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ADL-5747

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ADL-5747
Names
IUPAC name N,N-diethyl-3-hydroxy-4-spiro-4-ylbenzamide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
IUPHAR/BPS
PubChem CID
UNII
InChI
  • 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,3-4,11-14H2,1-2H3Key: ALGHKWSXJUQNJJ-UHFFFAOYSA-N
SMILES
  • CCN(CC)C(=O)C1=CC(=C(C=C1)C2=CC3(CCNCC3)OC4=CC=CC=C42)O
Properties
Chemical formula C24H28N2O3
Molar mass 392.499 g·mol
Related compounds
Related compounds ADL-5859
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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.

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.

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. ^ 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.
Opioid receptor modulators
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
  • Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
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