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52994-23-7Relevant articles and documents
Metabolism of butyrylfentanyl in fresh human hepatocytes: Chemical synthesis of authentic metabolite standards for definitive identification
Kanamori, Tatsuyuki,Iwata, Yuko Togawa,Segawa, Hiroki,Yamamuro, Tadashi,Kuwayama, Kenji,Tsujikawa, Kenji,Inoue, Hiroyuki
, p. 623 - 630 (2019/05/08)
The metabolism of butyrylfentanyl, a new designer drug, was investigated using fresh human hepatocytes isolated from a liver-humanized mouse model. In the culture medium of hepatocytes incubated with butyrylfentanyl, the desphenethylated metabolite (nor-butyrylfentanyl), w-hydroxy-butyrylfentanyl, (w-1)-hydroxy-butyrylfentanyl, 4′-hydroxy-butyrylfentanyl, β-hydroxy-butyrylfentanyl, 4′-hydroxy-3′- methoxy-butyrylfentanyl, and w-carboxy-fentanyl were identified as the metabolites of butyrylfentanyl. Each metabolite was definitively identified by comparing the analytical data with those of authentic standards. The amount of the main metabolite, nor-butyrylfentanyl, reached 37% of the initial amount of butyrylfentanyl at 48 h. W-Hydroxy-butyrylfentanyl and (w-1)-hydroxy-butyrylfentanyl, formed by hydroxylation at the Nbutyryl group of butyrylfentanyl, were the second and third largest metabolites, respectively. The majority of 4′-hydroxy-butyrylfentanyl and 4′-hydroxy-3′-methoxy-butyrylfentanyl was considered to be conjugated. CYP reaction phenotyping for butyrylfentanyl using human liver microsomes and various anti-CYP antibodies revealed that CYP3A4 was involved in the formation of nor-butyrylfentanyl, (w-1)-hydroxybutyrylfentanyl, and β-hydroxy-butyrylfentanyl. In contrast, CYP2D6 was involved in the formation of w-hydroxy-butyrylfentanyl.
Designing and synthesis of novel amidated fentanyl analogs
Haghighatnia, Yaghoub,Balalaie, Saeed,Bijanzadeh, Hamid Reza
experimental part, p. 818 - 824 (2012/06/16)
Some new amidated fentanyl (=N-[1-(2-phenylethyl)piperidin-4-yl]-N- phenylpropanamide) analogs with a 4-(N-phenylamido)piperidine scaffold and additional amide bonds have been designed and synthesized through Ugi four-component reaction (Ugi-4CR). Good-to-high yields, diversity-oriented synthesis, and possible applications in drug discovery are advantages of this approach. Copyright
Development of novel enkephalin analogues that have enhanced opioid activities at both μ and δ opioid receptors
Yeon, Sun Lee,Petrov, Ravil,Park, Chad K.,Ma, Shou-Wu,Davis, Peg,Lai, Josephine,Porreca, Frank,Vardanyan, Ruben,Hruby, Victor J.
, p. 5528 - 5532 (2008/03/13)
Enkephalin analogues with a 4-anilidopiperidine scaffold have been designed and synthesized to achieve therapeutic benefit for the treatment of pain due to mixed μ and δ opioid agonist activities. Ligand 16, in which a Dmt-substituted enkephalin-like stru