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Minaprine

From Wikipedia, the free encyclopedia
Chemical compound

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Pharmaceutical compound
Minaprine
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Eliminationhalf-life2-2.5 hours
Identifiers
  • 4-methyl-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.043.012Edit this at Wikidata
Chemical and physical data
FormulaC17H22N4O
Molar mass298.390 g·mol−1
3D model (JSmol)
  • CC1=CC(=NN=C1NCCN2CCOCC2)C3=CC=CC=C3
  • InChI=1S/C17H22N4O/c1-14-13-16(15-5-3-2-4-6-15)19-20-17(14)18-7-8-21-9-11-22-12-10-21/h2-6,13H,7-12H2,1H3,(H,18,20) checkY
  • Key:LDMWSLGGVTVJPG-UHFFFAOYSA-N checkY

Minaprine (INN,USAN,BAN; brand namesBrantur,Cantor) is amonoamine oxidase inhibitorantidepressant drug that was used inFrance for the treatment ofdepression until it waswithdrawn from the market in 1996 because it causedconvulsions.[2][3]

A study found that it acts as areversible inhibitor of MAO-A (RIMA) in rats.[4] It has also been found to weaklyinhibitacetylcholinesterase in rat brain (striatum) homogenates.[5]

It has demonstrated significant antibiotic activity againstM. chelonae andM. abscessus in tests withantibiotic resistant bacteria.[6]

Synthesis

[edit]

The first synthesis of minaprine was disclosed in patents published in 1979.[7]

The final step is the reaction between a chloro-substitutedpyridazine and theprimary amine group of amorpholine derivative.[7][8] The required pyridazine can be made by the reaction ofacetophenone andpyruvic acid, followed by ring formation usinghydrazine, giving a pyrazidinone. Treatment of this withphosphoryl chloride converts it to the required chloro derivative.[2]

References

[edit]
  1. ^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-16.
  2. ^abWermuth CG, Schlewer G, Bourguignon JJ, Maghioros G, Bouchet MJ, Moire C, et al. (March 1989). "3-aminopyridazine derivatives with atypical antidepressant, serotonergic, and dopaminergic activities".Journal of Medicinal Chemistry.32 (3):528–537.doi:10.1021/jm00123a004.PMID 2563772.
  3. ^Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E (1 January 2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999".Therapeutic Innovation & Regulatory Science.35 (1):293–317.doi:10.1177/009286150103500134.S2CID 73036562.
  4. ^Kan JP, Mouget-Goniot C, Worms P, Biziere K (March 1986). "Effect of the antidepressant minaprine on both forms of monoamine oxidase in the rat".Biochemical Pharmacology.35 (6):973–978.doi:10.1016/0006-2952(86)90085-7.PMID 3954800.
  5. ^Contreras JM, Rival YM, Chayer S, Bourguignon JJ, Wermuth CG (February 1999). "Aminopyridazines as acetylcholinesterase inhibitors".Journal of Medicinal Chemistry.42 (4):730–741.doi:10.1021/jm981101z.PMID 10052979.
  6. ^Chopra S, Matsuyama K, Hutson C, Madrid P (July 2011)."Identification of antimicrobial activity among FDA-approved drugs for combating Mycobacterium abscessus and Mycobacterium chelonae".The Journal of Antimicrobial Chemotherapy.66 (7):1533–1536.doi:10.1093/jac/dkr154.PMID 21486854.
  7. ^abUS patent 4169158, Henri Laborit, "Pyridazine derivatives in alleviating depressive states", issued 1979-09-25, assigned to CM Industries, SA 
  8. ^"Minaprine".Pharmaceutical Substances. Thieme. Retrieved2024-07-21.
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
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine,epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-hydroxylase
PNMTTooltip Phenylethanolamine N-methyltransferase
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin,melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
Histamine
HDCTooltip Histidine decarboxylase
HNMTTooltip Histamine N-methyltransferase
DAOTooltip Diamine oxidase
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