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Levamisole

Levamisole structure

CAS No:
14769-73-4
Formula:
C11H12N2S
Chemical Name:
Levamisole
Synonyms:
Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-,(6S)-;Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-,(S)-;(6S)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole;(-)-Tetramisole;Levamisole;l-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole;Levomysol;(-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2.1-b]thiazole;Ketrax;Levamisol;l-Tetramisole;L-Tetramisole;Vermisol 150;Lepuron;(S)-(-)-Levamisole;Wormicid;Totalon;Levovermax;Levipor;Anthelsol;Levomol;5: PN: WO2015086738 SEQID: 8 claimed sequence;Nilverm LV;(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole;(6S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole;(6S)-6-Phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole;53096-13-2;791526-27-7
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

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.

Solid

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.|Levamisole is an antihelminthic drug that was commonly used for the treatment of parasitic, viral, and bacterial infections. It was manufactured by Janssen and first used in 1969 as an agent to treat worm infestations Levamisole was approved by the FDA in 1990 as an adjuvant treatment for colon cancer. Prior to this, levamisole was used as an antirheumatic therapy in the 1970s and 1980s for patients with rheumatoid arthritis. Because of its immunomodulatory effects, this drug has been studied in the treatment of various immune-mediated diseases, with some studies showing positive results. This drug has also been used in combination with other drugs for the treatment of various cancers. Levamisole was withdrawn from the American market in 2000 due to its ability to cause serious adverse effects, including agranulocytosis. Interestingly, levamisole has been found as an adulterant in cocaine and can lead to a variety of adverse effects in individuals using this drug.|Levamisole is an anthelmintic drug. Co-administered with fluorouracil in the treatment of Dukes' stage C colon cancer, levamisole restores immune function through stimulating antibody formation, enhancing T-cell activity, and potentiating macrophage function. (NCI04)|An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6)

Levamisole Basic Attributes

Molecular Weight：

204.29

Exact Mass：

204.29

EC Number：

238-836-5

UNII：

2880D3468G

DSSTox ID：

DTXSID4023206

NCI Thesaurus Code：

C61609

ATC Code：

P - Antiparasitic products, insecticides and repellents

HScode：

2934100090

Characteristics

PSA：

40.9

XLogP3：

1.8

Appearance：

Solid

Density：

1.32±0.1 g/cm3(Predicted)

Melting Point：

60-61.5 °C

Boiling Point：

344.4±45.0 °C(Predicted)

Flash Point：

162.1±28.7 °C

Refractive Index：

1.713

Water Solubility：

Ethanol sl. sol. (mg/mL)

Storage Conditions：

0-6°C

Specific rotation：

D25 -85.1° (c = 10 in chloroform)

Collision Cross Section：

144.6 Å² [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]|138.2 Å² [M+H]+ [CCS Type: TW]|143.51 Å² [M+H]+

Safety Information

Transport codes：

UN 2811

Stability/Shelf Life：

Bulk: Levamisole appears to be stable in the bulk form at 60°C for at least four weeks. Solution: At 100 mg/mL concentrations in water and pH 7 buffer, the compound is stable for at least 9 days when stored at ambient temperature under normal laboratory illumination.

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (99.49%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 195 companies from 2 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity Summary：

LD50 = 40 mg/kg (Pigs, subcutaneous); LD50 = 180 mg/kg (rat, oral)

Protein Binding：

20-25%

Drug Information

Drug Indication：

For adjuvant treatment in combination with fluorouracil after surgical resection in patients with Dukes' stage C colon cancer. Also used to treat malignant melanoma and head/neck cancer.

Pharmacology：

Levamisole is a synthetic imidazothiazole derivative that has been widely used in treatment of worm infestations in both humans and animals. As an anthelmintic, it probably works by targeting the nematode nicotinergic acetylcholine receptor. As an immunomodulator, it appears that Levamisole is an immunostimulant which has been shown to increase NK cells and activated T-cells in patients receiving this adjuvantly along with 5FU for Stage III colon cancer.

MeSH：

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)|Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)|Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)

Absorption：

Levamisole is rapidly absorbed (2 hours) from the gastrointestinal tract.

Metabolism/Metabolites：

Primarily hepatic (extensive) with both active and inactive metabolites.

Biological Half-Life：

4.4-5.6 hours (biphasic)

Mechanism of Action：

The mechanism of action of levamisole as an antiparasitic agent appears to be tied to its agnositic activity towards the L-subtype nicotinic acetylcholine receptors in nematode muscles. This agonistic action reduces the capacity of the males to control their reproductive muscles and limits their ability to copulate. The mechanism of action of Levamisole as an anticancer drug in combination with fluorouracil is unknown. The effects of levamisole on the immune system are complex. The drug appears to restore depressed immune function rather than to stimulate response to above-normal levels. Levamisole can stimulate formation of antibodies to various antigens, enhance T-cell responses by stimulating T-cell activation and proliferation, potentiate monocyte and macrophage functions including phagocytosis and chemotaxis, and increase neutrophil mobility, adherence, and chemotaxis.

MeSH Entry Terms：

Decaris

Levamisole Use and Manufacturing

Uses

Biological response modifier.Ascariasis
Hookworm infection
Levamisole has been used in rheumatoid arthritis and some other conditions that are said to respond to its immunomodulatory activity.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. Levamisole has been used in dogs as a microfilaricide to treat Dirofilaria immitis infection in the past, but is rarely u

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Food Additive Classes：

Veterinary Drug -> ANTHELMINTHIC_AGENT;

Material

Levamisole hydrochloride

Dimethyl sulfoxide

Downstream Products

Levamisole hydrochloride

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