ADL-5747

ADL-5747
Names
	IUPAC name N,N-diethyl-3-hydroxy-4-spiro[chromene-2,4'-piperidine]-4-ylbenzamide
Identifiers
CAS Number	850176-30-6 (freebase); 1187653-56-0 (hydrochloride);
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL561339;
ChemSpider	9375258;
IUPHAR/BPS	9003;
PubChem CID	11200189;
UNII	BRJ718SA03;
	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,3-4,11-14H2,1-2H3 Key: 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−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). Infobox references

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

↑ 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.
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.

[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.

[:0-2] 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.