13CLN2S
Molecular Weight
240.7523
Exact Mass
240.048
CAS #
16595-80-5
Related CAS #
Levamisole-d5 hydrochloride;1246819-64-6;Levamisole;14769-73-4
PubChem CID
27944
Appearance
White to off-white solid powder
Boiling Point
344.4ºC at 760 mmHg
Melting Point
226-231ºC
Flash Point
162.1ºC
Index of Refraction
-126 ° (C=1, H2O)
LogP
2.321
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Heavy Atom Count
15
Complexity
246
Defined Atom Stereocenter Count
1
SMILES
C1CSC2=N[C@H](CN21)C3=CC=CC=C3.Cl
InChi Key
LAZPBGZRMVRFKY-HNCPQSOCSA-N
InChi Code
InChI=1S/C11H12N2S.ClH/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10;/h1-5,10H,6-8H2;1H/t10-;/m1./s1
Chemical Name
(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole;hydrochloride
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~50 mg/mL (~207.68 mM)
DMSO : ~15.5 mg/mL (~64.38 mM)
Ethanol : ~12.5 mg/mL (~51.92 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 1.25 mg/mL (5.19 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear EtOH stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 1.25 mg/mL (5.19 mM) (saturation unknown) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 1.25 mg/mL (5.19 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 100 mg/mL (415.37 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.1537 mL 20.7684 mL 41.5369 mL
5 mM 0.8307 mL 4.1537 mL 8.3074 mL
10 mM 0.4154 mL 2.0768 mL 4.1537 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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