Clinical data | |
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Trade names | Vansil |
AHFS/Drugs.com | Micromedex Detailed Consumer Information |
Routes of administration | By mouth |
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Pharmacokinetic data | |
Bioavailability | Readily absorbed when taken by mouth |
Metabolism | liver |
Elimination half-life | 1 to 2.5h |
Excretion | mainly in urine |
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ECHA InfoCard | 100.040.491 |
Chemical and physical data | |
Formula | C14H21N3O3 |
Molar mass | 279.3 g·mol−1 |
3D model (JSmol) | |
Chirality | Racemic mixture |
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Oxamniquine, sold under the brand name Vansil among others, is a medication used to treat schistosomiasis due to Schistosoma mansoni . [1] Praziquantel, however, is often the preferred treatment. [2] It is given by mouth and used as a single dose. [2]
Common side effects include sleepiness, headache, nausea, diarrhea, and reddish urine. [1] It is typically not recommended during pregnancy, if possible. [1] Seizures may occur and therefore caution is recommended in people with epilepsy. [1] It works by causing paralysis of the parasitic worms. [3] It is in the anthelmintic family of medications. [4]
Oxamniquine was first used medically in 1972. [5] It is on the World Health Organization's List of Essential Medicines. [6] It is not commercially available in the United States. [4] It is more expensive than praziquantel. [7]
Oxamniquine is used for treatment of schistosomiasis. According to one systematic review, praziquantel is the standard treatment for S. mansoni infections and oxamniquine also appears effective. [8]
It is generally well tolerated following oral doses. Dizziness with or without drowsiness occurs in at least a third of patients, beginning up to three hours after a dose, and usually lasts for up to six hours. Headache and gastrointestinal effects, such as nausea, vomiting, and diarrhoea, are also common.[ citation needed ]
Allergic-type reactions, including urticaria, pruritic skin rashes, and fever, may occur. Liver enzyme values have been raised transiently in some patients. Epileptiform convulsions have been reported, especially in patients with a history of convulsive disorders. Hallucinations and excitement have occurred rarely.[ citation needed ]
A reddish discoloration of urine, probably due to a metabolite of oxamniquine, has been reported.[ citation needed ]
Oxamniquine is not recommended during pregnancy. [1]
Peak plasma concentrations are achieved one to three hours after a dose, and the plasma half-life is 1.0 to 2.5 hours.[ citation needed ]
It is extensively metabolised to inactive metabolites, principally the 6-carboxy derivative, which are excreted in the urine. About 70% of a dose of oxamniquine is excreted as the 6-carboxy metabolite within 12 hours of a dose; traces of the 2-carboxy metabolite have also been detected in the urine.
It is an anthelmintic with schistosomicidal activity against Schistosoma mansoni , but not against other Schistosoma spp. Oxamniquine is a potent single-dose agent for treatment of S. mansoni infection, and it causes worms to shift from the mesenteric veins to the liver, where the male worms are retained; the female worms return to the mesentery, but can no longer release eggs. [9]
Oxamniquine is a semisynthetic tetrahydroquinoline and possibly acts by DNA binding, resulting in contraction and paralysis of the worms and eventual detachment from terminal venules in the mesentry, and death. Its biochemical mechanisms are hypothesized to be related to an anticholinergic effect, which increases the parasite's motility, as well as inhibiting the synthesis of nucleic acids. Oxamniquine acts mainly on male worms, but also induces small changes on a small proportion of females. Like praziquantel, it promotes more severe damage of the dorsal tegument than of the ventral surface. The drug causes the male worms to shift from the mesenteric circulation to the liver, where the cellular host response causes its final elimination. The changes caused in the females are reversible and are due primarily to the discontinued male stimulation rather than the direct effect of oxamniquine.[ citation needed ]
Oxamniquine was first described by Kaye and Woolhouse in 1972 as a metabolite of the compound UK 3883 (2-isopropylaminomethyl-6-methyl-7-nitro-1,2,3,4-tetrahydroquinoline). Initially, it was prepared by enzymatic hydroxylation via the fungus Aspergillus sclerotiorum . In 1979, Pfizer at Sandwich was presented with the Queen's Award for Technological Achievement in recognition of the outstanding contribution made to tropical medicine by MANSIL (oxamniquine).[ citation needed ]
Oxamniquine contains a stereocenter and consists of two enantiomers. This is a racemate, i.e. a 1: 1 mixture of ( R ) - and the ( S ) - form:
Enantiomers of oxamniquine | |
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(R)-isomer | (S)-isomer |
Schistosomiasis, also known as snail fever, bilharzia, and Katayama fever, is a disease caused by parasitic flatworms called schistosomes. The urinary tract or the intestines may be infected. Symptoms include abdominal pain, diarrhea, bloody stool, or blood in the urine. Those who have been infected for a long time may experience liver damage, kidney failure, infertility, or bladder cancer. In children, it may cause poor growth and learning difficulty.
Schistosoma is a genus of trematodes, commonly known as blood flukes. They are parasitic flatworms responsible for a highly significant group of infections in humans termed schistosomiasis, which is considered by the World Health Organization as the second-most socioeconomically devastating parasitic disease, with hundreds of millions infected worldwide.
Praziquantel (PZQ), sold under the brandname Biltricide among others, is a medication used to treat a number of types of parasitic worm infections in mammals, birds, amphibians, reptiles, and fish. In humans specifically, it is used to treat schistosomiasis, clonorchiasis, opisthorchiasis, tapeworm infections, cysticercosis, echinococcosis, paragonimiasis, fasciolopsiasis, and fasciolosis. It should not be used for worm infections of the eye. It is taken by mouth.
