U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H16ClN3O
Molecular Weight 313.781
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMOXAPINE

SMILES

ClC1=CC=C2OC3=CC=CC=C3N=C(N4CCNCC4)C2=C1

InChI

InChIKey=QWGDMFLQWFTERH-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Amoxapine is an antidepressant of the dibenzoxazepine class, chemically distinct from the dibenzazepines, dibenzocycloheptenes, and dibenzoxepines. It is designated chemically as 2-Chloro-11- (1-piperazinyl)dibenz[b,f ][1,4]oxazepine. Amoxapine is an antidepressant with a mild sedative component to its action. The mechanism of its clinical action in man is not well understood. In animals, amoxapine reduced the uptake of norepinephrine and serotonin and blocked the response of dopamine receptors to dopamine. Amoxapine is not a monoamine oxidase inhibitor. Amoxapine is absorbed rapidly and reaches peak blood levels approximately 90 minutes after ingestion. It is almost completely metabolized. The main route of excretion is the kidney. In vitro tests show that amoxapine binding to human serum is approximately 90%. In man, amoxapine serum concentration declines with a half-life of eight hours. However, the major metabolite, 8-hydroxyamoxapine, has a biologic half-life of 30 hours. Metabolites are excreted in the urine in conjugated form as glucuronides. Clinical studies have demonstrated that amoxapine has a more rapid onset of action than either amitriptyline or imipramine. The initial clinical effect may occur within four to seven days and occurs within two weeks in over 80% of responders.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Amoxapine-associated acute renal failure.
1985 Jun
Chronic but not acute treatment with antidepressants enhances the electroconvulsive seizure response in rats.
1985 Oct
Biochemical evidence that high concentrations of the antidepressant amoxapine may cause inhibition of mitochondrial electron transport.
1988 Mar 30
A possible mechanism of toxicity by the antidepressant amoxapine based on its effects in three in vitro models.
1989
The clinical pharmacology of depressive states.
2002 Mar
The role of substance P in depression: therapeutic implications.
2002 Mar
The pharmacological management of depression.
2005
Remarkable effect of selegiline (L-deprenyl), a selective monoamine oxidase type-B inhibitor, in a patient with severe refractory depression: a case report.
2005 Jul-Aug
Treatments in depression.
2006
A fully automated turbulent-flow liquid chromatography-tandem mass spectrometry technique for monitoring antidepressants in human serum.
2006 Feb
Risperidone in the treatment of psychotic depression.
2006 Jun
Solid-phase extraction and analysis of 20 antidepressant drugs in human plasma by LC/MS with SSI method.
2006 Oct 16
Pharmacological properties of glycine uptake in the developing rat retina.
2006 Sep
Detection and treatment of akathisia in advanced cancer patients during adjuvant analgesic therapy with tricyclic antidepressants: case reports and review of the literature.
2007 Dec
Amoxapine as an antipsychotic: comparative study versus haloperidol.
2007 Dec
Sweet's syndrome--a comprehensive review of an acute febrile neutrophilic dermatosis.
2007 Jul 26
Differential distribution of glycine transporters in Müller cells and neurons in amphibian retinas.
2007 Mar-Apr
Pharmacological causes of hyperprolactinemia.
2007 Oct
Prevalence and predictors of antidepressant use in a cohort of pregnant women.
2007 Sep
Effects of different antidepressant treatments on the core of depression.
2008
An autopsy case of poisoning with ethanol and psychotropic drugs.
2008 Apr
Suicidal antidepressant overdoses: a comparative analysis by antidepressant type.
2008 Dec
Amoxapine-associated acute respiratory distress.
2008 Jan
Determination of tricyclic antidepressants in human plasma using pipette tip solid-phase extraction and gas chromatography-mass spectrometry.
2008 Jul
Functional expression of the glycine transporter 1 on bullfrog retinal cones.
2008 Nov 19
Effectiveness of a multifactorial cardiovascular risk reduction clinic for diabetes patients with depression.
2008 Oct
Depression following thrombotic cardiovascular events in elderly medicare beneficiaries: risk of morbidity and mortality.
2009
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
5-Hydroxytryptamine Receptor Subtypes and their Modulators with Therapeutic Potentials.
2009 Jun
Persistence and compliance to antidepressant treatment in patients with depression: a chart review.
2009 Jun 16
Accuracy of Veterans Affairs databases for diagnoses of chronic diseases.
2009 Oct
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Amoxapine-induced tardive dyskinesia.
2009 Oct-Dec
A new strategy for antidepressant prescription.
2010
