Pheniprazine

Last updated
Pheniprazine
Pheniprazine.png
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (1-Methyl-2-phenyl-ethyl)hydrazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.215 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C9H14N2
Molar mass 150.225 g·mol−1
  • InChI=1S/C9H14N2/c1-8(11-10)7-9-5-3-2-4-6-9/h2-6,8,11H,7,10H2,1H3 Yes check.svgY
  • Key:VXTWEDPZMSVFEF-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Pheniprazine (INN; also known as amphethydrazine and amphetamine hydrazide; brand names Catron and Cavodil; codename JB-516) is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine chemical class that was used as an antidepressant in the 1960s. [1] [2] [3] It was also used in the treatment of angina pectoris and schizophrenia. [4] [5] Pheniprazine has been largely discontinued due to toxicity concerns such as jaundice, amblyopia, and optic neuritis. [6] [7] [8]

See also

Related Research Articles

<span class="mw-page-title-main">Monoamine oxidase inhibitor</span> Type of medication

Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, especially for treatment-resistant depression and atypical depression. They are also used to treat panic disorder, social anxiety disorder, Parkinson's disease, and several other disorders.

<span class="mw-page-title-main">Phenelzine</span> Antidepressant

Phenelzine, sold under the brand name Nardil, among others, is a non-selective and irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class which is primarily used as an antidepressant and anxiolytic. Along with tranylcypromine and isocarboxazid, phenelzine is one of the few non-selective and irreversible MAOIs still in widespread clinical use. It is typically available in 15 mg tablets and doses usually range from 45–90 mg per day.

<span class="mw-page-title-main">Tranylcypromine</span> Irreversible non-selective MAO inhibitor Antidepressant drug

Tranylcypromine, sold under the brand name Parnate among others, is a monoamine oxidase inhibitor (MAOI). More specifically, tranylcypromine acts as nonselective and irreversible inhibitor of the enzyme monoamine oxidase (MAO). It is used as an antidepressant and anxiolytic agent in the clinical treatment of mood and anxiety disorders, respectively.

<span class="mw-page-title-main">Selegiline</span> Monoamine oxidase inhibitor

Selegiline, also known as L-deprenyl and sold under the brand names Eldepryl and Emsam among others, is a medication which is used in the treatment of Parkinson's disease and major depressive disorder. It is provided in the form of a capsule or tablet taken by mouth for Parkinson's disease and as a patch applied to skin for depression.

<span class="mw-page-title-main">Isocarboxazid</span> Antidepressant

Isocarboxazid is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class used as an antidepressant. Along with phenelzine and tranylcypromine, it is one of only three classical MAOIs still available for clinical use in the treatment of psychiatric disorders in the United States, though it is not as commonly employed in comparison to the others.

<span class="mw-page-title-main">Moclobemide</span> Antidepressant

Moclobemide, sold under the brand names Amira, Aurorix, Clobemix, Depnil and Manerix among others, is a reversible inhibitor of monoamine oxidase A (RIMA) drug primarily used to treat depression and social anxiety. It is not approved for use in the United States, but is approved in other Western countries such as Canada, the UK and Australia. It is produced by affiliates of the Hoffmann–La Roche pharmaceutical company. Initially, Aurorix was also marketed by Roche in South Africa, but was withdrawn after its patent rights expired and Cipla Medpro's Depnil and Pharma Dynamic's Clorix became available at half the cost.

<span class="mw-page-title-main">Iproniazid</span> Antidepressant

Iproniazid is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class. It is a xenobiotic that was originally designed to treat tuberculosis, but was later most prominently used as an antidepressant drug. However, it was withdrawn from the market because of its hepatotoxicity. The medical use of iproniazid was discontinued in most of the world in the 1960s, but remained in use in France until its discontinuation in 2015.

<span class="mw-page-title-main">Iproclozide</span> Chemical compound

Iproclozide is an irreversible and selective monoamine oxidase inhibitor (MAOI) of the hydrazine chemical class that was used as an antidepressant, but has since been discontinued. It has been known to cause fulminant hepatitis and there have been at least three reported fatalities due to administration of the drug.

<span class="mw-page-title-main">Pargyline</span> Chemical compound

Pargyline (brand name Eutonyl) is an irreversible selective monoamine oxidase (MAO)-B inhibitor drug (IC50 for MAO-A is 0.01152 μmol/L and for MAO-B is 0.00820 μmol/L) It was brought to market in the US and the UK by Abbott in 1963 as an antihypertensive drug branded "Eutonyl". It was one of several MAO inhibitors introduced in the 1960s including nialamide, isocarboxazid, phenelzine, and tranylcypromine. By 2007 the drug was discontinued and as of 2014 there were no generic versions available in the US. In addition to its actions as an MAOI, pargyline has been found to bind with high affinity to the I2 imidazoline receptor (an allosteric site on the MAO enzyme).

