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Benzimidazoles were originally developed as plant fungicides and later as veterinary and human anthelmintics. The family of benzimidazoles with anthelmintic activity includes thiazolyl benzimidazoles and benzimidazole carbamates. The benzimidazoles show a broad spectrum of activity against helminth parasites. Well known benzimidazoles with activity against helminths are for example thiabendazole; cambendazole; and benzimidazole carbamates, such as parbendazole (U.S. Pat. No. 3,480,642), mebendazole (U.S. Pat. No. 3,657,267), flubendazole (U.S. Pat. No. 3,657,267), fenbendazole (U.S. Pat. No. 3,954,791), oxfendazole (U.S. Pat. No. 3,929,821), oxibendazole (U.S. Pat. No. 3,574,845), albendazole (U.S. Pat. No. 3,915,986), ricobendazole ( albendazole sulfoxide) (U.S. Pat. No. 3,915,986) and luxabendazole (U.S. Pat. No. 4,639,463), all of which differ in the substituents on the parent benzimidazole nucleus.
Benzimidazoles are believed to owe their activity to the fact that they block the polymerization of beta-tubulin into microtubules. This affects the transport functions of cells within the parasite and ultimately kills the parasite.
Phenylguanidine prodrugs that are metabolically transformed into anthelmintic benzimidazoles have also been developed. Febantel (U.S. Pat. No. 3,993,682), for example, is a prodrug that is converted into fenbendazole, and netobimin (U.S. Pat. No. 4,406,893) yields albendazole. Albendazole is an anthelmintic medication used in the treatment of infections of the body caused by tapeworms. The medication works by preventing newly hatched worms from growing and multiplying from within the body. As with most anthelmintic medications, there are certain side effects associated with treatment.
Efforts regarding benzimidazole prodrugs were undertaken in the context of the use of the benzimidazoles in the combat of systemic infections, for example with the larval stage of the cestodes, Echinococcus multicularis and E. granulosis . In these cases plasma and tissue levels of the drugs are important since, in order to act systemically, the benzimidazoles have to be taken up into the bloodstream.
Certain albendazole prodrugs are described by Hernández-Luis et al. in Bioorganic & Medicinal Chemistry Letters, 11, 1359-1362, 2001. Hernández-Luis et al. attempted to enhance the solubility of albendazole by synthesizing three N-acyl and two N-alkoxycarbonyl derivatives. These derivatives were developed mainly in the context of the use of albendazole products for some tissue dwelling infestations such as trichinellosis, hydrated disease (echinococcsis) and neurocysticerosis, where high doses and long treatment are required due to the poor solubility and absorption of albendazole. Before taking Albendazole, tell your doctor if you have ever suffered from liver disease or any type of liver condition as you may not be able to use this medication. This medication is classified as FDA pregnancy category C and it may cause harm to an unborn baby. It is also unknown whether or not the drug is secreted into breast milk, and it is recommended to use extreme caution if you are nursing while using this medication. Also, consult with your doctor if you have ever had an allergic reaction to any type of food or medication before using this drug.
Mannich bases of albendazole and fenbendazole were prepared by Dhaneshwar et al., Indian drugs, 28(1), 24-26, 1990, using various secondary amines such as dimethylamine, dipropylamine, pyrrolidine, piperazine, etc. Further Mannich bases are described in Garst et al. (U.S. Pat. No. 6,093,734). However, actual activity has not been demonstrated for the Mannich bases, and these derivative show very low stability in water.
A water soluble prodrug of albendazole manufacturer exists, namely netobimin. But although netobimin is water soluble, it has been reported to cause embryonal toxicity.
In WO9312124 another class of benzimidazoles is discussed, namely substituted 2-[[(3,4-dialkoxy-2-pyridinyl)-methyl]sulfonyl]-1(H)-benzimi dazole-1-yl compounds. These benzimidazoles are gastric acid secretion inhibitors (proton pump inhibitors) and structurally resemble well-known gastric acid secretion inhibitors like omeprazole and lansoprazole. In contrast to the benzimidazole carbamates, which are practically insoluble in water, the benzimidazole proton pump inhibitors are markedly more soluble in water. For example, omeprazole has a solubility of 500 µg/mL Unfortunately, there are a number of side effects associated with using albendazole. Some of these side effects include nausea, stomach pain, vomiting, temporary hair loss, dizziness, headache, unusual weakness, easy bruising and bleeding, sore throat, fever, skin rash, body aches, flu-like symptoms and severe skin blistering. While these are considered the most common side effects associated with this drug, they only affect a small amount of users.
If you are allergic to albendazole or mebendazole, you should not use this medication as it can cause severe internal damage to some users. This medication has been known to lower the body's ability to fight infection and it is recommended that users stay away from anyone with an illness or disease until they have completed treatment. Regular blood tests will be required to ensure that your blood-cell levels remain at a healthy level throughout the course of your treatment, so consult with your doctor about an appropriate schedule.The compounds of the invention are highly soluble and stable in water. For example, a mixture of (5- and 6-phenylsulfanyl-1-phosphonooxymethyl-1(H)-benzoimidazol-2-y l)-carbamic acid methyl esters di-sodium salts has a solubility in water of 132 mM (67 g/L). Furthermore, other compounds according to the invention such as N-phosphonooxymethyl substituted albendazole, mebendazole, flubendazole and luxabendazole sodium salts have aqueous solubilities of at least 50 mM.
Always use albendazole tablets exactly as it was prescribed by your doctor and never in dosages larger than what has been recommended on the label. The medication is administered in tablet form and should be taken with food and a full glass of water. Alebendazole is sometimes used as a cycled medication, meaning that treatment may occur for four weeks followed directly by two weeks of non-treatment. Store this medication away from sources of moisture and at room temperature for the best results.If you experience any of the above side effects, contact your doctor immediately.
If an overdose is suspected, contact the poison control center at (800) 222-1222 and head directly to the nearest emergency room.
Albendazole is meant in the treatment of the above ailments only and should not be used for any other medical purpose unless specifically prescribed by a doctor. source:townhallalbendazole tablets
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