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Levamisole

CAS No.
14769-73-4
Chemical Name:
Levamisole
Synonyms
LEVAMISOLE BASE;(S)-6-phenyl-2,3,5,6-tetrahydroiMidazo[2,1-b]thiazole;lepuron;levomysol;Ketrax;LEVAMISOLE;l-tetramisole;Levamisole Wickr;Levamisole powder;(S)-(-)-Levamisole
CBNumber:
CB3335709
Molecular Formula:
C11H12N2S
Molecular Weight:
204.29
MDL Number:
MFCD00066738
MOL File:
14769-73-4.mol
MSDS File:
SDS
Last updated:2024-01-19 18:04:22

Levamisole Properties

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. Sealed in dry,2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
form Solid
pka 10.00±0.40(Predicted)
color Off-White to Pale Yellow
InChI InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
InChIKey HLFSDGLLUJUHTE-SNVBAGLBSA-N
SMILES S1CCN2C[C@H](C3=CC=CC=C3)N=C12
CAS DataBase Reference 14769-73-4(CAS DataBase Reference)
FDA 21 CFR 556.350
NCI Dictionary of Cancer Terms levamisole
FDA UNII 2880D3468G
ATC code P02CE01
EPA Substance Registry System Levamisole (14769-73-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302+H312+H332-H315-H319-H335
Precautionary statements  P261-P264b-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362+P364-P403+P233-P501c

Levamisole price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
AK Scientific U487 Levamisole 14769-73-4 1g $98 2021-12-16 Buy
Activate Scientific AS47964 (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole 97% ee 14769-73-4 1g $108 2021-12-16 Buy
American Custom Chemicals Corporation API0009572 (S)-6-PHENYL-2,3,5,6-TETRAHYDROIMIDAZO[2,1-B][1,3]THIAZOLE 95.00% 14769-73-4 1G $255.15 2021-12-16 Buy
Activate Scientific AS47964 (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole 97% ee 14769-73-4 5G $331 2021-12-16 Buy
AK Scientific J52657 Levamisole 14769-73-4 25g $840 2021-12-16 Buy
Product number Packaging Price Buy
U487 1g $98 Buy
AS47964 1g $108 Buy
API0009572 1G $255.15 Buy
AS47964 5G $331 Buy
J52657 25g $840 Buy

Levamisole Chemical Properties,Uses,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.

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.

Originator

Solaskil,Specia,France,1971

Uses

Biological response modifier.

Uses

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.

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.

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.

Definition

ChEBI: Levamisole is 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 humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine. It has a role as an antinematodal drug, an antirheumatic drug, an immunomodulator, an immunological adjuvant and an EC 3.1.3.1 (alkaline phosphatase) inhibitor. It is an enantiomer of a dexamisole.

brand name

Ergamisol (Janssen).

Therapeutic Function

Antiinflammatory

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.

Mechanism of action

Levamisole has immunomodulating activity. It is believed that it regulates cellular mechanisms of the immune system, and the mechanism of its action may be associated with activation and proliferative growth of T-lymphocytes, increased numbers of monocytes and activation of macrophages, and also with increased activity and hemotaxis of neutrophylic granulocytes. Levamisole also exhibits anthelmint action. It also increases the body’s overall resistivity and restores altered T-lymphocyte and phagocyte function. It can also fulfill an immunomodulatory function by strengthening the weak reaction of cellular immunity, weakening strong reaction, and having no effect on normal reaction.

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.

