Bifemelane

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Bifemelane
Bifemelane.svg
Clinical data
Trade names Alnert, Celeport
Other namesMCl-2016
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
  • N-methyl-4-[2-(phenylmethyl)phenoxy]butan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.220.566 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H23NO
Molar mass 269.388 g·mol−1
3D model (JSmol)
  • O(c1ccccc1Cc2ccccc2)CCCCNC
  • InChI=1S/C18H23NO/c1-19-13-7-8-14-20-18-12-6-5-11-17(18)15-16-9-3-2-4-10-16/h2-6,9-12,19H,7-8,13-15H2,1H3 Yes check.svgY
  • Key:QSQQPMHPCBLLGX-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Bifemelane (INN) (Alnert, Celeport), or bifemelane hydrochloride (JAN), also known as 4-(O-benzylphenoxy)-N-methylbutylamine, is an antidepressant and cerebral activator that was widely used in the treatment of cerebral infarction patients with depressive symptoms in Japan, and in the treatment of senile dementia as well. [1] [2] It also appears to be useful in the treatment of glaucoma. [3] It has been discontinued in Japan since 1998, when it was removed from the market reportedly for lack of effectiveness. [4]

Bifemelane acts as a monoamine oxidase inhibitor of both isoenzymes, with competitive (reversible) inhibition of MAO-A (Ki = 4.20 μM) (making it a reversible inhibitor of monoamine oxidase A (RIMA)) and non-competitive (irreversible) inhibition of MAO-B (Ki = 46.0 μM), [5] [6] [7] and also acts (weakly) as a norepinephrine reuptake inhibitor. [8] The drug has nootropic, neuroprotective, and antidepressant-like effects in animal models, and appears to enhance the cholinergic system in the brain. [9] [10] [11]

See also

Related Research Articles

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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">Monoamine oxidase</span> Family of enzymes

Monoamine oxidases (MAO) are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The first such enzyme was discovered in 1928 by Mary Bernheim in the liver and was named tyramine oxidase. The MAOs belong to the protein family of flavin-containing amine oxidoreductases.

<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 family which is primarily used as an antidepressant and anxiolytic to treat depression and anxiety. Along with tranylcypromine and isocarboxazid, phenelzine is one of the few non-selective and irreversible MAOIs still in widespread clinical use.

<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. It is also effective in the treatment of ADHD.

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

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<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">Dosulepin</span> Antidepressant

Dosulepin, also known as dothiepin and sold under the brand name Prothiaden among others, is a tricyclic antidepressant (TCA) which is used in the treatment of depression. Dosulepin was once the most frequently prescribed antidepressant in the United Kingdom, but it is no longer widely used due to its relatively high toxicity in overdose without therapeutic advantages over other TCAs. It acts as a serotonin–norepinephrine reuptake inhibitor (SNRI) and also has other activities including antihistamine, antiadrenergic, antiserotonergic, anticholinergic, and sodium channel-blocking effects.

<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">Rasagiline</span> Chemical compound

Rasagiline, sold under the brand name Azilect among others, is a medication which is used in the treatment of Parkinson's disease. It is used as a monotherapy to treat symptoms in early Parkinson's disease or as an adjunct therapy in more advanced cases. The drug is taken by mouth.

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

Lofepramine, sold under the brand names Gamanil, Lomont, and Tymelyt among others, is a tricyclic antidepressant (TCA) which is used to treat depression. The TCAs are so named as they share the common property of having three rings in their chemical structure. Like most TCAs lofepramine is believed to work in relieving depression by increasing concentrations of the neurotransmitters norepinephrine and serotonin in the synapse, by inhibiting their reuptake. It is usually considered a third-generation TCA, as unlike the first- and second-generation TCAs it is relatively safe in overdose and has milder and less frequent side effects.

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

Pargyline, sold under the brand name Eutonyl among others, is a monoamine oxidase inhibitor (MAOI) medication which has been used to treat hypertension but is no longer marketed. It has also been studied as an antidepressant, but was never licensed for use in the treatment of depression. The drug is taken by mouth.

<span class="mw-page-title-main">Molindone</span> Antipsychotic medication

Molindone, sold under the brand name Moban, is an antipsychotic medication which is used in the United States in the treatment of schizophrenia. It is taken by mouth.

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

(–)-Benzofuranylpropylaminopentane is an experimental drug related to selegiline which acts as a monoaminergic activity enhancer (MAE). It is orally active in animals.

<span class="mw-page-title-main">Nefopam</span> Analgesic medication

Nefopam, sold under the brand name Acupan among others, is a centrally acting, non-opioid painkilling medication, with central stimulant and sympathomimetic properties that is primarily used to treat moderate to severe pain.

<span class="mw-page-title-main">Indeloxazine</span> Antidepressant and cerebral activator

Indeloxazine (INN) is an antidepressant and cerebral activator that was marketed in Japan and South Korea by Yamanouchi Pharmaceutical Co., Ltd for the treatment of psychiatric symptoms associated with cerebrovascular diseases, namely depression resulting from stroke, emotional disturbance, and avolition. It was marketed from 1988 to 1998, when it was removed from the market reportedly for lack of effectiveness.

