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Oxamniquine information


Oxamniquine
Clinical data
Trade namesVansil
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
By mouth
ATC code
  • P02BA02 (WHO) QP52AA02 (WHO)
Pharmacokinetic data
BioavailabilityReadily absorbed when taken by mouth
MetabolismLiver
Elimination half-life1 to 2.5h
ExcretionKidney
Identifiers
IUPAC name
  • (RS)-1,2,3,4-Tetrahydro-2-isopropylaminomethyl-7-nitro-6-quinolylmethanol
CAS Number
  • 21738-42-1 checkY
PubChem CID
  • 4612
DrugBank
  • DB01096 checkY
ChemSpider
  • 4451 checkY
UNII
  • 0O977R722D
KEGG
  • D00460 checkY
ChEBI
  • CHEBI:7819 ☒N
ChEMBL
  • ChEMBL847 checkY
PDB ligand
  • OAQ (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID3023398 Edit this at Wikidata
ECHA InfoCard100.040.491 Edit this at Wikidata
Chemical and physical data
FormulaC14H21N3O3
Molar mass279.340 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
SMILES
  • CC(C)NCC1CCC2=CC(=C(C=C2N1)[N+](=O)[O-])CO
InChI
  • InChI=1S/C14H21N3O3/c1-9(2)15-7-12-4-3-10-5-11(8-18)14(17(19)20)6-13(10)16-12/h5-6,9,12,15-16,18H,3-4,7-8H2,1-2H3 checkY
  • Key:XCGYUJZMCCFSRP-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

  1. ^ a b c d World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 94. hdl:10665/44053. ISBN 978-9-2415-4765-9.
  2. ^ a b Fenwick A, Utzinger J (2010). "Helminthic Diseases: Schistosomiasis". In Griffiths J, Maguire JH, Heggenhougen K, Quah SR (eds.). Public Health and Infectious Diseases. Elsevier. p. 351. ISBN 978-0-12-381507-1. Archived from the original on 20 December 2016.
  3. ^ Kuhlmann FM, Fleckenstein JM (2016). "Antiparasitic Agents". In Cohen J, Powderly WG, Opal SM (eds.). Infectious Diseases (4th ed.). Elsevier Health Sciences. p. 1371. ISBN 978-0-7020-6338-1. Archived from the original on 20 December 2016.
  4. ^ a b "Oxamniquine medical facts from Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
  5. ^ Jordan P (1985). "Drug Trials: Oxamniquine". Schistosomiasis: The St Lucia Project. CUP Archive. p. 298. ISBN 978-0-521-30312-5. Archived from the original on 10 September 2017.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. ^ "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.

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Oxamniquine

Last Update:

Oxamniquine, sold under the brand name Vansil among others, is a medication used to treat schistosomiasis due to Schistosoma mansoni. Praziquantel, however...

Word Count : 982

Anthelmintic

Last Update:

and also possesses antiprotozoal effects. This is also an ascaricide. Oxamniquine – effective against flatworms (e.g., tapeworms and schistosoma) Praziquantel...

Word Count : 1918

WHO Model List of Essential Medicines

Last Update:

Trihexyphenidyl is an alternative benserazide is an alternative for carbidopa Oxamniquine is listed for use when praziquantel treatment fails. > 1 month. Only...

Word Count : 4835

Schistosomiasis

Last Update:

encephalitis related to vasculitis, myocarditis, or pulmonary events. Oxamniquine (50 mg/kg once) can be administer at the early phase of schistosomiasis...

Word Count : 10040

Moxidectin

Last Update:

acid Metrifonate‡ Other/unknown quinoline Arpraziquantel Praziquantel# Oxamniquine# phenol Bithionol thiazole Niridazole thioxanthone Hycanthone Lucanthone...

Word Count : 1200

Tetrahydroquinoline

Last Update:

derivatives of tetrahydroquinoline are common in medicinal chemistry. Oxamniquine, dynemycin, viratmycin, and nicainoprol are bioactive tetrahydroquinolines...

Word Count : 216

Helminthiasis

Last Update:

schistosomiasis, taeniasis, and most types of food-borne trematodiases. Oxamniquine is also widely used in mass deworming programmes. Pyrantel is commonly...

Word Count : 5247

Schistosoma mansoni

Last Update:

drug for S. mansoni infection is praziquantel at a dose of 40 mg/kg. Oxamniquine is also used. As of 2021, 251.4 million people worldwide are having schistosomiasis...

Word Count : 6881

Schistosomiasis vaccine

Last Update:

from the infection. While chemotherapeutic drugs, such as praziquantel, oxamniquine and metrifonate both no longer on the market, are currently considered...

Word Count : 707

List of drugs used to treat schistosomiasis

Last Update:

chloroxylenol hycanthone lucanthone metrifonate niridazole oltipraz oxamniquine praziquantel stibophen Schistosomiasis vaccine Schistosomicides at the...

Word Count : 110

Pfizer UK

Last Update:

outstanding contribution made to tropical medicine by the medicine Mansil (oxamniquine), which had been developed at the Sandwich site. Feldene (piroxicam)...

Word Count : 1435

WHO Model List of Essential Medicines for Children

Last Update:

developmental disorders in children exposed to valproate in the womb. Oxamniquine is listed for use when praziquantel treatment fails. > 1 month. Only...

Word Count : 2501

ATCvet code QP52

Last Update:

list, which follows the WHO version. QP52AA01 Praziquantel QP52AA02 Oxamniquine QP52AA04 Epsiprantel QP52AA30 Combinations of quinoline derivatives and...

Word Count : 272

ATC code P02

Last Update:

this list, which follows the WHO version. P02BA01 Praziquantel P02BA02 Oxamniquine P02BA03 Arpraziquantel P02BB01 Metrifonate P02BX01 Bithionol P02BX02...

Word Count : 185

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