Amoxapine

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Structural formula
Amoxapine structural formula
General
Non-proprietary name Amoxapine
other names

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

Molecular formula C 17 H 16 ClN 3 O
External identifiers / databases
CAS number 14028-44-5
EC number 237-867-1
ECHA InfoCard 100.034.411
PubChem 2170
DrugBank DB00543
Wikidata Q58356
Drug information
ATC code

N06 AA17

Drug class

Tricyclic antidepressant

properties
Molar mass 313.78 g mol −1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Amoxapine one of the dibenzazepine - derivatives ( dibenzoxazepines ) and is called the drug from the group of tricyclic antidepressants used. The active ingredient was patented by American Cyanamid in 1966 .

pharmacology

Pharmacodynamics

Amoxapine inhibits v. a. the resumption of the messenger substance norepinephrine . In addition, it acts as a weak serotonin reuptake inhibitor while at the same time blocking the 5-HT 2 receptor . One of its main metabolites, 7-hydroxyamoxapine , acts as an antagonist at the D 2 receptor . It also has anticholinergic and antihistaminic effects on the H 1 receptor. In terms of effects and side effects, it corresponds to the imipramine type.

Pharmacokinetics

Amoxapine is absorbed relatively quickly, so that it develops its maximum effect (T max ) after just 90 minutes . The bioavailability is 90%. It is almost completely metabolised by the CYP-450 enzyme system and mainly excreted by the kidneys. The half-life is eight hours, but 30 hours for its active metabolite 8-hydroxyamoxapine. In clinical studies, the antidepressant effects of amoxapine have been found to develop faster than amitriptyline or imipramine.

Clinical information

Application areas (indications)

Amoxapine is approved for the treatment of depression , bipolar disorder, and panic disorder . Therapeutically sensible doses range between 200 and 300 mg daily, in-patient treatment can be increased to 600 mg if necessary.

It has also been shown that amoxapine can be used to treat schizophrenia . In studies, it was found to be as effective as haloperidol and risperidone . The extrapyramidal syndrome is said to have occurred less often and the prolactin level to be increased less often. With the negative symptoms of schizophrenia, it is said to work better than haloperidol.

Adverse effects (side effects)

Common side effects (<1%) are: anxiety, nervousness, confusion, nausea, increased appetite, headache, weakness, insomnia, nightmares, tremors, ataxia, palpitations , edema , exanthema , increased prolactin level , increased sweating. A very rare but dangerous side effect is the neuroleptic malignant syndrome .

Drug interactions

It has been observed that drugs that inhibit the cytochrome P450-2D6 enzyme hinder the breakdown of amoxapine, so the dose must be reduced.

literature

  • Mosby Year-Book, Inc .: Physician's GenRx: The Complete Drug Reference. 5th edition. Denniston Publishing, Riverside, CT 1995.
  • T. Palfai, H. Jankiewicz: Drugs and Human Behavior. 2nd Edition. Brown & Benchmark, Madison, WI 1997.
  • D. Hedges, C. Burchfield: Mind, Brain, and Drug: An Introduction to Psychopharmacology. Pearson, Boston, MA 2006.

Trade names

Amoxapine is only approved as Defanyl in France in Europe .

Individual evidence

  1. a b Amoxapine data sheet from Sigma-Aldrich , accessed on March 9, 2011 ( PDF ).Template: Sigma-Aldrich / name not given
  2. Entry on amoxapine. In: Römpp Online . Georg Thieme Verlag, accessed on January 26, 2019.
  3. R. Apiquian, E. Ulloa, A. Fresan, C. Loyzaga, H. Nicolini, S. Kapur: Amoxapine shows atypical antipsychotic effects in patients with schizophrenia: results from a prospective open-label study. In: Schizophr Res. 1/2003, pp. 35-39. PMID 12413640 .
  4. IB Chaudhry, N. Husain, S. Khan, S. Badshah, B. Deakin, S. Kapur: Amoxapine as an antipsychotic: comparative study versus haloperidol. In: J Clin Psychopharmacol . 6/2007, pp. 575-581. PMID 18004123 .
  5. R. Apiquian, A. Fresan, RE Ulloa, C. de la Fuente-Sandoval, M. Herrera-Estrella, A. Vazquez, H. Nicolini, S. Kapur: Amoxapine as an atypical antipsychotic: a comparative study vs risperidone. In: Neuropsychopharmacology . 12/2005, pp. 2236-2244. PMID 15956984 .
  6. Index Nominum, online edition.