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

Amiflamine (FLA-336) is a reversible inhibitor of monoamine oxidase A (MAO-A), thereby being a RIMA, and, to a lesser extent, semicarbazide-sensitive amine oxidase (SSAO), as well as a serotonin releasing agent (SRA). It is a derivative of the phenethylamine and amphetamine chemical classes. The (+)-enantiomer is the active stereoisomer.

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

Caroxazone is an antidepressant which was formerly used for the treatment of depression but is now no longer marketed. It acts as a reversible monoamine oxidase inhibitor (RIMA) of both MAO-A and MAO-B subtypes, with five-fold preference for the latter.

<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.

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

Bazinaprine (SR-95,191) is an experimental drug candidate. It is a monoamine oxidase inhibitor (MAOI) which is believed to be useful for the treatment of depression. The drug strongly inhibits type A monoamine oxidase, but only weakly inhibits type B. The effects of the drug are reversible in vivo, but not in vitro. In studies, the chemical has been shown to not interact in vivo with other neurotransmitter or drug receptor sites.

<span class="mw-page-title-main">SU-11739</span> Monoamine oxidase inhibitor

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References

  1. ↑ Koide S, Onishi H, Hashimoto H, Kai T, Katayama M, Yamagami S (1995). "Effects of bifemelane hydrochloride on plasma neuropeptide Y, 3-methoxy-4-hydroxyphenylethylene glycol and 5-hydroxy-indole acetic acid concentrations in patients with cerebral infarction". Drugs Under Experimental and Clinical Research. 21 (5): 175–80. PMID   8846747.
  2. ↑ Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 265. ISBN   978-0-412-46630-4.
  3. ↑ Shigemitsu T, Majima Y (1996). "Use of bifemelane hydrochloride in improving and maintaining the visual field of patients with glaucoma". Clinical Therapeutics. 18 (1): 106–13. doi:10.1016/S0149-2918(96)80183-4. PMID   8851457.
  4. ↑ Hayashi K, Hashimoto K, Yanagi M, Umeda T, Hama R (August 1998). "Drug approval in Japan questioned". Lancet. 352 (9126): 491. doi:10.1016/S0140-6736(05)79232-1. PMID   9708787.
  5. ↑ Naoi M, Nomura Y, Ishiki R, Suzuki H, Nagatsu T (January 1988). "4-(O-benzylphenoxy)-N-methylbutylamine (bifemelane) and other 4-(O-benzylphenoxy)-N-methylalkylamines as new inhibitors of type A and B monoamine oxidase". Journal of Neurochemistry. 50 (1): 243–7. doi:10.1111/j.1471-4159.1988.tb13256.x. PMID   3335842. S2CID   35543291.
  6. ↑ Kovel'man IR, Tochilkin AI, Gorkin VZ (1991). "Structure and action of reversible monoamine oxidase inhibitors (review)". Pharmaceutical Chemistry Journal. 25 (8): 505–520. doi:10.1007/BF00777412. ISSN   0091-150X. S2CID   42477788.
  7. ↑ Choe JY (4 March 2011). Drug Actions and Interactions. McGraw Hill Professional. p. 307. ISBN   978-0-07-176945-7.
  8. ↑ Dostert P (1994). "Can our knowledge of monoamine oxidase (MAO) help in the design of better MAO inhibitors?". Amine Oxidases: Function and Dysfunction. Vol. 41. pp. 269–279. doi:10.1007/978-3-7091-9324-2_35. ISBN   978-3-211-82521-1. PMID   7931236. For example, bifemelane [4-(O-benzylphenoxy)-N-methylbutylamine) is one of the few molecules in which both activities, reversible inhibition of MAO-A (Naoi et al., 1988) and inhibition of noradrenaline uptake (Egawa et al., 1983), although weak (IC50 = 10-6-10-7 M), coexist.{{cite book}}: |journal= ignored (help)
  9. ↑ Kondo Y, Ogawa N, Asanuma M, Matsuura K, Nishibayashi K, Iwata E (March 1996). "Preventive effects of bifemelane hydrochloride on decreased levels of muscarinic acetylcholine receptor and its mRNA in a rat model of chronic cerebral hypoperfusion". Neuroscience Research. 24 (4): 409–14. doi:10.1016/0168-0102(95)01017-3. PMID   8861111. S2CID   34313096.
  10. ↑ Egashira T, Takayama F, Yamanaka Y (September 1996). "Effects of bifemelane on muscarinic receptors and choline acetyltransferase in the brains of aged rats following chronic cerebral hypoperfusion induced by permanent occlusion of bilateral carotid arteries". Japanese Journal of Pharmacology. 72 (1): 57–65. doi: 10.1254/jjp.72.57 . PMID   8902600.
  11. ↑ Moryl E, Danysz W, Quack G (June 1993). "Potential antidepressive properties of amantadine, memantine and bifemelane". Pharmacology & Toxicology. 72 (6): 394–7. doi:10.1111/j.1600-0773.1993.tb01351.x. PMID   8361950.
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