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Details

Stereochemistry UNKNOWN
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
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: http://www.drugbank.ca/drugs/DB01096 https://en.wikipedia.org/wiki/Oxamniquine

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

Curator's Comment: Oxamniquine was first described by Kaye and Woolhouse in 1972 as a metabolite of the compound UK 3883

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
VANSIL

Approved Use

Unknown

Launch Date

3.74111994E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1267 ng/mL
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
OXAMNIQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1983 ng/mL
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
OXAMNIQUINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
339097 ng × min/mL
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
OXAMNIQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
417900 ng × min/mL
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
OXAMNIQUINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
151.2 min
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
OXAMNIQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
111 min
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
OXAMNIQUINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
PubMed

PubMed

TitleDatePubMed
Long-term hepatocellular effects of hycanthone and of two other anti-Schistosomal drugs in mice infected with Schistosoma mansoni.
1976 Jun
Field trials with oxamniquine in a Schistosomiasis mansoni-endemic area.
1977 Mar
Seizures and electroencephalograph changes associated with oxamniquine therapy.
1978 Mar
[Neurotoxicity of oxamniquine in the treatment of human Schistosoma mansoni infection].
1985 May-Jun
Seizures associated with oxamniquine therapy.
1986 Mar
Convulsions after oxamniquine.
1987
A review of clinical experience with oxamniquine.
1987
[Cardiac arrhythmia with oral oxamniquine use in the schistosomiasis mansoni treatment].
1993 Nov-Dec
Preliminary investigations of some derivatives of oxamniquine.
1995 Apr
Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs.
2007 Feb 1
Patents

Patents

Sample Use Guides

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
Created
by admin
on Sat Dec 16 10:13:26 UTC 2023
Edited
by admin
on Sat Dec 16 10:13:26 UTC 2023
Record UNII
00BCY677OT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXAMNIQUINE, (-)-
Common Name English
6-QUINOLINEMETHANOL, 1,2,3,4-TETRAHYDRO-2-(((1-METHYLETHYL)AMINO)METHYL)-7-NITRO-, (-)-
Systematic Name English
Code System Code Type Description
FDA UNII
00BCY677OT
Created by admin on Sat Dec 16 10:13:26 UTC 2023 , Edited by admin on Sat Dec 16 10:13:26 UTC 2023
PRIMARY
PUBCHEM
4612
Created by admin on Sat Dec 16 10:13:26 UTC 2023 , Edited by admin on Sat Dec 16 10:13:26 UTC 2023
PRIMARY
CAS
119678-90-9
Created by admin on Sat Dec 16 10:13:26 UTC 2023 , Edited by admin on Sat Dec 16 10:13:26 UTC 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER