MedKoo Cat#: 100540 | Name: Levamisole hydrochloride
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Levamisole hydrochloride is the orally bioavailable hydrochloride salt of the synthetic imidazothiazole derivative levamisole with anthelminthic and immunostimulating activities. In immunosuppressed states, levamisole may restore immune function by: 1) stimulating antibody formation, 2) stimulating T-cell activation and proliferation, 3) potentiatiating monocyte and macrophage phagocytosis and chemotaxis and 4) increasing neutrophil mobility, adherence, and chemotaxis. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Chemical Structure

Levamisole hydrochloride
CAS#16595-80-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 100540

Name: Levamisole hydrochloride

CAS#: 16595-80-5 (HCl)

Chemical Formula: C11H12N2S

Exact Mass: 240.0488

Molecular Weight: 240.75

Elemental Analysis: C, 64.67; H, 5.92; N, 13.71; S, 15.70

Price and Availability

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10g USD 210.00
25g USD 360.00
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Related CAS #
14769-73-4 (free base) 16595-80-5 (HCl) 32093-35-9 (phosphate)
Synonym
ltetramisole hydrochloride; US brand name: Ergamisol. Foreign brand names: Ascaridil; Decaris; Ergamisole; Ketrax; Solaskil. Abbreviation: LEV. Code names: ICI59623; R 12564; RP20605.
IUPAC/Chemical Name
(S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride
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
SMILES Code
[H]Cl.C12=N[C@@H](C3=CC=CC=C3)CN1CCS2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
 According to http://en.wikipedia.org/wiki/Levamisole, Levamisole (marketed as the hydrochloride salt under the trade name Ergamisol) is an anthelminthic and immunomodulator belonging to a class of synthetic imidazothiazole derivatives. It was discovered at Janssen Pharmaceutica in 1966. Levamisole has been used in humans to treat parasitic worm infections, and has been studied in combination with other forms of chemotherapy for colon cancer, melanoma, and head and neck cancer. The drug was withdrawn from the U.S. and Canadian markets in 2000 and 2003 respectively, due to the risk of serious side effects and the availability of more effective replacement medications. Currently, levamisole remains in veterinary use as a dewormer for livestock. The medication has also been increasingly used as an adulterant in cocaine sold in the US and Canada, resulting in serious side effects.
Product Data
Biological target:
Levamisole ((-)-Tetramisole) hydrochloride is an anthelmintic and immunomodulator belonging to a class of synthetic imidazothiazole derivatives.
In vitro activity:
Levamisole displayed a significant suppressive effect on the in vitro adipogenic differentiation of AA BM-MSCs. Mechanistic investigation revealed that levamisole could increase the expression of ZFP36L1 which was subsequently demonstrated to function as a negative regulator of adipogenic differentiation of AA BM-MSCs through lentivirus-mediated ZFP36L1 knock-down and overexpression assay. Reference: J Cell Mol Med. 2018 Sep;22(9):4496-4506. https://pubmed.ncbi.nlm.nih.gov/29993187/
In vivo activity:
Acute toxicity and neurobehavioral effects of the veterinary anthelmintic tetramisole were examined in male albino mice. Subcutaneous injection of tetramisole at 0.5 and 1mg/kg did not significantly affect general locomotor activity of the mice in 5-min open-field activity test or negative geotaxis performance and landing foot splay. However, the 1mg/kg dose of tetramisole significantly increased the stereotyped behavior (grooming, sniffing, biting and licking and head bobbing) of the mice when compared to the control group. Reference: Neurotoxicology. 2006 Mar;27(2):153-7. https://pubmed.ncbi.nlm.nih.gov/16157386/
Solvent mg/mL mM comments
Solubility
DMSO 13.8 57.11
Ethanol 30.3 125.65
Water 49.0 203.53
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 240.75 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Liu LL, Liu L, Liu HH, Ren SS, Dou CY, Cheng PP, Wang CL, Wang LN, Chen XL, Zhang H, Chen MT. Levamisole suppresses adipogenesis of aplastic anaemia-derived bone marrow mesenchymal stem cells through ZFP36L1-PPARGC1B axis. J Cell Mol Med. 2018 Sep;22(9):4496-4506. doi: 10.1111/jcmm.13761. Epub 2018 Jul 11. PMID: 29993187; PMCID: PMC6111807. 2. Nageshwari B, Merugu R. Effect of levamisole on expression of CD138 and interleukin-6 in human multiple myeloma cell lines. Indian J Cancer. 2017 Jul-Sep;54(3):566-571. doi: 10.4103/ijc.IJC_349_17. PMID: 29798960. 3. Mohammad FK, Faris GA, Rhayma MS, Ahmed K. Neurobehavioral effects of tetramisole in mice. Neurotoxicology. 2006 Mar;27(2):153-7. doi: 10.1016/j.neuro.2005.08.003. Epub 2005 Sep 12. PMID: 16157386. 4. Błach-Olszewska Z, Zaczyńska E. Influence of L-tetramisole on the interferon production by mouse peritoneal and L929 cells. Arch Immunol Ther Exp (Warsz). 1991;39(5-6):597-604. PMID: 1841556.
In vitro protocol:
1. Liu LL, Liu L, Liu HH, Ren SS, Dou CY, Cheng PP, Wang CL, Wang LN, Chen XL, Zhang H, Chen MT. Levamisole suppresses adipogenesis of aplastic anaemia-derived bone marrow mesenchymal stem cells through ZFP36L1-PPARGC1B axis. J Cell Mol Med. 2018 Sep;22(9):4496-4506. doi: 10.1111/jcmm.13761. Epub 2018 Jul 11. PMID: 29993187; PMCID: PMC6111807. 2. Nageshwari B, Merugu R. Effect of levamisole on expression of CD138 and interleukin-6 in human multiple myeloma cell lines. Indian J Cancer. 2017 Jul-Sep;54(3):566-571. doi: 10.4103/ijc.IJC_349_17. PMID: 29798960.
In vivo protocol:
1. Mohammad FK, Faris GA, Rhayma MS, Ahmed K. Neurobehavioral effects of tetramisole in mice. Neurotoxicology. 2006 Mar;27(2):153-7. doi: 10.1016/j.neuro.2005.08.003. Epub 2005 Sep 12. PMID: 16157386. 2. Błach-Olszewska Z, Zaczyńska E. Influence of L-tetramisole on the interferon production by mouse peritoneal and L929 cells. Arch Immunol Ther Exp (Warsz). 1991;39(5-6):597-604. PMID: 1841556.