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Levamisole

Product Name:
Levamisole
CAS No.
14769-73-4
Chemical Name:
Levamisole
CBNumber:
CB3335709
Molecular Formula:
C11H12N2S
Formula Weight:
204.29
MOL File:
14769-73-4.mol
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Levamisole Property

Melting point:
60-61.5°
alpha 
D25 -85.1° (c = 10 in chloroform)
Boiling point:
344.4±45.0 °C(Predicted)
Density 
1.32±0.1 g/cm3(Predicted)
storage temp. 
0-6°C
pka
10.00±0.40(Predicted)
CAS DataBase Reference
14769-73-4(CAS DataBase Reference)
EPA Substance Registry System
Levamisole (14769-73-4)
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Levamisole Chemical Properties,Usage,Production

Pharmacology and mechanism of action

Levamisole is the L-isomer of tetramisole and is more active than the racemic mixture. It was introduced in 1966 as a veterinary drug and a little later as a human anthelminthic drug against ascariasis. The drug has also shown to be effective against hookworms (Ancylostoma duodenale and Necator americanus), but results of reported studies are inconsistent [1]. The mechanism of action of levamisole in helminthiasis is through its stimulation of autonomic ganglia (nicotinic receptors) of the worms. On exposure to the drug, immature and adult worms show spastic contraction followed by tonic paralysis. This mechanism seems to be common to other anthelminthics such as pyrantel and bephenium hydroxynaphthoate [2]. In higher doses, levamisole acts as an immunostimulant. It restores depressed cell-mediated immune mechanisms in peripheral T-lymphocytes, but may have marginal effects in immunologically competent individuals [3]. The clinical implication of this effect in the treatment of helminthiasis is unknown.

Indications

Monoinfections with Ascaris lumbricoides. In polyinfections, mebendazole is the drug of choice.

Side effects

During the treatment of nematode infections the drug produces minor side effects including nausea, vomiting, abdominal pain and headache [4, 5]. During prolonged treatment as an immunomodulator in rheumatic arthritis and in cancer patients, serious side effects such as blood disorders (agranulocytosis, neutropenia and thrombocytopenia), kidney damage, influenza-like reactions, vasculitis, photosensitivity and allergy to the drug have been reported [6, 7].

Contraindications and precautions

The drug should be avoided in patients allergic to the drug. Administration of levamisole may provoke a reaction similar to that seen after intake of alcohol together with disulfiram. During long-term treatment, patients with kidney damage or with blood disorders may experience exacerbation of their diseases.

Interactions

Levamisole has been reported to displace the protein binding of rifampicin in vitro [8]. The clinical significance of this is as yet unknown.

Preparations

Available as levamisole hydrochloride: 118 mg is equivalent to 100 mg base.
• Ketrax® (Zeneca). Oral solution 40 mg base per 5 ml. Tablets 40 mg base.
• Solaskil® (Rhône-Poulenc Rorer). Tablets 30 mg base, 150 mg base.
• Ergamisol® (Lederle). Tablets 50 mg base.
• Levamisol® (Janssen). Tablets 50 mg base.

References

1. Miller MJ (1980). Use of levamisole in parasitic infections. Drugs, 19, 122–130.
2. van Wauwe J, Janssen PAJ (1991). On the biochemical mode of action of levamisole: an update. Int J Immunopharmacol, 13, 3–9.
3. Renoux G (1980). The general immunopharmacology of levamisole. Drugs, 19, 89–99.
4. Lionel ND, Mirando EH, Nanayakkara JC, Soysa PE (1969). Levamisole in the treatment of ascariasis in children. BMJ, 4, 340–341.
5. Farid Z, Bassily S, Miner WF, Hassan A, Laughli LW (1977). Comparative single-dose treatment of hookworm and roundworm infections with levamisole, pyrantel and bephenium. J Trop Med Hyg, 80, 107–108.
6. Chrisp P, McTavish D (1991). Levamisole/fluorouracil: A review of their pharmacology and adjuvant therapeutic use in colorectal cancer. Drugs & Aging, 14, 317–337.
7. Amery WK, Butterworth BS (1983) The dosage regimen of levamisole in cancer: is it related to efficacy and safety Int J Immunopharmacol, 5, 1–9.
8. Pérez-Gallardo L, Blanco ML, Soria H, Escanero JF (1992). Displacement of rifampicin bound to serum proteins by addition of levamisole. Biomed Pharmacother, 46, 173–174.

Uses

Biological response modifier.

Definition

ChEBI: A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in huma s as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.

Indications

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.

Indications

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.

brand name

Ergamisol (Janssen).

Antimicrobial activity

Its principal activity is against Asc. lumbricoides and hookworms. Worms are paralyzed and passed out in the feces within a few hours.

Pharmaceutical Applications

The l-isomer of tetramisole, available as the monohydrochloride. The d-isomer has no anthelmintic activity. It is very soluble in water and is stable in the dry state.

Pharmacokinetics

Oral absorption: c. 90%
Cmax 150 mg oral: 0.5 mg/L after c. 2 h
Plasma half-life: c. 4 h
Volume of distribution: 100–120 L
Levamisole is rapidly absorbed from the gut and extensively metabolized in the liver. It is excreted chiefly in the urine.

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.

Side effects

Nausea, gastrointestinal upsets and very mild neurological problems have been reported.

Veterinary Drugs and Treatments

Depending on the product licensed, levamisole is indicated for the treatment of many nematodes in cattle, sheep and goats, swine, poultry. In sheep and cattle, levamisole has relatively good activity against abomasal nematodes, small intestinal nematodes (not particularly good against Strongyloides spp.), large intestinal nematodes (not Trichuris spp.), and lungworms. Adult forms of species that are usually covered by levamisole, include: Haemonchus spp., Trichostrongylus spp., Osteragia spp., Cooperia spp., Nematodirus spp., Bunostomum spp., Oesophagostomum spp., Chabertia spp., and Dictyocaulus vivapurus. Levamisole is less effective against the immature forms of these parasites, and is generally ineffective in cattle (but not sheep) against arrested larval forms. Resistance of parasites to levamisole is a growing concern.
In swine, levamisole is indicated for the treatment of Ascaris suum, Oesophagostomum spp., Strongyloides, Stephanurus, and Metastrongylus.
Levamisole has been used in dogs as a microfilaricide to treat Dirofilaria immitis infection in the past, but is rarely used today. It has also garnered some interest as an immunostimulant in the adjunctive therapy of various neoplasms.
Because of its narrow margin for safety and limited efficacy against many equine parasites, levamisole is not generally used in horses as an antiparasitic agent. It has been tried as an immune stimulant, however.

Levamisole Preparation Products And Raw materials Raw materials

Raw materials

Preparation Products

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Levamisole Suppliers

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Chengdu Saint - Kay Biotechnology Co., Ltd.
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Pharmacology and mechanism of action Indications Side effects Contraindications and precautions Interactions Preparations References