Synthesis

Levamisole, 2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole (31.1.4), is synthesized in various ways. One of them begins with α-bromoacetophenone, the reaction of which with 2-imino-1,3-thiazolidine gives 3-phenacyl-2-imino-1,3-thiazolidine (31.1.1). Reacting this product with acetic anhydride gives 3-phenacyl-2-acetylimino-1,3- thiazolidine (31.1.2). The ketone group in the resulting compound is reduced to an alcohol using sodium borohydride, and the resulting hydroxyl group in (31.1.3) is replaced with chlorine using thionyl chloride. Heating the product in acetic anhydride, the imidazole cycle closes, forming the product (31.1.4).
Synthesis_14769-73-4_1
A somewhat different approach was realized when using styrene oxide as the initial starting material. Reacting it with 2-imino-1,3-thiazolidine gives 3-(2-phenyl-2-hydroxyethyl)- 2-imino-1,3-thiazolidine (31.1.5), which is subsequently treated with thionyl chloride and then acetic anhydride to give the desired levamisole (31.1.4).
Finally, the following scheme of making the product has been proposed using the same styrene oxide. Styrene oxide is reacted with aziridine, forming 2-aziridion-1- phenylethanol-1 (31.1.6). Treating this with potassium isothiocyanate or thiourea gives 3- (2-phenyl-2-hydroxyethyl)-2-amino-1,3-thiazolidine (31.1.5), and subsequent treatment with thionyl chloride (such as described above) and then with acetic anhydride gives the desired levamisole (31.1.4).
Synthesis_14769-73-4_2

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.

112790-85-9
14769-73-4
Synthesis of Levamisole from 112790-85-9

Levamisole Preparation Products And Raw materials

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View Lastest Price from Levamisole manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Levamisole pictures 2024-03-19 Levamisole
14769-73-4
US $10.00-5.00 / kg 1kg 99.5 10 ton per month Nanjing Deda New Material Technology Co., Ltd
Levamisole pictures 2024-03-19 Levamisole
14769-73-4
US $10.00-1.00 / kg 1kg 98% 1200tons Hebei Dangtong Import and export Co LTD
Levamisole pictures 2024-03-19 Levamisole
14769-73-4
US $13.00-1.00 / kg 1kg 99% 300tons Hebei Dangtong Import and export Co LTD
  • Levamisole pictures
  • Levamisole
    14769-73-4
  • US $10.00-5.00 / kg
  • 99.5
  • Nanjing Deda New Material Technology Co., Ltd
  • Levamisole pictures
  • Levamisole
    14769-73-4
  • US $10.00-1.00 / kg
  • 98%
  • Hebei Dangtong Import and export Co LTD
  • Levamisole pictures
  • Levamisole
    14769-73-4
  • US $13.00-1.00 / kg
  • 99%
  • Hebei Dangtong Import and export Co LTD
L-6-PHENYL-2,3,5,6-TETRAHYDROIMIDAZOL(2,1-B) THIAZOLE IMMUNOPURE(R) PHOSPHATASE SUPPRESSOR LEVAMISOLE (s)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole l-tetramisole 6-PHENYL-2,3,5,6-TETRAHYDROIMIDAZO[2,1-B]THIAZOLE (LEVAMISOLE) (6S)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole Ketrax Imidazo2,1-bthiazole, 2,3,5,6-tetrahydro-6-phenyl-, (6S)- (S)-(-)-Levamisole Tetramisole cas 14769-73-4 (skype:lisa_21819) Levamisole powder hot sale Levamisole Levamisole Veterinary drugs Levamisole Wickr jane8886 Levamisole USP/EP/BP Veterinary Drugs Levamisole 99% Pure Levamisole Levamisole Wickr Levamisole/Levamisole base Levamisole (S)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole LevamisoleQ: What is Levamisole Q: What is the CAS Number of Levamisole Q: What is the storage condition of Levamisole Q: What are the applications of Levamisole Levamisole cas 14769-73-4 LEVAMISOLE BASE lepuron levomysol (S)-6-phenyl-2,3,5,6-tetrahydroiMidazo[2,1-b]thiazole tert-butylN-(1-amino-2-oxoazetidin-5-yl)carbamate 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3H-BENZO[D]IMIDAZOLE 14769-73-4 114769-73-4 C11H8ClN2S 14769-73-4