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
- MOL File:
- 14769-73-4.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/29 15:17:36
| 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) |
| EPA Substance Registry System | Levamisole (14769-73-4) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  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 Chemical Properties,Uses,Production
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) 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.
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).
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).
Levamisole Preparation Products And Raw materials
Raw materials
1of2
chevron_rightPreparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Manasvi Life Sciences | +91-9391326151 +91-9490072008 | Hyderabad, India | 39 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| Hebei Mojin Biotechnology Co., Ltd | +8613288715578 | China | 12452 | 58 | Inquiry |
| Hebei Yanxi Chemical Co., Ltd. | +86-17531190177; +8617531190177 | China | 5873 | 58 | Inquiry |
| Wuhan Ruichi Technology Co., Ltd | +8613545065237 | China | 161 | 58 | Inquiry |
| Hebei Weibang Biotechnology Co., Ltd | +8615350571055 | China | 5251 | 58 | Inquiry |
| Nanjing Deda New Material Technology Co., Ltd | +8613223293093 | China | 80 | 58 | Inquiry |
| Dorne Chemical Technology co. LTD | +86-86-13583358881 +8618560316533 | China | 3146 | 58 | Inquiry |
Related articles
- The brief introduction of Levamisole
- Levamisole is an anthelmintic agent effective against A. lumbricoides and Ancylostoma duodenale.
- Jun 26，2024
- Synthesis and Toxicology of Levamisole
- Levamisole is commonly used for deworming of various animals and is effective against both adults and larvae.
- Oct 11，2022
14769-73-4(Levamisole)Related Search:
1of4
chevron_right