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Details

Stereochemistry RACEMIC
Molecular Formula C14H21N3O3
Molecular Weight 279.3348
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXAMNIQUINE

SMILES

CC(C)NCC1CCC2=C(N1)C=C(C(CO)=C2)[N+]([O-])=O

InChI

InChIKey=XCGYUJZMCCFSRP-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C14H21N3O3
Molecular Weight 279.3348
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
VANSIL

Cmax

ValueDoseCo-administeredAnalytePopulation
1983 ng/mL
1 g single, oral
OXAMNIQUINE plasma
Homo sapiens
1267 ng/mL
1 g single, oral
OXAMNIQUINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
417900 ng × min/mL
1 g single, oral
OXAMNIQUINE plasma
Homo sapiens
339097 ng × min/mL
1 g single, oral
OXAMNIQUINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
111 min
1 g single, oral
OXAMNIQUINE plasma
Homo sapiens
151.2 min
1 g single, oral
OXAMNIQUINE plasma
Homo sapiens

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
15 mg/kg body weight twice daily for 1 day in adults. Doses 20 or 40 mg/kg per day have been used in children in Africa.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
0O977R722D
Record Status Validated (UNII)
Record Version