oxamniquine

Trade name: vansil

Small moleculeapproved

Approved

Jul 23, 1980

Oxamniquine 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 in man, 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. 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 to synthesis inhibition 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 — NCATS

Clinical trial activity

0 trials · 0 clinical orgs · 1 marketing orgs

Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Timeline

1980s

  1. Jul 23, 1980

    Pfizer — Earliest FDA Approval

  2. Jul 23, 1980

    Pfizer — NDA Organization

Indications

Mechanism of action

  • DNAINHIBITOR

    DNA inhibitor

Approval history

  • approvedPriority reviewJul 23, 1980

Chemistry & pharmacology

Loading structure…

SMILES

CC(C)NCC1CCC2=CC(CO)=C(C=C2N1)[N+]([O-])=O
Mol. weight
279.3348 g/mol
Lipinski Ro5
Pass
Rule of 3
Yes
Chirality
Racemic Mixture
Inorganic
No
Polymer
No
Availability
Discontinued

Oral

No

Parenteral

No

Topical

No

Sources

Also known as

  • mansil
  • mansil
  • oxamniquine
  • oxamniquine
  • oxamniquine
  • oxamniquine
  • oxamniquine
  • oxamniquine
  • oxamniquine
  • oxamniquine
  • oxamniquine
  • oxamniquine
  • oxamniquine
  • (+/-)-oxamniquine
  • uk-4271
  • uk-4271
  • uk-4271
  • vansil
  • vansil
  • vansil

Organizations

Marketing (2)

OrganizationOrg typeRelationshipDate
PfizerFor profitSYNJul 23, 1980
PfizerFor profitNDAJul 23, 1980