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Levamisole hydrochloride

Levamisole hydrochloride structure

CAS No:
16595-80-5
Formula:
C11H12N2S.ClH
Chemical Name:
Levamisole hydrochloride
Synonyms:
Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-,hydrochloride (1:1),(6S)-;Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-,monohydrochloride,(S)-;Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-,monohydrochloride,(-)-;Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-,monohydrochloride,(6S)-;l-Tetramisole hydrochloride;Decaris;Levamisole hydrochloride;Tramisol;Tramisole;Levomysol hydrochloride;Ripercol L;Citarin L;KW 2LE-T;(-)-Levamisole hydrochloride;L-Narpenol;Dekaris;Nilverm forte;Meglum;Solaskil;Ergamisole;Levadin;R 12654;Levasole;Spartakon L;Levacide;Nemicide;Ascaridil;Ergamisol;NSC 177023;Century-Ace;(-)-Tetramisole hydrochloride;Niratil;(7S)-7-Phenyl-4-thia-1,6-diazabicyclo[3.3.0]oct-5-ene hydrochloride;(6S)-6-Phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole hydrochloride;24593-45-1;39170-95-1;74191-78-9;42440-03-9
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

Levamisole Hcl is an anthelmintic and immunomodulator belonging to a class of synthetic imidazothiazole derivatives.IC50 value: Target: Levamisole suppresses the production of white blood cells, resulting in neutropenia and agranulocytosis. With the increasing use of levamisole as an adulterant, a number of these complications have been reported among cocaine users [1] [2]. Levamisole reversibly and noncompetitively inhibits most isoforms of alkaline phosphatase (e.g., human liver, bone,

Levamisole hydrochloride is an organic molecular entity.|Levamisole Hydrochloride is the hydrochloride salt of the synthetic imidazothiazole derivative levamisole with anthelminthic and immunomodulating activities. In immunosuppressed states, levamisole may restore immune function by: 1) stimulating antibody formation, 2) stimulating T-cell activation and proliferation, 3) potentiating monocyte and macrophage phagocytosis and chemotaxis and 4) increasing neutrophil mobility, adherence, and chemotaxis.|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 hydrochloride Basic Attributes

Molecular Weight：

240.75200

Exact Mass：

240.04900

EC Number：

240-654-6

UNII：

DL9055K809

NSC Number：

177023

DSSTox ID：

DTXSID7047518

NCI Thesaurus Code：

C610

HScode：

2933290090

Characteristics

PSA：

40.90000

XLogP3：

2.32160

Appearance：

white to almost white crystalline powder

Melting Point：

227-229 °C

Boiling Point：

344.4ºC at 760 mmHg

Flash Point：

162.1ºC

Water Solubility：

>36.1 [ug/mL]

Storage Conditions：

0-6ºC

Specific rotation：

(c = 1, H2O) [a]21D = - 126.2 ± 1.4°

Collision Cross Section：

143.9 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2811

wgk germany：

hazard class code：

R25

safety instructions：

S28-S45

RTECS Number：

NJ5960000

Marks：

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)：

Missing Phrase - N15.00950417

Hazard Statements：

H301

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P264, P270, P273, P281, P301+P310, P308+P313, P314, P321, P330, P405, and P501|Aggregated GHS information provided by 299 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P301+P310, P314, P321, P330, P405, and P501

Drug Information

Drug Indication：

Treatment of glomerulonephritis and nephrotic syndrome

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.)|Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)|Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)

