Name | pyrante |
Synonyms | pyrante banminth pyrequan PYRANTELUM Pyrantel Base PYRANTEL PARMOATE 4,5,6-tetrahydro-1-methyl-2-(2-(2-thienyl)ethenyl)-(e)-pyrimidin 1-methyl-2-[2-(thiophen-2-yl)ethenyl]-1,4,5,6-tetrahydropyrimidine Pyrimidine, 1,4,5,6-tetrahydro-1-methyl-2-(1E)-2-(2-thienyl)ethenyl- 1-methyl-2-[(E)-2-(thiophen-2-yl)ethenyl]-1,4,5,6-tetrahydropyrimidine |
CAS | 15686-83-6 |
EINECS | 2397741 |
InChI | InChI:1S/C11H14N2S/c1-13-8-3-7-12-11(13)6-5-10-4-2-9-14-10/h2,4-6,9H,3,7-8H2,1H3/b6-5+ |
Molecular Formula | C23H16O6.C11H14N2S |
Molar Mass | 594.685 |
Density | 1.13±0.1 g/cm3(Predicted) |
Melting Point | 178-179° |
Boling Point | 324.4±44.0 °C(Predicted) |
Flash Point | 356.5°C |
Vapor Presure | 2.13E-17mmHg at 25°C |
pKa | 12.60±0.20(Predicted) |
Storage Condition | 2-8°C |
Physical and Chemical Properties | Commonly used dihydroxynaphthalate and tartrate, thiacil dihydronaphthalate is a light yellow powder; odorless and tasteless. It is slightly soluble in dimethylformamide, slightly soluble in ethanol, and almost insoluble in water, while thiacil tartrate is easily soluble in water. |
intestinal anthelmintic | also known as anti-insect spirit, is a broad-spectrum intestinal anthelmintic. This product is light yellow crystalline powder, odorless, tasteless, soluble in alkali, insoluble in water. Intestinal parasites nerve muscle block, can paralysis, so that it is completely excreted in vitro. It is clinically used to drive Ascaris, pinworm and hookworm, and its therapeutic effect is better than that of drugs such as buyanling, shuyanling and benzophenin. It can also be used to drive intestinal worms in livestock. Usage: anthelmintic 5~10mg/kg/time; Hookworm, the dosage of the same, even served 3 days; Pinworm, 5 mg/kg/day even served 1 week. Taking this product is calculated according to The Matrix, with half an empty stomach is better, do not take laxatives. This medicine may have a slight reaction, generally do not need to deal. Pregnant women, coronary heart disease, ulcer disease patients with caution, suffering from other acute patients slow use. |
physical and chemical properties | commonly used in its BIS-hydroxynaphthalate and tartrate, di-hydroxynaphthalate thiazine is light yellow powder; Odorless, tasteless. It is slightly soluble in dimethylformamide, slightly soluble in ethanol, and almost insoluble in water, while thiazine tartrate is soluble in water. |
History of research and development | in the mid 50 s, Pfizer researchers set up a screening program for new anti-entero-drugs, to expand the screening laboratory mice were inoculated with three different microorganisms and as a result a large number of compounds were screened, only compound I, showing evidence of activity. But given orally to sheep, it has only little activity, probably because of its hydrolysis of the compound. Since then, it has been synthesized, named 2-thenylthiol and 2-imidazolidone. Congeners of compound I were designed to resist hydrolysis and synthesized at Pfizer research center. When the sulfur atom bridge between the two rings is substituted with a methylene group, the compound is made to act on various intestinal parasites that infect sheep. Since this compound is toxic, it is synthesized in the same species. Optimal activity against various nematodes is obtained by increasing the tetrahydropyrimidine ring, e.g. This is an oral active broad-spectrum anti-intestinal insect drug. It is effective against roundworms, hookworms and nematodes in humans and animals. Phenopyrimidine (oxantel), one of the thiopyrimidine analogs, was prepared to examine the relationship between aromatic ring substitution and intestinal insect resistance. In mice it is only 1/10 of the potency of the thiazine against the nematode, but it differs from the thiazine against the tapeworm. It is also active when tested in dogs infected with nematodes, and this activity compensates for its narrow spectrum of anti-worm activity and becomes a major clinical application. |
pharmacological effects | This product is a depolarizing neuromuscular blocking agent, which can inhibit the cholinesterase of the worm, the accumulation of acetylcholine in the cholinergic nerve endings, which causes the body muscle contraction and spastic paralysis, so that can not attach to the intestinal wall and fecal discharge from the body, does not cause biliary obstruction or intestinal obstruction. For broad-spectrum, high efficiency, low toxicity of gastrointestinal nematode repellent, chicken, dog and other digestive tract nematodes have a good anthelmintic effect, this product is piperazine, four imidazole, thiabendazole and phenethylamine have strong insecticidal action and low toxicity. Monogastric animals oral thiamine tartrate, easy to fully absorb. Dihydroxynaphthalic acid thiopyrimidine is difficult to dissolve in water, the intestinal tract rarely absorbed, which can reach the end of the large intestine to play a good role in driving pinworm. |
pharmacokinetics | is rarely absorbed orally. After oral administration of 1 to 3 hours, the blood drug concentration reached the peak value, and the peak value of the blood drug concentration was 0.05~0.13mg/L when 11 mg/kg was orally administered once. 50% ~ 75% to the prototype drug from the feces, about 7% to the prototype drug from the bile duct and urine discharge. |
indication | thiamine is suitable for hookworm, roundworm, pinworm or mixed infection, and has good curative effect. Among them, the curative effect of hookworm is better than that of American hookworm, and it also has certain curative effect on whipworm. It is rarely absorbed after oral administration, so the systemic toxicity is very low. In addition to the treatment of cattle, sheep and dogs, thiopyrimidine tartrate can also be used as a good preventive drug for gastrointestinal parasites, which can reduce various parasitic infections. In particular, the use of thiopyrimidine bis-hydroxynaphthalate is indicated for the eradication of Enterobius vermicularis infection in post-digestive tract of animals. |
adverse reaction | (1) the toxicity of thiopyrimidine is very small, and there is no host toxic reaction when the dose is 5~7 times higher than the therapeutic dose. There was no adverse clinical reaction to pregnant and young animals. (2) the tolerance of horse to tartrate is worse than that of BIS-hydroxynaphthalate, and the reaction of profuse sweat and Movement Disorder can be seen during poisoning, movement disorder was noted. |
drug interaction | ① combination with levamisole can treat severe hookworm infection, but the toxicity is also enhanced. (2) with piperazine, can produce mutual antagonism. ③ It is prohibited to combine with neuroleptics, muscle relaxants (such as carnosine), other cholinergic drugs (such as pilocarpine) and anticholinesterase drugs (such as physostigmine and neostigmine), because of the strong nicotinic effect of the host, the toxicity is enhanced. (4) combined with organic phosphorus or diethylamine, can enhance the toxicity of each other. |
note | (1) because of its cholinergic-like effect, this product is contraindicated in pregnant and debilitating animals (especially thiazine tartrate). (2) because of the ease of absorption and the narrow range of safety of thipyrimidine tartrate, it must be accurately measured when used in large animals (especially horses). (3) due to the light deterioration of thiopyrimidine, the suspension of the BIS-hydroxynaphthalate should be used up in time, and the tartrate salt is not allowed to be formulated in foreign countries. It is used as a premix and mixed in the feed for administration. |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |