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Levamisole hydrochloride

CAS No.16595-80-5
Chemical Name:Levamisole hydrochloride
CBNumber:CB7853188
Molecular Formula:C11H13ClN2S
Formula Weight:240.75
MOL File:16595-80-5.mol

Levamisole hydrochloride Property

Melting point 266-267 °C(lit.)
alpha -128 º (c=5, H2O)
refractive index -126 ° (C=1, H2O)
Flash point 9℃
storage temp. 2-8°C
solubility Freely soluble in water, soluble in ethanol (96 per cent), slightly soluble in methylene chloride.
form Crystalline Powder
color White to almost white
biological source synthetic (organic)
Water Solubility 210 g/L (20 ºC)
Merck 14,5459
BRN 4358988
BCS Class 3/1
Stability Hygroscopic
InChI InChI=1/C11H12N2S.ClH/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10;/h1-5,10H,6-8H2;1H/t10-;/s3
InChIKey LAZPBGZRMVRFKY-HNCPQSOCSA-N
SMILES [C@H]1(N=C2SCCN2C1)C1=CC=CC=C1.Cl |&1:0,r|
LogP 1.845 (est)
CAS DataBase Reference 16595-80-5(CAS DataBase Reference)
FDA UNII DL9055K809
NCI Drug Dictionary Ergamisol
EPA Substance Registry System Levamisole hydrochloride (16595-80-5)
UNSPSC Code 41116107
NACRES NA.77

Safety

Hazard Codes :T,Xn,F
Risk Statements :25-20/21/22-39/23/24/25-23/24/25-11
Safety Statements :36/37/39-45-28A-36-36/37-16
RIDADR :UN 2811 6.1/PG 3
WGK Germany :3
RTECS :NJ5960000
F :10
HazardClass :6.1(b)
PackingGroup :III
HS Code :29349990

NFPA 704:

	3
0		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H301
Precautionary statements P301+P310+P330

Levamisole hydrochloride Price More Price(10)

Brand: Sigma-Aldrich(India)
Product number: L9756
Product name : (−)-Tetramisole hydrochloride
Purity: ≥99% (GC)
Packaging: 5G
Price: ₹5845.5
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: PHR1798
Product name : Levamisole Hydrochloride
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 250MG
Price: ₹16215.85
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: L9756
Product name : (−)-Tetramisole hydrochloride
Purity: ≥99% (GC)
Packaging: 10G
Price: ₹9699.2
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: L-025
Product name : (−)-Levamisole hydrochloride solution
Purity: 1.0?mg/mL in methanol (as free base), ampule of 1?mL, certified reference material, Cerilliant?
Packaging: 1ML
Price: ₹14656.6
Updated: 2022/06/14
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Brand: Sigma-Aldrich
Product number: 31742
Product name : Levamisol hydrochloride
Purity: VETRANAL?, analytical standard
Packaging: 250MG
Price: ₹6202.73
Updated: 2022/06/14
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Levamisole hydrochloride Chemical Properties,Usage,Production

Chemical Properties White to light yellow crystalline powder, odorless, bitter taste. Melting point 227-229℃. Soluble in water, methanol, ethanol and glycerol, slightly soluble in chloroform and aether; insoluble in acetone. Stable under acidic conditions, but easy to decompose and fail under alkaline conditions.
Originator Solaskil,Specia,France,1971
Uses Levamisole hydrochloride is an anthelmintic. The activity of levamisole is about twice as high as that of abscisicidal, and the toxicity and side effects are lower. Levamisole can cause muscle paralysis of roundworms and then excrete them in the feces. It is mainly used as an anti-worm and anti-hookworm.
Uses Biological response modifier with anthelmintic activity. Anthelmintic (nematodes); immunomodulator.
Definition ChEBI: Levamisole hydrochloride is an organic molecular entity.
Preparation Levamisole hydrochloride was prepared from racemic tetraimidazole by splitting, alkali analysis and acidification into salt.
Dibenzoyl-D-tartaric acid is boiled in water for 40min, hydrolyzed and neutralized with sodium hydroxide solution to pH 7.5, and then added to racemic tetraimidazole. The levamisole is precipitated by generating salt with bisbenzoyl-tartaric acid. After separation, add sodium hydroxide solution to PH=9 and decompose levamisole. Then dissolved in dilute hydrochloric acid solution, after decolorization by activated carbon, the filtrate was concentrated nearly dry, and crystallized by adding acetone and cooling to 0℃. Filtered and dried to obtain levamisole hydrochloride.
brand name Ergamisol (Janssen);Vermisol.
Therapeutic Function Antiinflammatory
Biochem/physiol Actions Shows both immunostimulant and immunosuppressant effects, depending on several controllable factors. Very effective in treatment of ascariasis (hookworm infestation). Useful in chemotherapy of colorectal cancers, possibly due to its stimulation of IL-1 production and direct activation of macrophages.
Pharmacology 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.
Pharmacokinetics Levamisole is rapidly absorbed from all routes of administration, with peak blood levels occurring within an hour followed by rapid metabolism and depletion principally via urinary excretion, with an elimination half-life of approximately 4 h.
Side effects Levamisole hydrochloride oral side effects are dose-related, mild and transient. The most common side effects are fever and gastrointestinal symptoms. Other possible side effects include: rash, changes in taste and smell, granulocytopenia and/or leukopenia, arthralgia/myalgia, convulsions, failure, peripheral neuropathy, tachycardia, thrombocytopenia, vasculitis, and vertigo.
Mode of action Levamisole is a cholinergic receptor agonist and elicits spastic muscle paralysis due to prolonged activation of the excitatory nicotinic acetylcholine receptors (nAChR) on nematode body wall muscle.
Toxicity evaluation Symptoms of levamisole toxicity mimic organophosphate toxicity (salivation, lacrimation, urination and defecation, hyperesthesia, seizures and irritability). There is no antidote for levamisole toxicity.
The World Health Organization reviewed hematological studies in animals and humans and derived acceptable daily intake for levamisole as 0.006 mg/kg body weight. This suggests a person can ingest 0.36 mg of levamisole/day over a lifetime without any appreciable risk.
levamisole