U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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

1981
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
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
[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
Name Type Language
OXAMNIQUINE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
NSC-352888
Code English
6-QUINOLINEMETHANOL, 1,2,3,4-TETRAHYDRO-2-(((1-METHYLETHYL)AMINO)METHYL)-7-NITRO-
Systematic Name English
oxamniquine [INN]
Common Name English
OXAMNIQUINE [HSDB]
Common Name English
UK-4271
Code English
1,2,3,4-Tetrahydro-2-[(isopropylamino)methyl]-7-nitro-6-quinolinemethanol
Systematic Name English
OXAMNIQUINUM [WHO-IP LATIN]
Common Name English
(±)-OXAMNIQUINE
Common Name English
OXAMNIQUINE [WHO-IP]
Common Name English
VANSIL
Brand Name English
OXAMNIQUINE [VANDF]
Common Name English
OXAMNIQUINE [MI]
Common Name English
Oxamniquine [WHO-DD]
Common Name English
OXAMNIQUINE [ORANGE BOOK]
Common Name English
OXAMNIQUINE [MART.]
Common Name English
MANSIL
Brand Name English
OXAMNIQUINE [USAN]
Common Name English
UK-4261
Code English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 6.1.3
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
WHO-VATC QP52AA02
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
WHO-ATC P02BA02
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
NDF-RT N0000175481
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
Code System Code Type Description
PUBCHEM
4612
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
NSC
352888
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
NCI_THESAURUS
C66258
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
EVMPD
SUB09494MIG
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
INN
3297
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
SMS_ID
100000083028
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
CHEBI
7819
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
HSDB
6510
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
DRUG CENTRAL
2009
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
WIKIPEDIA
OXAMNIQUINE
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
ECHA (EC/EINECS)
244-556-4
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
CAS
21738-42-1
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
ChEMBL
CHEMBL847
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID3023398
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
CAS
119623-12-0
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
SUPERSEDED
MERCK INDEX
m8288
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB01096
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
FDA UNII
0O977R722D
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
RXCUI
7778
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY RxNorm
MESH
D010073
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
OXAMNIQUINE
Created by admin on Fri Dec 15 16:26:13 GMT 2023 , Edited by admin on Fri Dec 15 16:26:13 GMT 2023
PRIMARY Description: A yellow-orange, crystalline powder. Solubility: Sparingly soluble in water, soluble in methanol R and acetone R. Category: Anti-schistosomal. Storage: Oxamniquine should be kept in a well-closed container. Definition: Oxamniquine contains not less than 97.0% and not more than 103.0% of C14H21N3O3, calculated with reference to theanhydrous substance.