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Aripiprazole lauroxil is a long acting injectable (LAI) pro-drug formulation of aripiprazole approved in the U.S. for the treatment of schizophrenia. Aripiprazole lauroxil is a dopamine D2 receptor partial antagonist, a 5-HT2A antagonist, and a 5- HT1A partial agonist that was developed by Alkermes. It was Aripiprazole lauroxil is a long acting injectable (LAI) pro-drug formulation of aripiprazole approved in the U.S. for the treatment of schizophrenia.28 Aripiprazole lauroxil is a dopamine D2 receptor partial antagonist, a 5-HT2A antagonist, and a 5- HT1A partial agonist that was developed by Alkermes. It was

Aripiprazole lauroxil, an N-acyloxymethyl proagent of Aripiprazole (HY-14546), is a Long-acting injectable (LAI) typical antipsychotic for schizophrenia and a ligand of dopamine receptor D2R/D4R. Aripiprazole lauroxil is cleaved by body’s enzyme esterase to N-hydroxymethyl aripiprazole (plus lauric acid) and then to aripiprazole (plus formaldehyde), no toxicity.

ChEBI: A dodecanoate ester obtained by formal condensation of the carboxy group of dodecanoic acid with the hydroxy group of 7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-2-oxo-3,4-dihydroquinolin-1(2H)-yl]methanol. A prodrug for aripipraz le, it is used for treatment of schizophrenia.

The synthesis of aripiprazole lauroxil has only been described on gram scale in the patent literature. Commercially available aripiprazole (58) was treated with formaldehyde to give hemiaminal 59 in 65% crude yield and was then heated with lauric anhydride to give aripiprazole lauroxil (VII) in 21% overall yield.

[1] Amani P,et al. Characterizing aripiprazole and its ester derivatives, lauroxil and cavoxil, in interaction with dopamine D2 receptor: Molecular docking and dynamics simulations with physicochemical appraisals[J]. Journal of Molecular Liquids, 2022, 362: 119787.
[2] Jann MW, et al. Long-Acting Injectable Second-Generation Antipsychotics: An Update and Comparison Between Agents.CNS Drugs. 2018 Mar;32(3):241-257. DOI:10.1007/s40263-018-0508-6
[3] Rohde M, et al. Biological conversion of aripiprazole lauroxil - An N-acyloxymethyl aripiprazole prodrug.Results Pharma Sci. 2014 May 2;4:19-25. DOI:10.1016/j.rinphs.2014.04.002