Oxamniquine
QP52AA02 (WHO) | |
Pharmacokinetic data | |
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Bioavailability | Readily absorbed when taken by mouth |
Metabolism | Liver |
Elimination half-life | 1 to 2.5h |
Excretion | Kidney |
Identifiers | |
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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,
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]
Medical uses
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]
Side effects
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]
Pharmacokinetics
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.
Mechanism of action
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
History
Oxamniquine was first described by Kaye and Woolhouse in 1972 as a
Brand names
- Vansil; (Pfizer) 250 mg capsules, syrup 250 mg/5 mL
- Mansil; 250 mg Tablets
Stereochemistry
Oxamniquine contains a stereocenter and consists of two enantiomers. This is a
Enantiomers of oxamniquine | |
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![]() (R)-isomer |
![]() (S)-isomer |
References
- ^ ISBN 978-9-2415-4765-9.
- ^ ISBN 978-0-12-381507-1. Archivedfrom the original on 20 December 2016.
- ISBN 978-0-7020-6338-1. Archivedfrom the original on 20 December 2016.
- ^ a b "Oxamniquine medical facts from Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
- ISBN 978-0-521-30312-5. Archivedfrom the original on 10 September 2017.
- hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
- ^ "Chapter 2: Bayer & E. Merck: Discovery and development of praziquantel*: Competing drugs for schistosomiasis treatment". International Strategies for Tropical Disease Treatments: Experiences with Praziquantel. EDM Research Series No. 026. WHO Essential Medicines. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
- PMID 23450530.
- ISBN 978-0-85369-342-0.
External links
- "Oxamniquine". Drugs.com. Archived from the original on 5 March 2016. Retrieved 23 January 2018.
- "Schistosomiasis treatment". Institute of Tropical Medicine. Antwerp. Archived from the original on 22 November 2004.