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Merck

A129

Amoxapine

Synonyme(s) :

2-Chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine

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A propos de cet article

Formule empirique (notation de Hill) :
C17H16ClN3O
Numéro CAS:
Poids moléculaire :
313.78
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
237-867-1
MDL number:
Form:
powder
Quality level:
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InChI key

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

SMILES string

Clc1ccc2Oc3ccccc3N=C(N4CCNCC4)c2c1

form

powder

solubility

methanol: soluble

originator

Wyeth

Quality Level

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Application

Amoxapine has been used as an antidepressant drug to test its effect on locomotion and egg release in response to gain-of-functional mutations in potassium (K+) channels (unc-58) of C. elegans. It has also been used as an antipsychotic drug to test its effect on the viability of glioblastoma cells.

Biochem/physiol Actions

Amoxapine, a structural analog of clozapine, is a human ether a-go-go (hERG) channel blocker. It is also an N-methylated metabolite of loxapine. It is a tricyclic antidepressant that inhibits the uptake of norepinephrine and blocks 5- hydroxytryptamine (HT2 ) serotonergic receptors.

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Wyeth. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Consulter la Bibliothèque de documents

J E Dugas et al.
Drug intelligence & clinical pharmacy, 16(3), 199-204 (1982-03-01)
Amoxapine is a tricyclic antidepressant agent, which is chemically related to the antipsychotic agent loxapine, but which appears to block selectively the neuronal reuptake of norepinephrine; it is qualitatively similar to desipramine. In studies of patients with mixed depressive illnesses
T A Ban et al.
International pharmacopsychiatry, 15(3), 166-170 (1980-01-01)
Amoxapine, a new antidepressant, is a tricyclic debenzoxazepine compound, the demethylated metabolite of the neuroleptic loxapine. In animal pharmacological studies, amoxapine has shown striking similarities to imipramine. In contrast to the prototype antidepressant drug, however, amoxapine does not interact with
Sabrina Obers et al.
Naunyn-Schmiedeberg's archives of pharmacology, 381(5), 385-400 (2010-03-17)
The antidepressant amoxapine has been linked to cases of QT prolongation, acute heart failure, and sudden death. Inhibition of cardiac hERG (Kv11.1) potassium channels causes prolonged repolarization and is implicated in apoptosis. Apoptosis in association with amoxapine has not yet
S Kapur et al.
Biological psychiatry, 45(9), 1217-1220 (1999-05-20)
All currently available atypical antipsychotics have, at clinically relevant doses: i) high serotonin (5-HT)2 occupancy; ii) greater 5-HT2 than dopamine (D)2 occupancy; and iii) a higher incidence of extrapyramidal side effects when their D2 occupancy exceeds 80%. A review of
Yan-Lin He et al.
The Journal of pharmacology and experimental therapeutics, 332(2), 437-445 (2009-11-17)
Ion channels are known to be modulated by antidepressant drugs, but the molecular mechanisms are not known. We have shown that the antidepressant drug amoxapine suppresses rectifier outward K(+) (I(K)) currents in mouse cortical neurons. At a concentration of 10

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