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.^[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

^ 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.
^ ^a ^b 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] 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]

[2]