Helminthiasis, also known as worm infection, is any macroparasitic disease of humans and other animals in which a part of the body is infected with parasitic worms, known as helminths. There are numerous species of these parasites, which are broadly classified into tapeworms, flukes, and roundworms. They often live in the gastrointestinal tract of their hosts, but they may also burrow into other organs, where they induce physiological damage.
Amoxicillin/clavulanic acid, also known as co-amoxiclav or amox-clav, sold under the brand name Augmentin, among others, is an antibiotic medication used for the treatment of a number of bacterial infections. It is a combination consisting of amoxicillin, a β-lactam antibiotic, and potassium clavulanate, a β-lactamase inhibitor. It is specifically used for otitis media, streptococcal pharyngitis, pneumonia, cellulitis, urinary tract infections, and animal bites. It is taken by mouth or by injection into a vein.
Hymenolepiasis is infestation by one of two species of tapeworm: Hymenolepis nana or H. diminuta. Alternative names are dwarf tapeworm infection and rat tapeworm infection. The disease is a type of helminthiasis which is classified as a neglected tropical disease.
Albendazole is a broad-spectrum anthelmintic and antiprotozoal agent of the benzimidazole type. It is used for the treatment of a variety of intestinal parasite infections, including ascariasis, pinworm infection, hookworm infection, trichuriasis, strongyloidiasis, taeniasis, clonorchiasis, opisthorchiasis, cutaneous larva migrans, giardiasis, and gnathostomiasis, among other diseases.
Schistosoma japonicum is an important parasite and one of the major infectious agents of schistosomiasis. This parasite has a very wide host range, infecting at least 31 species of wild mammals, including 9 carnivores, 16 rodents, one primate (human), two insectivores and three artiodactyls and therefore it can be considered a true zoonosis. Travelers should be well-aware of where this parasite might be a problem and how to prevent the infection. S. japonicum occurs in the Far East, such as China, the Philippines, Indonesia and Southeast Asia.
Schistosoma mansoni is a water-borne parasite of humans, and belongs to the group of blood flukes (Schistosoma). The adult lives in the blood vessels near the human intestine. It causes intestinal schistosomiasis. Clinical symptoms are caused by the eggs. As the leading cause of schistosomiasis in the world, it is the most prevalent parasite in humans. It is classified as a neglected tropical disease. As of 2021, the World Health Organization reports that 236.6 million people have schistosomiasis and most of it is due to S. mansoni. It is found in Africa, the Middle East, the Caribbean, Brazil, Venezuela and Suriname.
Tribendimidine is a broad-spectrum anthelmintic agent developed in China, at the National Institute of Parasitic Diseases in Shanghai. It is a derivative of amidantel.
Schistosoma intercalatum is a parasitic worm found in parts of western and central Africa. There are two strains: the Lower Guinea strain and the Zaire strain. S. intercalatum is one of the major agents of the rectal form of schistosomiasis, also called bilharzia. It is a trematode, and being part of the genus Schistosoma, it is commonly referred to as a blood-fluke since the adult resides in blood vessels.
Niclosamide, sold under the brand name Niclocide among others, is an anthelmintic medication used to treat tapeworm infestations, including diphyllobothriasis, hymenolepiasis, and taeniasis. It is not effective against other worms such as flukes or roundworms. It is taken by mouth.
Lamivudine/zidovudine, sold under the brand name Combivir among others, is a fixed-dose combination antiretroviral medication used to treat HIV/AIDS. It contains two antiretroviral medications, lamivudine and zidovudine. It is used together with other antiretrovirals. It is taken by mouth twice a day.
Levamisole, sold under the brand name Ergamisol among others, is a medication used to treat parasitic worm infections, specifically ascariasis and hookworm infections. It is taken by mouth.
A Schistosomiasis vaccine is a vaccine against Schistosomiasis, a parasitic disease caused by several species of fluke of the genus Schistosoma. No effective vaccine for the disease exists yet. Schistosomiasis affects over 200 million people worldwide, mainly in rural agricultural and peri-urban areas of the third world, and approximately 10% suffer severe health complications from the infection. While chemotherapeutic drugs, such as praziquantel, oxamniquine and metrifonate both no longer on the market, are currently considered safe and effective for the treatment of schistosomiasis, reinfection occurs frequently following drug treatment, thus a vaccine is sought to provide long-term treatment. Additionally, experimental vaccination efforts have been successful in animal models of schistosomiasis.
Stibophen is an anthelmintic originally developed by Bayer that is used as a treatment for schistosomiasis by intramuscular injection. It is classified as a trivalent antimony compound. Brand names include Fouadin/Fuadin.
Schistosoma mekongi is a species of trematodes, also known as flukes. It is one of the five major schistosomes that account for all human infections, the other four being S. haematobium, S. mansoni, S. japonicum, and S. intercalatum. This trematode causes schistosomiasis in humans.
Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. They may also be called vermifuges or vermicides. Anthelmintics are used to treat people who are infected by helminths, a condition called helminthiasis. These drugs are also used to treat infected animals.
Mass deworming, is one of the preventive chemotherapy tools, used to treat large numbers of people, particularly children, for worm infections notably soil-transmitted helminthiasis, and schistosomiasis in areas with a high prevalence of these conditions. It involves treating everyone – often all children who attend schools, using existing infrastructure to save money – rather than testing first and then only treating selectively. Serious side effects have not been reported when administering the medication to those without worms, and testing for the infection is many times more expensive than treating it. Therefore, for the same amount of money, mass deworming can treat more people more cost-effectively than selective deworming. Mass deworming is one example of mass drug administration.