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Details

Stereochemistry ACHIRAL
Molecular Formula C17H16ClN3O
Molecular Weight 313.781
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMOXAPINE

SMILES

ClC1=CC2=C(OC3=C(C=CC=C3)N=C2N4CCNCC4)C=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

Molecular Formula C17H16ClN3O
Molecular Weight 313.781
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMOXAPINE
Primary
AMOXAPINE

Cmax

ValueDoseCo-administeredAnalytePopulation
33.55 ng/mL
50 mg single, oral
AMOXAPINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
319 ng × h/mL
50 mg single, oral
AMOXAPINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
6.02 h
50 mg single, oral
AMOXAPINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
50 mg single, oral
AMOXAPINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Tox targets

PubMed

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.
Substance Class Chemical
Record UNII
R63VQ857OT
Record Status Validated (UNII)
Record Version