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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

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
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
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 UTC 2023 , Edited by admin on Fri Dec 15 16:26:13 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.1.3
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WHO-VATC QP52AA02
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WHO-ATC P02BA02
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NDF-RT N0000175481
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Code System Code Type Description
PUBCHEM
4612
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PRIMARY
NSC
352888
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PRIMARY
NCI_THESAURUS
C66258
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PRIMARY
EVMPD
SUB09494MIG
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PRIMARY
INN
3297
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PRIMARY
SMS_ID
100000083028
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PRIMARY
CHEBI
7819
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PRIMARY
HSDB
6510
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PRIMARY
DRUG CENTRAL
2009
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PRIMARY
WIKIPEDIA
OXAMNIQUINE
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PRIMARY
ECHA (EC/EINECS)
244-556-4
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PRIMARY
CAS
21738-42-1
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PRIMARY
ChEMBL
CHEMBL847
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PRIMARY
EPA CompTox
DTXSID3023398
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PRIMARY
CAS
119623-12-0
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SUPERSEDED
MERCK INDEX
m8288
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PRIMARY Merck Index
DRUG BANK
DB01096
Created by admin on Fri Dec 15 16:26:13 UTC 2023 , Edited by admin on Fri Dec 15 16:26:13 UTC 2023
PRIMARY
FDA UNII
0O977R722D
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PRIMARY
RXCUI
7778
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PRIMARY RxNorm
MESH
D010073
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
OXAMNIQUINE
Created by admin on Fri Dec 15 16:26:13 UTC 2023 , Edited by admin on Fri Dec 15 16:26:13 UTC 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.