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
SMILES
CC(C)NCC1CCC2=CC(CO)=C(C=C2N1)[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
| 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 | ( + / - ) |
DescriptionSources: http://www.drugs.com/mtm/vansil.htmlCurator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB01096
https://en.wikipedia.org/wiki/Oxamniquine
Sources: http://www.drugs.com/mtm/vansil.html
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=4626859
Curator's Comment: Oxamniquine was first described by Kaye and Woolhouse in 1972 as a metabolite of the compound UK 3883
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2366043 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=2617584 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | VANSIL Approved UseUnknown Launch Date1981 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1983 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3104279 |
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 |
|
1267 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3104279 |
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 |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
417900 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3104279 |
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 |
|
339097 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3104279 |
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
111 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3104279 |
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 |
|
151.2 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3104279 |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs. | 2007-02-01 |
|
| Preliminary investigations of some derivatives of oxamniquine. | 1995-04 |
|
| [Cardiac arrhythmia with oral oxamniquine use in the schistosomiasis mansoni treatment]. | 1993-11-01 |
|
| Convulsions after oxamniquine. | 1987 |
|
| A review of clinical experience with oxamniquine. | 1987 |
|
| Seizures associated with oxamniquine therapy. | 1986-03 |
|
| [Neurotoxicity of oxamniquine in the treatment of human Schistosoma mansoni infection]. | 1985-05-01 |
|
| Seizures and electroencephalograph changes associated with oxamniquine therapy. | 1978-03 |
|
| Field trials with oxamniquine in a Schistosomiasis mansoni-endemic area. | 1977-03 |
|
| Long-term hepatocellular effects of hycanthone and of two other anti-Schistosomal drugs in mice infected with Schistosoma mansoni. | 1976-06 |
Patents
| Substance Class |
Chemical
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C250
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WHO-ESSENTIAL MEDICINES LIST |
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QP52AA02
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P02BA02
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DB01096
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D010073
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OXAMNIQUINE
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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. |
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