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Loxapine information


Loxapine
Clinical data
Trade namesLoxitane, Adasuve
AHFS/Drugs.comMonograph
MedlinePlusa682311
License data
  • EU EMA: by INN
  • US DailyMed: Loxapine
  • US FDA: Loxapine
Routes of
administration
By mouth, inhalation, intramuscular
Drug classAntipsychotic
ATC code
  • N05AH01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[2]
  • US: WARNING[1]Rx-only
  • EU: Rx-only
Pharmacokinetic data
Protein binding96.8%[3]
MetabolismExtensive Liver; active metabolites include amoxapine and 8-hydroxyloxapine. Inhibits P-gp and is a substrate of CYP1A2, CYP3A4 and CYP2D6[3]
Elimination half-life4 hours (oral); 7.61 hours (inhalation)[3]
ExcretionMajority 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 checkY
PubChem CID
  • 3964
IUPHAR/BPS
  • 205
DrugBank
  • DB00408 ☒N
ChemSpider
  • 3827 checkY
UNII
  • LER583670J
KEGG
  • D02340 checkY
ChEBI
  • CHEBI:50841 ☒N
ChEMBL
  • ChEMBL831 checkY
CompTox Dashboard (EPA)
  • DTXSID7023229 Edit this at Wikidata
ECHA InfoCard100.016.215 Edit this at Wikidata
Chemical and physical data
FormulaC18H18ClN3O
Molar mass327.81 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point109 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 checkY
  • Key:XJGVXQDUIWGIRW-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)
Bottle containing loxapine capsules, a mid-potency antipsychotic.

Loxapine, sold under the brand names Loxitane and Adasuve (inhalation only) among others, is a tricyclic[4] 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.[5]

Loxapine may be metabolized by N-demethylation to amoxapine, a tricyclic antidepressant.[6]

  1. ^ "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.
  2. ^ 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.
  3. ^ a b c Truven Health Analytics, Inc. DrugPoint System (Internet) [cited 2013 Sep 21]. Greenwood Village, CO: Thomsen Healthcare; 2013.
  4. ^ 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.
  5. ^ Glazer WM (1999). "Does loxapine have "atypical" properties? Clinical evidence". The Journal of Clinical Psychiatry. 60 (Suppl 10): 42–46. PMID 10340686.
  6. ^ 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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counts to monitor potential neutropenia. Loxapine binds D2, D3 and D4 with high affinity; can also bind D1. Loxapine is often used to treat agitated and violent...

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tricyclic antidepressant (TCA). It is the N-demethylated metabolite of loxapine. Amoxapine first received marketing approval in the United States in 1980...

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is not used as an antidepressant and is instead used as an anxiolytic Loxapine (Adasuve, Loxitane) – a typical antipsychotic that produces amoxapine as...

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the Ed. Despite the molecular structure similarity between amoxapine and loxapine (molecules in group 2), the crystal packing observed in polymorphs of loxa...

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