Oxaniquine is a medication that effectively treats schistosomiasis [1].

When compared to controls, the death rate of infected snails was lowered by oxaniquine (500 mg/kg) either by itself or in combination with praziquantel [1].

Absorption, Distribution and Excretion
Oral absorption is good. Oxanibrine and its metabolites are primarily excreted in the urine. Approximately 40-75% of the oral dose is excreted in the urine within 24 hours after administration, mainly as a 6-carboxylic acid metabolite. Approximately 0.5-2% of the oral dose is excreted unchanged in the urine; less than 1% is excreted as a 2-carboxylic acid metabolite. Oxanibrine is well absorbed after oral administration. Food can decrease the rate and extent of absorption in the gastrointestinal tract. Peak plasma concentrations of oxanibrine occur approximately 1-3 hours after the usual oral dose. …Differences in plasma oxanibrine concentrations among patients may be due to biodegradation of the drug in the gastrointestinal mucosa during absorption. …Oxanibrine undergoes extensive first-pass metabolism in the gastrointestinal lumen and/or in the gastrointestinal mucosa before and/or during absorption in animals. In one study, after a single oral dose of 15 mg/kg oxaniquine in adults and children infected with Schistosoma mansoni, peak serum drug concentrations reached 70–2595 ng/ml and 89–1500 ng/ml, respectively, within 1.5–3 hours. In another study, after a single oral dose of 1 g oxaniquine in patients with advanced hepatosplenic schistosomiasis and healthy adults, mean peak plasma drug concentrations were reached at approximately 1.7 hours and 1.4 hours, respectively, at 1267 ng/ml and 1983 ng/ml. Metabolites/Metabolites Possibly metabolized in the liver. The drug is extensively metabolized primarily in the gastrointestinal mucosa and/or intestinal lumen, via enzymatic oxidation of 6-hydroxymethyl to produce a 6-carboxylic acid metabolite. Trace amounts of the 2-carboxylic acid metabolite have also been observed in urine, reflecting the oxidation of the side chain. These metabolites do not possess antiheme body activity.

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Biological half-life
1-2.5 hours
The plasma half-life of oxaniquine is approximately 1-2.5 hours.

[1]. Mattos AC, et al. Evaluation of the effect of oxamniquine, praziquantel and a combination of both drugs on the intramolluscan phase of Schistosoma mansoni. Acta Trop. 2007 May;102(2):84-91.

{2-[(isopropylamino)methyl]-7-nitro-1,2,3,4-tetrahydroquinoline-6-yl}methanol belongs to the quinoline class of compounds. Its structure is 1,2,3,4-tetrahydroquinoline, with (isopropylamino)methyl, hydroxymethyl, and nitro groups substituted at positions 2, 6, and 7, respectively. It belongs to the quinoline class, C-nitro compounds, secondary amino compounds, and aromatic primary alcohols. Oxaniquin is an anthelmintic with activity against Schistosoma mansoni, but ineffective against other Schistosoma genera. Oxaniquin causes the parasite to migrate from the mesenteric vein to the liver; males remain in the liver, while females return to the mesentery but are unable to lay eggs. (Excerpt from Martindale: Pharmacopoeia, 31st edition, p. 121) Oxaniquin is an anthelmintic. It is an anthelmintic with activity against Schistosoma mansoni, but ineffective against other Schistosoma genera. Oxaniquine causes the parasite to migrate from the mesenteric vein to the liver, where males remain; females return to the mesentery but are unable to lay eggs. (Excerpt from Martindale Pharmacopoeia, 31st edition, p. 121)

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Indications
For the treatment of schistosomiasis caused by Schistosoma mansoni

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Mechanism of Action
Oxaniquine may be related to the irreversible inhibition of the parasite's nucleic acid metabolism. One hypothesis suggests that activation of the drug requires only one step: schistosome sulfotransferase converts oxaniquine into an ester (possibly acetate, phosphate, or sulfate). Subsequently, the ester spontaneously dissociates, and the resulting electrophilic reactant alkylates the schistosome's DNA.
This causes the parasite to detach from its usual mesenteric vein, enter the liver, remain there, and ultimately be killed by host tissue responses (such as phagocytosis). Worm detachment appears to originate primarily from muscle contraction and paralysis, followed by fixation of the suckers, allowing the worm to detach from the blood vessel wall and be passively expelled by normal blood flow. Schistosomas sensitive and resistant to hemonconazole (and also sensitive and resistant to oxaniquine) were exposed in vitro to tritium-labeled oxaniquine. Initial drug absorption was substantially similar in both species. Homogenized worms incubated with tritium-labeled oxaniquine were fractionated, and purified DNA fractions were obtained by ethanol precipitation, RNase and protease digestion, repeated phenol-chloroform extraction, cesium chloride gradient centrifugation, and thorough dialysis. Radiolabeled oxaniquine was detected in DNA fragments from sensitive schistosomes at a concentration of approximately one drug molecule per 50,000 base pairs, while almost no drug was found in DNA fragments from resistant schistosomes. These results support the hypothesis that oxaniquine, similar to hemonconazole, exerts its effects by alkylating the large molecules of sensitive schistosomes.

C14H21N3O3

279.33484

279.158

21738-42-1

4612

Pale yellow crystals from isopropanol
Yellow-orange, crystalline solid

1.174g/cm3

443.6ºC at 760mmHg

147-149ºC

222.1ºC

1.19E-08mmHg at 25°C

1.56

2.863

3

5

4

20

332

0

CC(C)NCC1CCC2=CC(=C(C=C2N1)[N+](=O)[O-])CO

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)