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Oxamniquine

Catalog No. DB01096 Name DrugBank
CAS Number 21738-42-1 Website http://www.ualberta.ca/
M. F. C14H21N3O3 Telephone (780) 492-3111
M. W. 279.33484 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 967

SYNONYMS

IUPAC name
(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol
IUPAC Traditional name
oxamniquine
Brand Name
Vansil
Mansil

DATABASE IDS

CAS Number 21738-42-1
PubChem CID 4612
PubChem SID 46508789

PROPERTIES

Hydrophobicity(logP) 1.5
Solubility 820 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved
Description An anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine 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. (From Martidale, The Extra Pharmacopoeia, 31st ed, p121)
Indication For treatment of Schistosomiasis caused by Schistosoma mansoni
Pharmacology Oxamniquine is an anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine 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 egg.
Affected Organisms
Schistosoma mansoni
Biotransformation Probably hepatic
Absorption Well absorbed orally
Half Life 1-2.5 hours
References
Filho RP, de Souza Menezes CM, Pinto PL, Paula GA, Brandt CA, da Silveira MA: Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs. Bioorg Med Chem. 2007 Feb 1;15(3):1229-36. Epub 2006 Nov 16. [Pubmed]
See General references, Filho et. al. for synthesis of oxamniquine methacylate.
External Links
Wikipedia
Drugs.com

REFERENCES

  • Filho RP, de Souza Menezes CM, Pinto PL, Paula GA, Brandt CA, da Silveira MA: Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs. Bioorg Med Chem. 2007 Feb 1;15(3):1229-36. Epub 2006 Nov 16. PubmedSee General references, Filho et. al. for synthesis of oxamniquine methacylate.