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Azaprocin

Opioid analgesic drug

Opioid analgesic drug

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Azaprocin is a drug which is an opioid analgesic with approximately ten times the potency of morphine, and a fast onset and short duration of action. It was discovered in 1963, but has never been marketed.

Para-nitroazaprocin, the derivative substituted on the phenyl ring with a p-nitro group, is more potent than the parent compound, around 25× the potency of morphine. The ring-opened 2,6-dimethylpiperazine analogues are also active, and a large family of opioid analgesic compounds derived from this parent structure have been developed over the last 40 years. One analogue, AP-237, has been used in China to treat the pain caused by cancer.

References

References

  1. (November 1963). "Bicyclic Homologs of Piperazine. VI.1Synthesis and Analgesic Activity of 3-Substituted 8-Propionyl-3,8-diazabicyclo[3.2.1]octanes". Journal of Medicinal Chemistry.
  2. (May 1965). "Bicyclic Homologs of Piperazine. VII.1Synthesis and Analgesic Activity of 3-Aralkenyl-8-propionyl-3,8-diazabicyclo[3.2.1]octanes". Journal of Medicinal Chemistry.
  3. (February 1968). "[Effect of analgesic drugs on the conditioned behavior of rats]". Bollettino Chimico Farmaceutico.
  4. (May 1988). "Interaction of 3,8-diazabicyclo (3.2.1) octanes with mu and delta opioid receptors". Pharmacological Research Communications.
  5. (May 1968). "2,6-Dialkylpiperazines. IV. 1-Propionyl-4-substituted cis-2,6-dimethylpiperazines structurally related to the analgetic 8-acyl-3,8-diazabicyclo[3.2.1]octanes". Journal of Medicinal Chemistry.
  6. (May 1988). "Interaction of 3,8-diazabicyclo (3.2.1) octanes with mu and delta opioid receptors". Pharmacological Research Communications.
  7. (October 1993). "Computer-aided structure-affinity relationships in a set of piperazine and 3,8-diazabicyclo[3.2.1]octane derivatives binding to the mu-opioid receptor". Journal of Computer-Aided Molecular Design.
  8. (November 1997). "Antinociceptive action of DBO 17 and DBO 11 in mice: two 3,8 diazabicyclo (3.2.1.) octane derivates with selective mu opioid receptor affinity". Naunyn-Schmiedeberg's Archives of Pharmacology.
  9. (1998). "Synthesis and mu-opioid receptor affinity of a new series of nitro substituted 3,8-diazabicyclo[3.2.1]octane derivatives". Farmaco.
  10. (1998). "Benzocondensed derivatives as rigid analogues of the mu-opioid agonist 3(8)-cinnamyl-8(3)-propionyl-3,8-diazabicyclo[3.2.1]octanes: synthesis, modeling, and affinity". Farmaco.
  11. (June 2000). "Synthesis, molecular modeling, and opioid receptor affinity of 9, 10-diazatricyclo[4.2.1.1(2,5)]decanes and 2,7-diazatricyclo[4.4.0. 0(3,8)]decanes structurally related to 3,8-diazabicyclo[3.2. 1]octanes". Journal of Medicinal Chemistry.
  12. (August 2000). "Synthesis, modelling, and mu-opioid receptor affinity of N-3(9)-arylpropenyl-N-9(3)-propionyl-3,9-diazabicycl". Farmaco.
  13. (June 2002). "N-3(9)-arylpropenyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes as mu-opioid receptor agonists. Effects on mu-affinity of arylalkenyl chain modifications". Bioorganic & Medicinal Chemistry.
  14. (September 2003). "Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3' allyl end and at the phenyl ring of the cinnamyl chain on mu-receptor affinity and opioid antinociception". Bioorganic & Medicinal Chemistry.
  15. (February 2006). "Synthesis of 3,6-diazabicyclo[3.1.1]heptanes as novel ligands for the opioid receptors". Bioorganic & Medicinal Chemistry.
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synthetic-opioids propionamides alkene-derivatives piperazines mu-opioid-receptor-agonists phenyl-compounds
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