Tetramisole hydrochloride
Tetramisole hydrochloride Basic information
- Product Name:
- Tetramisole hydrochloride
- Synonyms:
-
- (+-)-2,3,5,6-tetrahydro-6-phenylimidazo(2,1-b)thiazolemonohydrochloride
- (+-)-anthelvet
- 1-b)thiazole,2,3,5,6-tetrahydro-6-phenyl-,monohydrochloride,(+-)-imidazo(
- anthelvet
- bayer9051
- citarin
- dl-6-phenyl-2,3,5,6-tetrahydroimidazole(2,1-b)thiazole-hydrochloride
- dl-tetramisolehydrochloride
- CAS:
- 5086-74-8
- MF:
- C11H13ClN2S
- MW:
- 240.75
- EINECS:
- 225-799-5
- Product Categories:
-
- API
- Veterinaries
- Aromatics
- Heterocycles
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Sulfur & Selenium Compounds
- METRIPHONATE
- 5086-74-8
- Mol File:
- 5086-74-8.mol
Tetramisole hydrochloride Chemical Properties
- Melting point:
- 266-267 °C(lit.)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Methanol (Slightly), Water (Slightly, Heated)
- form
- Solid
- color
- White to Off-White
- Water Solubility
- 200 g/L (20 ºC)
- Merck
- 13,5480
- BRN
- 4358989
- Stability:
- Hygroscopic
- InChI
- InChI=1S/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
- InChIKey
- LAZPBGZRMVRFKY-UHFFFAOYSA-N
- SMILES
- C1N2C(=NC(C2)C2=CC=CC=C2)SC1.[H]Cl
- CAS DataBase Reference
- 5086-74-8(CAS DataBase Reference)
Safety Information
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22-36/37/38-20/21/22
- Safety Statements
- 26-36
- WGK Germany
- 3
- RTECS
- NJ5950000
- HS Code
- 29349990
- Toxicity
- LD50 in mice, rats (mg/kg): 22, 24 i.v.; 84, 130 s.c.; 210, 480 orally (Thienpoint)
MSDS
- Language:English Provider:DL-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole hydrochloride
- Language:English Provider:SigmaAldrich
- Language:English Provider:ACROS
Tetramisole hydrochloride Usage And Synthesis
Chemical Properties
Tetraimidazole hydrochloride is a white to pale cream crystalline powder, bitter and astringent, easily soluble in water , Methanol, slightly soluble in ethanol, insoluble in acetone. acid solutions are stable; however, hydrolysis occurs under alkaline conditions. The rate of hydrolysis increases with pH and temperature. It is used as levamisole intermediate, anthelmintic drug.
Uses
Tetramisole hydrochloride is an inhibitor of alkaline phosphatases, is a high purity antiparasitic. It is suitable for inhibition of various alkaline phosphatase (i.e., liver, kidney, placenta, bone and tumor)(Intestinal alkaline phosphatases are only slightly inhibited.). Tetramisole has biological response modifier with anthelmintic activity. Anthelmintic (nematodes); immunomodulator.
Definition
ChEBI: Tetramisole hydrochloride is an organic molecular entity. It is a broad-spectrum veterinary anthelmintic with high efficiency and low toxicity.
Application
Tetramisole is an alkaline phosphatase inhibitor. It is a racemic mixture of (+) and (-) isomers. The (-) isomer (levamisole) accounts for most of the biological activity of tetramisole.
Tetramisole has been used to inhibit alkaline phosphatase in the effective range of 0.4 – 2 mM. Inhibition of intestinal alkaline phosphate requires higher concentrations. In addition to its use in enzyme and protein phosphorylation studies, tetramisole has been used to study membrane, tissue and animal systems.
Tetramisole is an anthelminthic agent used in veterinary applications to treat helminth or worm infections.
brand name
Ergamisol (Janssen).
in vitro
Tetramisole hydrochloride at 67.5 mg/kg is 88.8% effective against immature and 99.7% effective against adult Libyostrongylus douglassi of the ostrich. A dose of up to 408 mg/kg tetramisole hydrochloride had no adverse effects on young birds but at 529 mg/kg was lethal to both chicks and adult ostriches. The efficacy of pyrantel tartrate was erratic. At 50 - 60 mg/kg it was 72.3% effective against immatures and 50.2% effective against adult worms. At 100 mg/kg it fell to 43.6% against immature, but rose to 77.3% against adult worms. Pyrantel tartrate at 100 mg/kg caused the death .of three out of four chicks. The macroscopic lesions of the disease ""vrotmaag"" caused by L. douglassi are descriptionbed as well as some of the other pathological lesions observed at autopsy.
Mode of action
Tetramisole HCl inhibits parasitic worm growth by acting as an agonist to nicotinic acetylcholine receptors leading to paralysis. The mechanism of action for anticancer activity is unknown.
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