ADL-5747

Last updated
ADL-5747
ADL-5747.svg
Names
IUPAC name
N,N-diethyl-3-hydroxy-4-spiro[chromene-2,4'-piperidine]-4-ylbenzamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C24H28N2O3/c1-3-26(4-2)23(28)17-9-10-18(21(27)15-17)20-16-24(11-13-25-14-12-24)29-22-8-6-5-7-19(20)22/h5-10,15-16,25,27H,3-4,11-14H2,1-2H3
    Key: ALGHKWSXJUQNJJ-UHFFFAOYSA-N
  • CCN(CC)C(=O)C1=CC(=C(C=C1)C2=CC3(CCNCC3)OC4=CC=CC=C42)O
Properties
C24H28N2O3
Molar mass 392.499 g·mol−1
Related compounds
Related compounds
 ADL-5859
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

ADL-5747 was a novel opioid analgesic drug, however its development was halted because it did not pass phase II trials. [1]

Mechanism of action

ADL-5747 is an opioid analgesic, it works by activating opioid receptors. However, unlike "classical" opioids such as morphine, it is selective for the delta receptor. [2]

In tests done on mice, ADL-5747 was able to reduce pain in an efficient way. This compound does not seem to cause receptor internalization. [2]

References

  1. ↑ Spahn, Viola; Stein, Christoph (February 2017). "Targeting delta opioid receptors for pain treatment: drugs in phase I and II clinical development". Expert Opinion on Investigational Drugs. 26 (2): 155–160. doi:10.1080/13543784.2017.1275562. ISSN   1744-7658. PMID   28001096. S2CID   22258505.
  2. 1 2 Nozaki, Chihiro; Le Bourdonnec, Bertrand; Reiss, David; Windh, Rolf T.; Little, Patrick J.; Dolle, Roland E.; Kieffer, Brigitte L.; Gavériaux-Ruff, Claire (September 2012). "δ-Opioid mechanisms for ADL5747 and ADL5859 effects in mice: analgesia, locomotion, and receptor internalization". The Journal of Pharmacology and Experimental Therapeutics. 342 (3): 799–807. doi:10.1124/jpet.111.188987. ISSN   1521-0103. PMC   3422521 . PMID   22700431.
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