Loxapine

Loxapine
Clinical data
Trade names	Loxitane, Adasuve
AHFS/Drugs.com	Monograph
MedlinePlus	a682311
License data	EU EMA: by INN; US DailyMed: Loxapine; US FDA: Loxapine;
Routes of; administration	By mouth, inhalation, intramuscular
Drug class	Antipsychotic
ATC code	N05AH01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Protein binding	96.8%
Metabolism	Extensive Liver; active metabolites include amoxapine and 8-hydroxyloxapine. Inhibits P-gp and is a substrate of CYP1A2, CYP3A4 and CYP2D6
Elimination half-life	4 hours (oral); 7.61 hours (inhalation)
Excretion	Majority are excreted within 24 hours, main route through urine (conjugated metabolites), small amounts through the feces (unconjugated metabolites)
Identifiers
	IUPAC name 8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzoxazepine;
CAS Number	1977-10-2 ;
PubChem CID	3964;
IUPHAR/BPS	205;
DrugBank	DB00408 ;
ChemSpider	3827 ;
UNII	LER583670J;
KEGG	D02340 ;
ChEBI	CHEBI:50841 ;
ChEMBL	ChEMBL831 ;
CompTox Dashboard (EPA)	DTXSID7023229 ;
ECHA InfoCard	100.016.215
Chemical and physical data
Formula	C18H18ClN3O
Molar mass	327.81 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	109 to 110 °C (228 to 230 °F)
	SMILES Clc2ccc1Oc4c(/N=C(\c1c2)N3CCN(C)CC3)cccc4;
	InChI InChI=1S/C18H18ClN3O/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18/h2-7,12H,8-11H2,1H3 ; Key:XJGVXQDUIWGIRW-UHFFFAOYSA-N ;
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Loxapine, sold under the brand names Loxitane and Adasuve (inhalation only) among others, is a tricyclic^[3] antipsychotic medication used primarily in the treatment of schizophrenia. The medicine is a member of the dibenzoxazepine class and structurally very similar to clozapine. Several researchers have argued that loxapine, initially classified as a typical antipsychotic, behaves as an atypical antipsychotic.^[4]

Loxapine may be metabolized by N-demethylation to amoxapine, a tricyclic antidepressant.^[5]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b ^c Truven Health Analytics, Inc. DrugPoint System (Internet) [cited 2013 Sep 21]. Greenwood Village, CO: Thomsen Healthcare; 2013.
^ Popovic D, Nuss P, Vieta E (2015-04-01). "Revisiting loxapine: a systematic review". Annals of General Psychiatry. 14 15. doi:10.1186/s12991-015-0053-3. PMC 4391595. PMID 25859275.
^ Glazer WM (1999). "Does loxapine have "atypical" properties? Clinical evidence". The Journal of Clinical Psychiatry. 60 Suppl 10 (Suppl 10): 42–46. PMID 10340686.
^ Cheung SW, Tang SW, Remington G (March 1991). "Simultaneous quantitation of loxapine, amoxapine and their 7- and 8-hydroxy metabolites in plasma by high-performance liquid chromatography". Journal of Chromatography. 564 (1): 213–221. doi:10.1016/0378-4347(91)80083-O. PMID 1860915.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[DrugPoint-2] Truven Health Analytics, Inc. DrugPoint System (Internet) [cited 2013 Sep 21]. Greenwood Village, CO: Thomsen Healthcare; 2013.

[3] Popovic D, Nuss P, Vieta E (2015-04-01). "Revisiting loxapine: a systematic review". Annals of General Psychiatry. 14 15. doi:10.1186/s12991-015-0053-3. PMC 4391595. PMID 25859275.

[Glazer_1999-4] Glazer WM (1999). "Does loxapine have "atypical" properties? Clinical evidence". The Journal of Clinical Psychiatry. 60 Suppl 10 (Suppl 10): 42–46. PMID 10340686.

[Cheung_1991-5] Cheung SW, Tang SW, Remington G (March 1991). "Simultaneous quantitation of loxapine, amoxapine and their 7- and 8-hydroxy metabolites in plasma by high-performance liquid chromatography". Journal of Chromatography. 564 (1): 213–221. doi:10.1016/0378-4347(91)80083-O. PMID 1860915.

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