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[[Image:|200px|Phenelzine chemical structure]]
Phenelzine

2-hydrazinylethylbenzene
IUPAC name
CAS number
51-71-8
ATC code

N06AF03

PubChem
3675
DrugBank
APRD00099
Chemical formula {{{chemical_formula}}}
Molecular weight 136.194 g/mol
Bioavailability
Metabolism Liver
Elimination half-life 11 hours
Excretion Urine
Pregnancy category C (USA)
B3 (Aus)
Legal status
Routes of administration Oral

Phenelzine (sold as Nardil) is a monoamine oxidase inhibitor (MAOI) used as an antidepressant drug.

Mode of actionEdit

Phenelzine is a derivative of hydrazine, which is phenylethylamine-like moiety and similar to normal substrates of MAO. When MAO tries to oxidize phenelzine, this hydrazine-moiety binds covalently to the enzyme, thus inactivating it irreversibly. Phenelzine is a non-selective MAO-inhibitor, it inhibits both MAO-A and MAO-B. Furthermore, primarily through its primary metabolite, PEH (phenylethylidenehydrazine), phenelzine elevates levels of GABA in the caudate-putamen and nucleus accumbens. This may contribute to its anxiolytic properties and superior efficacy in treating severe anxiety.

PharmacokineticsEdit

Phenelzine is administered orally as phenelzine sulfate and it is rapidly absorbed from the gastro-intestinal tract. Although phenelzine has a fairly short half-life, its effect lasts for several weeks, until new functional MAO-enzymes have been produced by the body. Phenelzine is acetylated in the liver and its metabolites are excreted in the urine.

Side effectsEdit

Common side effects include orthostatic hypotension, dizziness, headache, fatigue, insomnia, sexual difficulty, hesitant urination. Most of these side effects dissipate with time and/or careful adjustments of the dosage.

Hypertensive Crises Edit

As with other MAOIs, tyramine-containing foods cause a hypertensive crisis, so users of phenelzine should adhere to certain dietary guidelines, primarily consisting of avoiding certain aged wines and spirits, and certain aged cheeses. The prescribing Doctor will advise patients on this issue. The tyramine induced hypertensive crises is estimated to effect only a few percent of the population. It is possible to test patients to see if they are at risk.

Nardil formulationEdit

Nardil was changed in late 2003, due to a complete reformulation by Pfizer, who removed many of the excipient ingredients, including the hard coating. It is possible that the current version is not surviving the stomach acid content and therefore not as much is being absorbed into the bloodstream. It is also possible that the machinery used to mix and manufacture Nardil is, since Pfizer acquired the medication, not able to sufficiently blend and mix the medication, making parts or all of some lots irregular in the content of medication delivered to the system.

Many users continue to experience difficulties following this change. The indicated dosage has not been altered by Pfizer, nor did they advise physicians or pharmacies of these changes, yet the recommended dosage seems not to have the desired effect on many. It is believed that, currently, there are some 75,000 to 85,000 people taking Nardil worldwide. The original formulation of Nardil is no longer available. Nardil is no longer manufactured by Pfzier. It is now produced by Concord Pharmaceuticals in the UK.


Indicated forEdit

ReferencesEdit

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Antidepressants (ATC N06A) edit
Monoamine oxidase inhibitors (MAOI) Harmaline, Iproclozide, Iproniazid, Isocarboxazid, Nialamide, Phenelzine, Selegiline, Toloxatone, Tranylcypromine
Reversible inhibitor of monoamine oxidase A (RIMA) Brofaromine, Moclobemide
Dopamine reuptake inhibitor (DARI) Amineptine, Phenmetrazine, Vanoxerine, Modafinil
Norepinephrine-dopamine reuptake inhibitors Bupropion
Norepinephrine reuptake inhibitor (NRI) or (NARI) Atomoxetine, Maprotiline, Reboxetine, Viloxazine
Serotonin-norepinephrine reuptake inhibitor (SNRI) Duloxetine, Milnacipran, Venlafaxine
Selective serotonin reuptake inhibitor (SSRI) Alaproclate, Etoperidone, Citalopram, Escitalopram, Fluoxetine, Fluvoxamine, Paroxetine, Sertraline, Zimelidine
Selective serotonin reuptake enhancer (SSRE) Tianeptine
Tricyclic antidepressants (TCA) Amitriptyline, Amoxapine, Butriptyline, Clomipramine, Desipramine, Dibenzepin, Dothiepin, Doxepin, Imipramine, Iprindole, Lofepramine, Melitracen, Nortriptyline, Opipramol, Protriptyline, Trimipramine
Tetracyclic antidepressants Maprotiline, Mianserin, Nefazodone, Trazodone
Noradrenergic and specific serotonergic antidepressant (NaSSA) Mirtazapine
pl:Fenelzyna
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