Amoxapine

Amoxapine

Clinical data
Trade names	Asendin, Asendis, Defanyl, Demolox
AHFS/Drugs.com	Monograph
MedlinePlus	a682202
License data	US FDA: Amoxapine
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	N06AA17 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	>60%
Protein binding	90%
Metabolism	Hepatic ()
Biological half-life	8–10 hours (30 hours for chief active metabolite)
Excretion	Renal (60%), faeces (18%)
Identifiers
IUPAC name 2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine
CAS Number	14028-44-5 Y
PubChem (CID)	2170
IUPHAR/BPS	201
DrugBank	DB00543 Y
ChemSpider	2085 Y
UNII	R63VQ857OT Y
KEGG	D00228 Y
ChEBI	CHEBI:2675 Y
ChEMBL	CHEMBL1113 Y
ECHA InfoCard	100.034.411
Chemical and physical data
Formula	C17H16ClN3O
Molar mass	313.781 g/mol
3D model (Jmol)	Interactive image
SMILES Clc2ccc1Oc4c(/N=C(\c1c2)N3CCNCC3)cccc4
InChI InChI=1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2 Y Key:QWGDMFLQWFTERH-UHFFFAOYSA-N Y

Amoxapine (pronounced: a-mox-a-peen. Notable brand names include: Asendin, Asendis, Defanyl, Demolox. See here for more brand name information) is a tetracyclic antidepressant of the dibenzoxazepine family, though it is often classified as a tricyclic antidepressant. It is the N-demethylated metabolite of loxapine. It first received marketing approval in the US in 1992 (approximately thirty to forty years after most of the other tricyclic antidepressants were introduced in the US).

Amoxapine is used in the treatment of major depressive disorder. Compared to other antidepressants it is believed to have a faster onset of action, with therapeutic effects seen within four to seven days. In excess of 80% of patients that do respond to amoxapine are reported to respond within a fortnight of the beginning of treatment. It also has properties similar to those of the atypical antipsychotics, and may behave as one and may be used in the treatment of schizophrenia off-label. Despite its apparent lack of extrapyramidal side effects in patients with schizophrenia it has been found to exacerbate motor symptoms in patients with Parkinson's disease psychosis.

Adverse effects by incidence:
Note: Serious (that is, those that can either result in permanent injury or are irreversible or are potentially life-threatening) are written in bold text.
Very common (>10% incidence) adverse effects include:

Common (1-10% incidence) adverse effects include:

Uncommon/Rare (<1% incidence) adverse effects include:

Unknown incidence or relationship to drug treatment adverse effects include:

It tends to produce less anticholinergic effects, sedation and weight gain than some of the earlier tricyclic antidepressants (e.g. amitriptyline, clomipramine, doxepin, imipramine and trimipramine). It may also be less cardiotoxic than its predecessors.