10-Ketonaltrexone and 10-ketooxymorphone.

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Archer S, Seyed-Mozaffari A, Ward S, Kosterlitz HW, Paterson SJ, McKnight AT, Corbett AD

10-Ketonaltrexone and 10-ketooxymorphone.

J Med Chem. 1985 Jul;28(7):974-6.

PubMed ID

2409281 [ View in PubMed

]

Abstract

Ethylketocyclazocine (1) has greater kappa/mu selectivity than cyclazocine in brain binding assays. 10-Ketonaltrexone (11) and 10-ketooxymorphone (10) were prepared from naltrexone 3-methyl ether and oxycodone, respectively. Bioassays in the myenteric plexus longitudinal muscle preparation of the guinea pig ileum and in the mouse vas deferens, in addition to brain binding assays, demonstrated that 10 and 11 were far less potent than naltrexone (2) and oxymorphone (3) at mu sites and also had little affinity for kappa and delta sites. It is concluded that introduction of the 10-keto group in naltrexone and oxymorphone diminished opioid effects at all binding sites.

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Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Oxymorphone	Mu-type opioid receptor	Ki (nM)	0.78	N/A	N/A	Details