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Bifemelane

From Wikipedia, the free encyclopedia
Antidepressant and cerebral activator drug

Pharmaceutical compound
Bifemelane
Clinical data
Trade namesAlnert, Celeport
Other namesMCl-2016, 4-(O-benzylphenoxy)-N-methylbutylamine
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • N-methyl-4-[2-(phenylmethyl)phenoxy]butan-1-amine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.220.566Edit this at Wikidata
Chemical and physical data
FormulaC18H23NO
Molar mass269.388 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 checkY
  • Key:QSQQPMHPCBLLGX-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Bifemelane (INN), sold under the brand namesAlnert andCeleport, is anantidepressant andcerebral activator that was widely used in the treatment ofcerebral infarction patients withdepressive symptoms in Japan, and in the treatment ofdementia as well.[1][2] It also appears to be useful in the treatment ofglaucoma.[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 amonoamine oxidase inhibitor (MAOI) of bothisoenzymes, with competitive reversible inhibition ofMAO-A (Ki = 4.20 μM), making it areversible inhibitor of monoamine oxidase A (RIMA) and non-competitive irreversible inhibition ofMAO-B (Ki = 46.0 μM),[5][6][7] and also acts (weakly) as anorepinephrine reuptake inhibitor (NRI).[8] The drug hasnootropic,neuroprotective, andantidepressant-like effects inanimal models, and appears to enhance thecholinergic system in thebrain.[9][10][11]

See also

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References

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  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.
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Miscellaneous
Psychoanaleptics: Anti-dementia agents (ATC codeN06D and others)
AChE inhibitor medications
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