Syndrome of inappropriate secretion of anti-diuretic hormone in an elderly depressive patient receiving paroxetine: a case report.
2010 Apr
Validation of HPLC-MS/MS methods for analysis of loxapine, amoxapine, 7-OH-loxapine, 8-OH-loxapine and loxapine N-oxide in human plasma.
2010 Dec
Evaluation and performance of desorption electrospray ionization using a triple quadrupole mass spectrometer for quantitation of pharmaceuticals in plasma.
2010 Feb
Amoxapine inhibits the delayed rectifier outward K+ current in mouse cortical neurons via cAMP/protein kinase A pathways.
2010 Feb
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.
2010 Feb 23
Hallucinations: Clinical aspects and management.
2010 Jan
Direct agonist activity of tricyclic antidepressants at distinct opioid receptor subtypes.
2010 Jan
Drug-drug interaction between oxycodone and adjuvant analgesics in blood-brain barrier transport and antinociceptive effect.
2010 Jan
Seizure risk associated with neuroactive drugs: data from the WHO adverse drug reactions database.
2010 Mar
Multiple mechanisms of hERG liability: K+ current inhibition, disruption of protein trafficking, and apoptosis induced by amoxapine.
2010 May
Chem2Bio2RDF: a semantic framework for linking and data mining chemogenomic and systems chemical biology data.
2010 May 17
Gene expression profile analysis of genes in rat hippocampus from antidepressant treated rats using DNA microarray.
2010 Nov 30
Refractory hypotension during general anaesthesia caused by the long-term use of amoxapine.
2010 Sep
Inhibition of G protein-activated inwardly rectifying K+ channels by different classes of antidepressants.
2011
In vitro identification of the human cytochrome p450 enzymes involved in the oxidative metabolism of loxapine.
2011 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Usual effective dosage is 200 to 300 mg daily. Three weeks constitutes an adequate period of trial providing dosage has reached 300 mg daily (or lower level of tolerance) for at least two weeks. If no response is seen at 300 mg, dosage may be increased, depending upon tolerance, up to 400 mg daily.
Route of Administration: Oral
In Vitro Use Guide
Cells (mouse cortical neurons) were incubated with or without amoxapine varying concentrations of 10, 50, and 100 uM. At a concentration of 10 to 500 uM, amoxapine reversibly inhibited I(K) in a dose-dependent manner and modulated both steady-state activation and inactivation properties.
Name Type Language
AMOXAPINE
INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
AMOXAPINE [VANDF]
Common Name English
2-CHLORO-11-(1-PIPERAZINYL)DIBENZ(B,F)(1,4)OXAZEPINE
Systematic Name English
CL-67,772
Code English
DIBENZ(B,F)(1,4)OXAZEPINE, 2-CHLORO-11-(1-PIPERAZINYL)-
Systematic Name English
AMOXAPINE [INN]
Common Name English
AMOXAPINE [USP-RS]
Common Name English
CL 67772
Code English
AMOXAPINE [USP]
Common Name English
CL 67,772
Code English
LOXAPINE SUCCINATE IMPURITY, AMOXAPINE- [USP]
Common Name English
AMOXAPINE [MI]
Common Name English
AMOXAPINE [JAN]
Common Name English
AMOXAPINE [WHO-DD]
Common Name English
AMOXAPINE [ORANGE BOOK]
Common Name English
ASENDIN
Brand Name English
AMOXAPINE [MART.]
Common Name English
AMOXAPINE [USAN]
Common Name English
CL-67772
Code English
Classification Tree Code System Code
WHO-VATC QN06AA17
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
NDF-RT N0000175752
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
WHO-ATC N06AA17
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
LIVERTOX 48
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
NCI_THESAURUS C94727
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
Code System Code Type Description
EVMPD
SUB05479MIG
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
RXCUI
722
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY RxNorm
CAS
14028-44-5
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
IUPHAR
201
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
MERCK INDEX
M1843
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
237-867-1
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
INN
3049
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
DRUG BANK
DB00543
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
EPA CompTox
14028-44-5
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
WIKIPEDIA
Amoxapine
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
PUBCHEM
2170
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
MESH
D000657
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
LactMed
14028-44-5
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
ChEMBL
CHEMBL1113
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY
NCI_THESAURUS
C47397
Created by admin on Tue Oct 22 00:28:19 UTC 2019 , Edited by admin on Tue Oct 22 00:28:19 UTC 2019
PRIMARY