MeSH Entry Terms：

Decaris

Levamisole hydrochloride Use and Manufacturing

Methods of Manufacturing

In 1000 ml four-mouth bottle into L-tetramisole 50g, inputs isopropanol 500g, heating is dissolved, add activated carbon 0.5g, sodium metabisulfite 0.75g stirring decolourizations 30 minutes, filtration, filtrate hydrogen chloride gas under stirring 9g, to pH4-5, filtering, levamisole hydrochloride dried to get 54.3g, yield 92.1percent, the target product without yellow block, long-term storage quality and stability.EXAMPLE X In 1000 ml four-mouth bottle into L-tetramisole 50g, inputs isopropanol 500g, heating is dissolved, add activated carbon 0.5g, sodium metabisulfite 0.75g stirring decolourizations 30 minutes, filtration, filtrate hydrogen chloride gas under stirring 9g, to pH4-5, filtering, levamisole hydrochloride dried to get 54.3g, yield 92.1percent, the target product without yellow block, long-term storage quality and stability.In 1000 ml four-mouth bottle into L-tetramisole 50g, inputs isopropanol 500g, heating is dissolved, add activated carbon 0.5g, sodium metabisulfite 0.75g stirring decolourizations 30 minutes, filtration, filtrate hydrogen chloride gas under stirring 9g, to pH4-5, filtering, levamisole hydrochloride dried to get 54.3g, yield 92.1percent, the target product without yellow block, long-term storage quality and stability.

Uses

1. Biological response modifier with anthelmintic activity. Anthelmintic (nematodes); immunomodulator.
2. Antifungal

Use Classification：

Human drugs -> Rare disease (orphan)|Human Drugs -> EU pediatric investigation plans|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

Food Additive Classes：

Veterinary Drug -> ANTHELMINTHIC_AGENT;

Computed Properties

Molecular Weight:240.75
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:240.0487973
Monoisotopic Mass:240.0487973
Topological Polar Surface Area:40.9
Heavy Atom Count:15
Complexity:246
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Material

2-Methoxyethanol

Price Analysis

Make your Levamisole hydrochloride purchase based on the price and market insights! ECHEMI provides professional market insights with prices for you to make a better choice. Learn more on Levamisole hydrochloride prices .

Drug Function and Efficacy

It selectively inhibits succinate dehydrogenase in the muscles of the worm, affects the anaerobic metabolism of the worm muscles, and reduces energy production; it depolarizes the nerve muscles, causing continuous muscle contraction and paralysis; its cholinergic effect is beneficial to the excretion of the worm; it may have an inhibitory effect on the microtubule structure of the worm; it has immune regulation and immune excitation functions.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Levamisole Hydrochloride Tablets
Ingredients	The main ingredient of this product is: Levamisole hydrochloride. Its chemical name is: (S)-(-)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride.
Indication	(1) It can be used in combination with pyrantel to treat severe hookworm infections and improve the effectiveness of expelling American hookworms. (2) It can be used in combination with thiabendazole to treat mixed intestinal nematode infections. (3) It can be used sequentially with diethylcarbamazine citrate to treat filarial infections. (4) It should not be used in combination with tetrachloroethylene to avoid increasing its toxicity.
Specifications	25mg
Manufacturer	Shanghai Jinbuhuan Lankao Pharmaceutical Co., Ltd.

Levamisole Hydrochloride Tablets
Ingredients	The main ingredient of this product is: Levamisole hydrochloride. Its chemical name is: (S)-(-)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride.
Indication	(1) It can be used in combination with pyrantel to treat severe hookworm infections and improve the effectiveness of expelling American hookworms. (2) It can be used in combination with thiabendazole to treat mixed intestinal nematode infections. (3) It can be used sequentially with diethylcarbamazine citrate to treat filarial infections. (4) It should not be used in combination with tetrachloroethylene to avoid increasing its toxicity.
Specifications	25mg
Manufacturer	Guangzhou Baiyunshan Huacheng Pharmaceutical Co., Ltd.

Levamisole Hydrochloride Tablets
Ingredients	The main ingredient of this product is: Levamisole hydrochloride. Its chemical name is: (S)-(-)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride.
Indication	(1) It can be used in combination with pyrantel to treat severe hookworm infections and improve the effectiveness of expelling American hookworms. (2) It can be used in combination with thiabendazole to treat mixed intestinal nematode infections. (3) It can be used sequentially with diethylcarbamazine citrate to treat filarial infections. (4) It should not be used in combination with tetrachloroethylene to avoid increasing its toxicity.
Specifications	25mg
Manufacturer	Chengdu Tongde Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

Chongqing Qingyang Pharmaceutical Co., Ltd.

China
Active
Shaanxi Hanjiang Pharmaceutical Group Co., Ltd.

China
Active
Youhua Pharmaceutical (Leshan) Co., Ltd.

China
Active

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