<span class="mw-page-title-main">Monoamine oxidase B</span> Protein-coding gene in the species Homo sapiens

Monoamine oxidase B, also known as MAOB, is an enzyme that in humans is encoded by the MAOB gene.

<span class="mw-page-title-main">Mebanazine</span>

Mebanazine is a monoamine oxidase inhibitor (MAOI) of the hydrazine chemical class that was previously used as an antidepressant in the 1960s, but has since been withdrawn due to hepatotoxicity.

<span class="mw-page-title-main">Metfendrazine</span> Chemical compound

Metfendrazine, also known as methphendrazine, is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine chemical class. It was investigated as an antidepressant, but was never marketed.

<span class="mw-page-title-main">Phenoxypropazine</span> Chemical compound

Phenoxypropazine is an irreversible and non-selective monoamine oxidase inhibitor (MAOI) of the hydrazine family. It was introduced as an antidepressant in 1961, but was subsequently withdrawn in 1966 due to hepatotoxicity concerns.

<span class="mw-page-title-main">Pivhydrazine</span>

Pivhydrazine, also known as pivalylbenzhydrazine and pivazide, is an irreversible and non-selective monoamine oxidase inhibitor (MAOI) of the hydrazine family. It was formerly used as an antidepressant in the 1960s, but has since been discontinued.

<span class="mw-page-title-main">Hydrazine (antidepressant)</span> Group of antidepressants

The hydrazine antidepressants are a group of non-selective, irreversible monoamine oxidase inhibitors (MAOIs) which were discovered and initially marketed in the 1950s and 1960s. Most have been withdrawn due to toxicity, namely hepatotoxicity, but a few still remain in clinical use.

Octamoxin, also known as 2-octylhydrazine, is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant in the 1960s but is now no longer marketed.

<span class="mw-page-title-main">Almoxatone</span> Chemical compound

Almoxatone (MD-780,236) is a selective and reversible inhibitor of MAO-B. It was patented as an antidepressant and antiparkinsonian agent but was never marketed.

Tetrindole was a drug candidate that functions by reversibly inhibiting monoamine oxidase A; it was first synthesized in Moscow in the early 1990s. Tetrindole is similar in its chemical structure to pirlindole (Pyrazidol), and metralindole.

The psychopharmacology revolution covers the introduction of various psychiatric drugs into clinical practice as well as their continued development. Although not exclusively limited to the 1950s period, the literature tends to suggest that this decade was a particularly fruitful time for CNS drug discovery and it has been referred to as a "golden era".

<span class="mw-page-title-main">Mofegiline</span>

Mofegiline (MDL-72,974) is a selective, irreversible inhibitor of monoamine oxidase B (MAO-B) and semicarbazide-sensitive amine oxidase (SSAO) which was under investigation for the treatment of Parkinson's disease and Alzheimer's disease, but was never marketed.

References

  1. Lear TE, Browne MW, Greeves JA (November 1962). "A controlled trial of cavodil (pheniprazine) in depression". The Journal of Mental Science. 108 (457): 856–58. doi:10.1192/bjp.108.457.856. PMID   13928843.
  2. Fagervall I, Ross SB (April 1986). "Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors". Biochemical Pharmacology. 35 (8): 1381–7. doi:10.1016/0006-2952(86)90285-6. PMID   2870717.
  3. Eberson LE, Persson K (July 1962). "Studies on Monoamine Oxidase Inhibitors. I. The Autoxidation of β-Phenylisopropylhydrazine as a Model Reaction for Irreversible Monoamine Oxidase Inhibition". Journal of Medicinal and Pharmaceutical Chemistry. 91 (4): 738–52. doi:10.1021/jm01239a006. PMID   14056405.
  4. Sandler G (March 1961). "Clinical evaluation of pheniprazine in angina pectoris". British Medical Journal. 1 (5228): 792–4. doi:10.1136/bmj.1.5228.792. PMC   1953879 . PMID   13746179.
  5. Wickstrom L, Hahn N (September 1962). "[beta-Phenylisoprophlhydrazine (Catran) in schizophrenia]". Nordisk Medicin. 68: 1165–7. PMID   14000469.
  6. Fentem PH, Howitt G (December 1961). "Fatal jaundice after administration of pheniprazine". British Medical Journal. 2 (5267): 1616–7. doi:10.1136/bmj.2.5267.1616. PMC   1970739 . PMID   13892290.
  7. Frandsen E (1962). "Toxic amblyopia during antidepressant treatment with pheniprazine (Catran)". Acta Psychiatrica Scandinavica. 38 (1): 1–14. doi:10.1111/j.1600-0447.1962.tb01780.x. PMID   13894598. S2CID   35152293.
  8. Thomsen NJ (January 1963). "[Optic neuritis after treatment with Catran]". Ugeskrift for Laeger. 125: 138–9. PMID   13981222.