Product Code Database
Amoxapine, sold under the brand name Asendin among others, is a tricyclic antidepressant (TCA). It is the N-demethylation metabolite of loxapine. Amoxapine first received marketing approval in the United States in 1980, approximately 10 to 20 years after most of the other TCAs were introduced in the United States.
Its use is also advised against in individuals concurrently on monoamine oxidase inhibitors or if they have been on one in the past 14 days and in individuals on drugs that are known to prolong the QT interval (e.g. ondansetron, citalopram, pimozide, sertindole, ziprasidone, haloperidol, chlorpromazine, thioridazine, etc.).
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 TCAs (e.g. amitriptyline, clomipramine, doxepin, imipramine, trimipramine). It may also be less cardiotoxic than its predecessors.
Amoxapine possesses a wide array of pharmacological effects. It is a moderate and strong reuptake inhibitor of serotonin and norepinephrine, respectively, and binds to the 5-HT2A, 5-HT2B, 5-HT2C, 5-HT3, 5-HT6, 5-HT7, D2, α1-adrenergic, D3, D4, and H1 receptors with varying but significant affinity, where it acts as an antagonist (or inverse agonist depending on the receptor in question) at all sites. It has weak but negligible affinity for the dopamine transporter and the 5-HT1A, 5-HT1B, D1, α2-adrenergic, H4, mACh, and GABAA receptor, and no affinity for the β-adrenergic receptors or the allosteric benzodiazepine site on the GABAA receptor. Amoxapine is also a weak GlyT2 blocker, as well as a weak (Ki = 2.5 μM, EC50 = 0.98 μM) δ-opioid receptor partial agonist.
7-Hydroxyamoxapine, a major active metabolite of amoxapine, is a more potent dopamine receptor antagonist and contributes to its neuroleptic efficacy, whereas 8-Hydroxyamoxapine is a norepinephrine reuptake inhibitor but a stronger serotonin reuptake inhibitor and helps to balance amoxapine's ratio of serotonin to norepinephrine transporter blockade.
Where:
Lactation
Its use in breastfeeding mothers not recommended as it is excreted in breast milk and the concentration found in breast milk is approximately a quarter that of the maternal serum level.
Side effects
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.
(2025). 9780702042935, Churchill Livingstone Elsevier. ISBN 9780702042935
Overdose
It is considered particularly toxic in overdose, with a high rate of renal failure (which usually takes 2–5 days), rhabdomyolysis, coma, seizures and even status epilepticus. Some believe it to be less cardiotoxic than other TCAs in overdose, although reports of cardiotoxic overdoses have been made.
Pharmacology
Pharmacodynamics
+ Amoxapine Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.
Pharmacokinetics
Amoxapine is metabolised into two main active metabolites: 7-hydroxyamoxapine and 8-hydroxyamoxapine.
Urine (60%), feces (18%) ? ?
Society and culture
Brand names
Brand names for amoxapine include (where † denotes discontinued brands):
See also
Categories: Alpha-1 Blockers, Atypical Antipsychotics, Chloroarenes, Delta-opioid Receptor Agonists, Dibenzoxazepines, Dopamine Antagonists, Glycine Reuptake Inhibitors, H1 Receptor Antagonists, Human Drug Metabolites, Muscarinic Antagonists, 1-piperazinyl Compounds, Serotonin Receptor Antagonists, Serotonin–norepinephrine Reuptake Inhibitors, Tetracyclic Antidepressants, Tricyclic Antidepressants
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