Aripiprazole lauroxil

Aripiprazole lauroxil
Clinical data
Trade names	Aristada, Aristada Initio
Other names	N-Lauroyloxymethylaripiprazole; ALKS-9070; ALKS-9072; RDC-3317; Dodecanoic acid-[7-[4-[4-(2,3-dichlorophenyl)-1-piperazinyl]butoxy]-3,4-dihydro-2-oxo-1(2H)-quinolinyl]methyl ester
AHFS/Drugs.com	Monograph
MedlinePlus	a615048
Pregnancy; category	AU: C; ;
Routes of; administration	Intramuscular
ATC code	None;
Legal status
Legal status	US: WARNINGRx-only;
Identifiers
	IUPAC name [7-[4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butoxy]-2-oxo-3,4-dihydroquinolin-1-yl]methyl dodecanoate;
CAS Number	1259305-29-7;
PubChem CID	49831411;
DrugBank	DB14185;
ChemSpider	28651973;
UNII	B786J7A343;
KEGG	D10364;
ChEBI	CHEBI:90930;
ChEMBL	ChEMBL2219425;
CompTox Dashboard (EPA)	DTXSID60154997 ;
ECHA InfoCard	100.261.570
Chemical and physical data
Formula	C36H51Cl2N3O4
Molar mass	660.72 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCCCCCCC(=O)OCN1C(=O)CCC2=C1C=C(C=C2)OCCCCN3CCN(CC3)C4=C(C(=CC=C4)Cl)Cl;
	InChI InChI=1S/C36H51Cl2N3O4/c1-2-3-4-5-6-7-8-9-10-16-35(43)45-28-41-33-27-30(19-17-29(33)18-20-34(41)42)44-26-12-11-21-39-22-24-40(25-23-39)32-15-13-14-31(37)36(32)38/h13-15,17,19,27H,2-12,16,18,20-26,28H2,1H3; Key:DDINXHAORAAYAD-UHFFFAOYSA-N;

Aripiprazole lauroxil, sold under the brand name Aristada, is a long-acting injectable atypical antipsychotic that was developed by Alkermes.^[3]^[4]^[5] It is an N-acyloxymethyl prodrug of aripiprazole that is administered via intramuscular injection once every four to eight weeks for the treatment of schizophrenia.^[3]^[4]^[5] Aripiprazole lauroxil was approved by the U.S. Food and Drug Administration (FDA) on 5 October 2015.^[6]^[7]

^ ^a ^b "Aripiprazole Use During Pregnancy". Drugs.com. 5 February 2020. Retrieved 29 August 2020.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ ^a ^b Rohde M, M Rk N, Håkansson AE, Jensen KG, Pedersen H, Dige T, J Rgensen EB, Holm R (2014). "Biological conversion of aripiprazole lauroxil - An N-acyloxymethyl aripiprazole prodrug". Results Pharma Sci. 4: 19–25. doi:10.1016/j.rinphs.2014.04.002. PMC 4050360. PMID 25756003.
^ ^a ^b Turncliff R, Hard M, Du Y, Risinger R, Ehrich EW (2014). "Relative bioavailability and safety of aripiprazole lauroxil, a novel once-monthly, long-acting injectable atypical antipsychotic, following deltoid and gluteal administration in adult subjects with schizophrenia". Schizophr. Res. 159 (2–3): 404–10. doi:10.1016/j.schres.2014.09.021. PMID 25266547. S2CID 1036686.
^ ^a ^b Meltzer HY, Risinger R, Nasrallah HA, Du Y, Zummo J, Corey L, Bose A, Stankovic S, Silverman BL, Ehrich EW (2015). "A randomized, double-blind, placebo-controlled trial of aripiprazole lauroxil in acute exacerbation of schizophrenia". J Clin Psychiatry. 76 (8): 1085–90. doi:10.4088/JCP.14m09741. PMID 26114240.
^ Citrome L (2015). "Aripiprazole Long-Acting Injectable Formulations for Schizophrenia: Aripiprazole Monohydrate and Aripiprazole Lauroxil". Expert Rev Clin Pharmacol. 9 (2): 169–86. doi:10.1586/17512433.2016.1121809. PMID 26573020. S2CID 207208248.
^ "Aristada (Aripiprazole lauroxil) FDA Approval History".

[Drugs.com_pregnancy-1] "Aripiprazole Use During Pregnancy". Drugs.com. 5 February 2020. Retrieved 29 August 2020.

[FDA-AllBoxedWarnings-2] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[pmid25756003-3] Rohde M, M Rk N, Håkansson AE, Jensen KG, Pedersen H, Dige T, J Rgensen EB, Holm R (2014). "Biological conversion of aripiprazole lauroxil - An N-acyloxymethyl aripiprazole prodrug". Results Pharma Sci. 4: 19–25. doi:10.1016/j.rinphs.2014.04.002. PMC 4050360. PMID 25756003.

[pmid25266547-4] Turncliff R, Hard M, Du Y, Risinger R, Ehrich EW (2014). "Relative bioavailability and safety of aripiprazole lauroxil, a novel once-monthly, long-acting injectable atypical antipsychotic, following deltoid and gluteal administration in adult subjects with schizophrenia". Schizophr. Res. 159 (2–3): 404–10. doi:10.1016/j.schres.2014.09.021. PMID 25266547. S2CID 1036686.

[pmid26114240-5] Meltzer HY, Risinger R, Nasrallah HA, Du Y, Zummo J, Corey L, Bose A, Stankovic S, Silverman BL, Ehrich EW (2015). "A randomized, double-blind, placebo-controlled trial of aripiprazole lauroxil in acute exacerbation of schizophrenia". J Clin Psychiatry. 76 (8): 1085–90. doi:10.4088/JCP.14m09741. PMID 26114240.

[pmid26573020-6] Citrome L (2015). "Aripiprazole Long-Acting Injectable Formulations for Schizophrenia: Aripiprazole Monohydrate and Aripiprazole Lauroxil". Expert Rev Clin Pharmacol. 9 (2): 169–86. doi:10.1586/17512433.2016.1121809. PMID 26573020. S2CID 207208248.

[7] "Aristada (Aripiprazole lauroxil) FDA Approval History".

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