ArticleResults in pharma sciences2014
Biological conversion of aripiprazole lauroxil - An N-acyloxymethyl aripiprazole prodrug.
Article in Results in pharma sciences, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers, 1 of them a synthesis that pooled it.
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
12 citing papers in PubMed, 1 synthesis or guideline pooled it, 25 citations in OpenAlex.
- Long-Acting Injectable (LAI) Aripiprazole Formulations in the Treatment of Schizophrenia and Bipolar Disorder: a Systematic Review.Clinical drug investigation · 2019Pooled it
- Effect of Alkyl Chain Length on Physicochemical and Pharmacokinetic Performance of Aripiprazole Fatty Acid Prodrugs for Long-Acting Injectable Suspensions.Pharmaceutics · 2026Article
- Aripiprazole Lauroxil: Development and Evidence-Based Review of a Long-Acting Injectable Atypical Antipsychotic for the Treatment of Schizophrenia.Neuropsychiatric disease and treatment · 2025Review
- An Injectable Oil-Based Depot Formulation ofPharmaceutics · 2024Article
- Synthetic Approaches to Piperazine-Containing Drugs Approved by FDA in the Period of 2011-2023.Molecules (Basel, Switzerland) · 2023Review
- Aripiprazole Plasma Concentrations Delivered from Two 2-Month Long-Acting Injectable Formulations: An Indirect Comparison.Neuropsychiatric disease and treatment · 2023Article
- Aripiprazole Lauroxil, a Novel Injectable Long-Acting Antipsychotic Treatment for Adults with Schizophrenia: A Comprehensive Review.Neurology international · 2021Review
- The expanding role of prodrugs in contemporary drug design and development.Nature reviews. Drug discovery · 2018Review
- Long-Acting Injectable Second-Generation Antipsychotics: An Update and Comparison Between Agents.CNS drugs · 2018Review
- Review
- Pharmacogenetic evaluation to assess breakthrough psychosis with aripiprazole long-acting injection: a case report.BMC psychiatry · 2017Article
- Plasma concentrations and dosing of 2 long-acting injectable formulations of aripiprazole.Neuropsychiatric disease and treatment · 2017Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
8 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
N-acyloxyalkylation of NH-acidic compounds can be a prodrug approach for e.g. tertiary or some N-heterocyclic amines and secondary amides and have the potential to modify the properties of the parent drug for specific uses, for example its physicochemical, pharmacokinetic or biopharmaceutical properties. Aripiprazole lauroxil was prepared as a model compound for such prodrugs and its bioconversion was investigated both in vitro and in vivo. Theoretically, N-acyloxyalkyl derivates of NH-acid compounds undergo a two-step bioconversion into the parent NH-acidic drug through an N-hydroxyalkyl intermediate. However, to our knowledge no published studies have investigated the formation of an intermediate in vivo. In the present study, it was demonstrated that the assumed N-hydroxymethyl intermediate was readily observed both in vitro and in vivo. In vivo, the observed plasma concentration of the intermediate was at the same level as the drug (aripiprazole). When prodrug intermediates are formed, it is important to make a proper pharmacological, pharmacokinetic and toxicological evaluation of the intermediates to ensure patient safety; however, several challenges were identified when testing an N-acyloxyalkyl prodrug. These included the development of a suitable bioanalytical method, the accurate prediction of prodrug bioconversion and thereby the related pharmacokinetics in humans and the toxicological potential of the intermediate.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.