Structure via PubChem · Public domain (PubChem)
oxamniquine
Sign in to saveAlso known as UK-4271, Vansil, Mansil
Oxamniquine, sold under the brand name Vansil among others, is a medication used to treat schistosomiasis due to Schistosoma mansoni. Praziquantel, however, is often the preferred treatment. It is given by mouth and used as a single dose.
Key facts
- Drug.ATC_suffix
- BA02
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 462266611
- Drug.IUPAC_name
- (RS)-1,2,3,4-Tetrahydro-2-isopropylaminomethyl-7-nitro-6-quinolylmethanol
- Drug.image
- Oxamniquine enantiomers labelled.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 300
- Drug.image2
- Oxamniquine enantiomers ball-and-stick models from xtal.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 300
- Drug.chirality
- Racemic mixture
- Drug.tradename
- Vansil
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- P02
- Drug.bioavailability
- Readily absorbed when taken by mouth
- Drug.metabolism
- Liver
- Drug.elimination_half life
- 1 to 2.5h
- Drug.excretion
- Kidney
via Wikipedia infobox
Chemical data
- Formula
- C14H21N3O3
- Molecular weight
- 279.33 g/mol
- IUPAC name
- [7-nitro-2-[(propan-2-ylamino)methyl]-1,2,3,4-tetrahydroquinolin-6-yl]methanol
- SMILES
- CC(C)NCC1CCC2=CC(=C(C=C2N1)[N+](=O)[O-])CO
- InChIKey
- XCGYUJZMCCFSRP-UHFFFAOYSA-N
- XLogP
- 2.2
- Polar surface area
- 90.1 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
548 papers- Oxamniquine derivatives overcome Praziquantel treatment limitations for Schistosomiasis.PLoS pathogens · 2023
- [Schistosomiasis].MMW Fortschritte der Medizin · 2017
- Medicinal chemistry of antischistosomal drugs: Praziquantel and oxamniquine.Bioorganic & medicinal chemistry · 2017
- Convulsions after oxamniquine.Transactions of the Royal Society of Tropical Medicine and Hygiene · 1987
- Schistosomiasis.Infectious disease clinics of North America · 1993
via PubMed
Wikidata facts
- Mass
- 279.158292
Show 4 more facts
- Commons category
- Oxamniquine
- chemical formula
- C₁₄H₂₁N₃O₃
- canonical SMILES
- CC(C)NCC1CCC2=CC(=C(C=C2N1)[N+](=O)[O-])CO
- defined daily dose
- 1
via Wikidata · CC0
~5 min read
Article
9 sectionsContents
- Medical uses
- Side effects
- Pharmacokinetics
- Mechanism of action
- History
- Brand names
- Stereochemistry
- References
- External links
Oxamniquine, sold under the brand name Vansil among others, is a medication used to treat schistosomiasis due to Schistosoma mansoni. Praziquantel, however, is often the preferred treatment. It is given by mouth and used as a single dose.
Common side effects include sleepiness, headache, nausea, diarrhea, and reddish urine. It is typically not recommended during pregnancy, if possible. Seizures may occur and therefore caution is recommended in people with epilepsy. It works by causing paralysis of the parasitic worms. It is in the anthelmintic family of medications.