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Purity: ≥98%
Toloxatone, aslo known as MD 69276, is an antidepressant launched in 1984 in France for the treatment of depression. It acts as a selective reversible inhibitor of MAO-A (RIMA). Toloxatone is a reversible monoamine oxidase A inhibitor (MAOI) and antidepressant. Toloxatone belongs to the aryloxazolidinones, a relatively new class of reversible monoamine oxidase A inhibitors (MAOI References: Baek SC, Kang MG, Park JE, Lee JP, Lee H, Ryu HW, Park CM, Park D, Cho ML, Oh SR, Kim H. Osthenol, a prenylated coumarin, as a monoamine oxidase A inhibitor with high selectivity. Bioorg Med Chem Lett. 2019 Mar 15;29(6):839-843. doi: 10.1016/j.bmcl.2019.01.016. Epub 2019 Jan 18. PubMed PMID: 30686752.
| Targets |
Monoamine oxidase A (MAO-A) [1]
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|---|---|
| ln Vitro |
Enzyme inhibition: Toloxatone demonstrated reversible inhibition of MAO-A through direct interaction with the enzyme's flavin adenine dinucleotide (FAD) cofactor. Spectrophotometric studies showed dose-dependent suppression of MAO-A activity, with a binding affinity characterized by molecular orbital calculations [1].
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| Enzyme Assay |
- Spectrophotometric MAO-A inhibition assay: Recombinant MAO-A was incubated with kynuramine as a substrate. Toloxatone was added at concentrations ranging from 1 μM to 1 mM, and enzyme activity was monitored by measuring the formation of benzaldehyde via absorbance at 340 nm. The reaction was carried out in phosphate buffer (pH 7.4) at 37°C. Kinetic analysis confirmed reversible inhibition kinetics [1].
- FAD binding study: UV-visible spectroscopy was used to analyze the interaction between Toloxatone and FAD. The drug was titrated into a solution of FAD, and changes in absorption spectra were recorded. Molecular orbital calculations (AM1 method) were performed to model the binding mode, indicating hydrogen bonding and π-π stacking interactions [1]. |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Mainly hepatic 1% of drug is excreted unchanged in the urine High hepatic excretion rate Biological Half-Life 1-3 h |
| Toxicity/Toxicokinetics |
34521 rat LD50 oral 1225 mg/kg BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX); BEHAVIORAL: COMA; LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Drugs of the Future., 1(569), 1976
34521 mouse LD50 oral 1300 mg/kg BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX); BEHAVIORAL: COMA; LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Drugs of the Future., 1(569), 1976 34521 mouse LD50 intraperitoneal 650 mg/kg BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX); BEHAVIORAL: COMA; LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Drugs of the Future., 1(569), 1976 |
| References |
[1]. A reversible monoamine oxidase inhibitor, toloxatone: spectrophotometric and molecular orbital studies of the interaction with flavin adenine dinucleotide (FAD). European Journal of Medicinal Chemistry. 1994, 29(4):269-277.
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| Additional Infomation |
5-(hydroxymethyl)-3-(3-methylphenyl)-1,3-oxazolidin-2-one is a member of the class of oxazolidinones that is 5-(hydroxymethyl)-1,3-oxazolidin-2-one substituted by a 3-methylphenyl group at position 3. It is a member of toluenes, an oxazolidinone and a primary alcohol.
Toloxatone is an antidepressant agent, the first ever use of which was in France, 1984. It acts as a selective and reversible inhibitor of monoamine oxidase-A (MOA). Drug Indication For the treatment of major depressive disorder. Mechanism of Action This medication is a reversible inhibitor of monoamine oxidase type-A (also known as RIMA). MAO-A can be found in norepinephrinergic and serotonergic neurons and regulates the metabolism of serotonin and catecholamines, allowing for increased circulation in the synaptic cleft. Traditional monoamine oxidase inhibitors irreversibly inhibit monoamine oxidase and therefore, side effects, drug interactions, and food interactions persist as long as 2-3 weeks after discontinuing toloxatone. The elevation of serotonin and norepinephrine levels occurs rapidly after medication administration. However, the therapeutic relief of depressive symptoms requires weeks of daily treatment to observe results. Selective and reversible MAO-A inhibitors are more effective in treating major depression without several of the drug and food interactions associated with traditional monoamine oxidase inhibitors. Pharmacodynamics This drug has been shown to help manage the symptoms of depression by maintaining neuro-synaptic levels of serotonin and catecholamines while regulating their metabolism, which leads to relief of depressive symptoms. - Mechanism of action: Toloxatone acts as a reversible MAO-A inhibitor by binding to the FAD cofactor, blocking the enzyme's active site. This prevents oxidation of monoamine neurotransmitters (e.g., serotonin, norepinephrine), increasing their synaptic availability [1]. - Pharmacological classification: Classified as a reversible inhibitor of monoamine oxidase A (RIMA), Toloxatone is used as an antidepressant with a lower risk of hypertensive crises compared to irreversible MAO inhibitors [1]. |
| Molecular Formula |
C11H13NO3
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|---|---|
| Molecular Weight |
207.229
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| Exact Mass |
207.09
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| Elemental Analysis |
C, 63.76; H, 6.32; N, 6.76; O, 23.16
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| CAS # |
29218-27-7
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| Related CAS # |
29218-27-7;
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| PubChem CID |
34521
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| Appearance |
White to off-white solid powder
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| Density |
1.245g/cm3
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| Boiling Point |
358.9ºC at 760mmHg
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| Melting Point |
76°
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| Flash Point |
170.9ºC
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| Vapour Pressure |
8.9E-06mmHg at 25°C
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| Index of Refraction |
1.57
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| LogP |
1.377
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
15
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| Complexity |
244
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=CC(=CC=C1)N2CC(OC2=O)CO
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| InChi Key |
MXUNKHLAEDCYJL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H13NO3/c1-8-3-2-4-9(5-8)12-6-10(7-13)15-11(12)14/h2-5,10,13H,6-7H2,1H3
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| Chemical Name |
5-(Hydroxymethyl)-3-(3-methylphenyl)-2-oxazolidinone
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| Synonyms |
MD 69276; MD-69276; Toloxatone; 29218-27-7; Humoryl; Perenum; Toloxatona; Toloxatonum; Taloxotone; Delalande 69,276; MD69276; Toloxatone; Humoryl Delalande 69276; Perenum.
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~603.19 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (10.04 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (10.04 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (10.04 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8256 mL | 24.1278 mL | 48.2556 mL | |
| 5 mM | 0.9651 mL | 4.8256 mL | 9.6511 mL | |
| 10 mM | 0.4826 mL | 2.4128 mL | 4.8256 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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