Chemistry:SU-11739

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SU-11739 (other developmental code names AGN-1133, J-508; also known as N-methyl-N-propargyl-1-aminoindane)[1] is an experimental monoamine oxidase inhibitor (MAOI) that was never marketed.[2][3][4][5]

It is a dual or non-selective irreversible monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) inhibitor, with preference for inhibition of MAO-B over MAO-A.[3][4] It is less selective for MAO-B inhibition than AGN-1135 (racemic rasagiline) or rasagiline.[3] In addition to its MAOI activity, SU-11739 has been reported to have strong activity as a catecholamine releasing agent.[6] Similarly to rasagiline, but unlike selegiline and desmethylselegiline, SU-11739 is not a monoaminergic activity enhancer (MAE).[5][7]

The drug is the racemic N-methylated analogue of rasagiline.[2][3][4] It is also a ring-cyclized analogue of pargyline with about 20 times the MAOI potency of pargyline.[8]

SU-11739 was discovered before rasagiline and was patented in 1965.[9]

References

  1. ↑ "The enzyme-activated irreversible inhibition of type-B monoamine oxidase by 3-(4-[(3-chlorophenyl)methoxyphenyl)-5-[(methylamino) methyl]-2-oxazolidinone methanesulphonate (compound MD 780236) and the enzyme-catalysed oxidation of this compound as competing reactions"]. Biochem J 209 (1): 235–242. January 1983. doi:10.1042/bj2090235. PMID 6847610. "Clorgyline hydrochloride was a gift from May and Baker, Dagenham, Essex, U.K. L-Deprenyl hydrochloride and compound J-508 [N-methyl-N-propargyl-L-aminoindane hydrochloride (compound AGN 1133; compound Su-11739)] were gifts from Professor J. Knoll, Department of Pharmacology, Semmelweis University of Medicine, Budapest, Hungary.". 
  2. ↑ 2.0 2.1 "The discovery and development of rasagiline as a new anti-Parkinson medication". Journal of Neural Transmission 127 (2): 125–130. February 2020. doi:10.1007/s00702-020-02142-w. PMID 31974721. 
  3. ↑ 3.0 3.1 3.2 3.3 "Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity". Progress in Neurobiology 92 (3): 330–344. November 2010. doi:10.1016/j.pneurobio.2010.06.008. PMID 20600573. 
  4. ↑ 4.0 4.1 4.2 "Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness". British Journal of Pharmacology 147 (Suppl 1): S287–S296. January 2006. doi:10.1038/sj.bjp.0706464. PMID 16402116. 
  5. ↑ 5.0 5.1 "Essential difference between the pharmacological spectrum of (-)-deprenyl and rasagiline". Pharmacol Rep 66 (3): 453–458. June 2014. doi:10.1016/j.pharep.2013.11.003. PMID 24905523. 
  6. ↑ "(-)-deprenil, az N-metilprogargilamin-1-aminoindan (J-508) és a J-508 dezmetil analógjának (rasagilin) összehasonlító farmakológiai analízise" (in Hungarian). Neuropsychopharmacol Hung 10 (1): 15–22. March 2008. PMID 18771016. https://mppt.hu/magazin/pdf/x-evfevfolyam-1-szam/a---deprenil-az-n.pdf. 
  7. ↑ "The aphrodisiac effect of low doses of (-) deprenyl in male rats". Pol J Pharmacol Pharm 34 (5–6): 303–308. 1982. PMID 6821215. 
  8. ↑ "N-methyl-n-2-propynyl-l-indanamine. A protent monoamine oxidase inhibitor". Journal of Medicinal Chemistry 9 (6): 830–832. November 1966. doi:10.1021/jm00324a009. PMID 5972038. 
  9. ↑ Huebner CF, US patent 3201470, issued 17 August 1965




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