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Last update 08 May 2025

Toloxatone

Last update 08 May 2025

Overview

R&D Status

Clinical Result

Translational Medicine

Overview

Basic Info

Drug Type

Small molecule drug

Synonyms

Toloxatone (INN), Humoryl

+ [2]

Target

MAO-A

Action

inhibitors

Mechanism

MAO-A inhibitors(Monoamine oxidase A inhibitors)

Therapeutic Areas

Other Diseases

Active Indication

Depressive Disorder

Inactive Indication-

Originator Organization-

Active Organization-

Inactive Organization-

License Organization-

Drug Highest PhaseApproved

First Approval Date

France (01 Jan 1984),

Depressive Disorder

Regulation-

Structure/Sequence

Molecular FormulaC11H13NO3

InChIKeyMXUNKHLAEDCYJL-UHFFFAOYSA-N

CAS Registry29218-27-7

100 Clinical Results associated with Toloxatone

100 Translational Medicine associated with Toloxatone

100 Patents (Medical) associated with Toloxatone

159

Literatures (Medical) associated with Toloxatone

01 Apr 2025·Bioorganic & Medicinal Chemistry

New phenylpiperazine-thiazolidine-2,4-dione hybrids targeting MAO inhibition: Synthesis, biological evaluation, kinetic study and in silico insights

Article

Author: El-Halaby, Lamiaa O ; Elgazar, Abdullah A ; Tawfik, Samar S ; Ewes, Wafaa A ; Al-Sanea, Mohammad M ; Hamdi, Abdelrahman

Monoamine oxidase inhibitors are promising drug targets for many neurological diseases such as depression, Alzheimer's disease, and Parkinson's disease. The current study developed new hybrid compounds by merging phenyl piperazines, and 2,4-thiazolidinedione moieties based on their reported MAO inhibitory activities. The newly synthesized derivatives were screened for their MAOs inhibitory activity using in-vitro fluorometric assay. Most newly synthesized compounds elicited strong inhibitory activity against both hMAO isozymes. Hybrids 4a and 4c were the most potent hMAO-A inhibitors with IC₅₀ values of 0.194 and 0.188 µM, respectively, compared to toloxatone as reference (IC₅₀ = 1.080 µM), meanwhile, compound 4g exhibited the most potent inhibitory activity against MAO-B with an IC₅₀ value of 0.330 µM. The kinetic study of compound 4c revealed that it exhibited a mixed inhibition mode with a K_i value of 3.4 nM. Compound 4c was evaluated against the normal SH-SY5Y cell line and found to be non-cytotoxic at its active inhibition concentration. ADME profiles of the most active hybrids 4a, 4c, 4j, and 4k revealed that they could serve as successful drug candidates showing good CNS penetration. Molecular docking simulations were executed for the most active motifs 4a and 4c to demonstrate the binding pattern with the target proteins explaining their potential inhibitory activity. Lastly, this study will significantly contribute to developing novel safe, effective medications for treating various neurological disorders in the foreseeable future.

07 Feb 2025·Organic Letters

Synthesis of N-Aryl Carbamates from Aryl(TMP)iodonium Salts via C–N Coupling

Article

Author: Hatton, Joseph ; Stuart, David R.

Modular C-N coupling is a desirable way to construct N-aryl carbamates, which are privileged scaffolds in active pharmaceutical ingredients. However, there are no broadly applicable metal-free methods for theN-arylation of carbamates. Herein, we describe a metal-free approach that uses aryl(TMP)iodonium salts as arylation reagents for cyclic carbamates by exploiting the metal-like reactivity of iodine(III). The scope includes 25 examples, including 17 different aryl(TMP)iodonium salts and 9 different carbamates, in yields ranging between 55 and 97% (75% avg).

06 Sep 2024·Organic Letters

Molecular Editing of Toluene by Sequential meta-C–H/Benzylic C–N Deaminative Functionalizations

Article

Author: Jin, Zhong ; Yan, Yifei ; Xu, Xiaohua ; Liu, Zelin ; He, Siquan ; Jiang, Zhiwei

An approach to synthesizing structurally diverse toluene derivatives via sequential meta-C-H and benzylic C-N deaminative functionalization was developed by using a recyclable bifunctional directing template. The functionalized Katritzky salt intermediates are shown to be engaged in a wide range of carbon-carbon and carbon-heteroatom bond formation reactions. The synthetic utility of the strategy was demonstrated by late-stage functionalization of toloxatone.

100 Deals associated with Toloxatone

External Link

KEGG	Wiki	ATC	Drug Bank
D02559	Toloxatone	N06AG03	DB09245

R&D Status

10 top approved records.

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Indication	Country/Location	Organization	Date
Depressive Disorder	France	-	01 Jan 1984

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