Structure via PubChem · Public domain (PubChem)
amoxapine
Sign in to saveAlso known as amoxipine, Asendin®, Desmethylloxapin, 2-Chloro-11-(1-piperazinyl)dibenz(b,f)(1,4)oxazepine, Amoxapinum, Amoxapin, Amoxapina
Amoxapine, sold under the brand name Asendin among others, is a tricyclic antidepressant (TCA). It is the N-demethylated 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.
Chemical data
- Formula
- C17H16ClN3O
- Molecular weight
- 313.8 g/mol
- IUPAC name
- 8-chloro-6-piperazin-1-ylbenzo[b][1,4]benzoxazepine
- SMILES
- C1CN(CCN1)C2=NC3=CC=CC=C3OC4=C2C=C(C=C4)Cl
- InChIKey
- QWGDMFLQWFTERH-UHFFFAOYSA-N
- XLogP
- 2.6
- Polar surface area
- 36.9 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
504 papers- Amoxapine.2006
- Amoxapine.2012
- Amoxapine.2026
- Evaluation of amoxapine.Clinical pharmacy · 1982
- Amoxapine (Asendin, Lederle Laboratories).Drug intelligence & clinical pharmacy · 1982
via PubMed
Wikidata facts
- Mass
- 313.098
Show 5 more facts
- chemical formula
- C₁₇H₁₆ClN₃O
- Commons category
- Amoxapine
- canonical SMILES
- C1CN(CCN1)C2=NC3=CC=CC=C3OC4=C2C=C(C=C4)Cl
- World Health Organisation international non-proprietary name
- amoxapine
- defined daily dose
- 0.15
Sources (8)
via Wikidata · CC0
~7 min read
Article
12 sectionsContents
- Medical uses
- Contraindications
- Lactation
- Side effects
- Overdose
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Society and culture
- Brand names
- See also
- References
Amoxapine, sold under the brand name Asendin among others, is a tricyclic antidepressant (TCA). It is the N-demethylated 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.
==Medical uses== 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 two weeks of the beginning of treatment. It also has properties similar to those of the atypical antipsychotics, and may behave as one and thus 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 worsen motor function in a study of three patients with Parkinson's disease and psychosis.