ADL-5747
{{Chembox
| ImageFile = ADL-5747.svg
| IUPACName = N,N-diethyl-3-hydroxy-4-spiro[chromene-2,4'-piperidine]-4-ylbenzamide
| Section1 = {{Chembox Identifiers
| CASNo = 850176-30-6
| CASNo_Comment = (freebase)
| CASNo1 = 1187653-56-0
| CASNo1_Comment = (hydrochloride)
| ChEMBL = 561339
| ChemSpiderID = 9375258
| IUPHAR_ligand = 9003
| PubChem = 11200189
| UNII = BRJ718SA03
| SMILES = CCN(CC)C(=O)C1=CC(=C(C=C1)C2=CC3(CCNCC3)OC4=CC=CC=C42)O
| 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
| InChIKey = ALGHKWSXJUQNJJ-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
|C=24 |H=28 |N=2 |O=3
}}
|Section8={{Chembox Related
| OtherCompounds = ADL-5859
}}
}}
ADL-5747 was a novel opioid analgesic drug, however its development was halted because it did not pass phase II trials.{{Cite journal |last1=Spahn |first1=Viola |last2=Stein |first2=Christoph |date=February 2017 |title=Targeting delta opioid receptors for pain treatment: drugs in phase I and II clinical development |url=https://pubmed.ncbi.nlm.nih.gov/28001096/ |journal=Expert Opinion on Investigational Drugs |volume=26 |issue=2 |pages=155–160 |doi=10.1080/13543784.2017.1275562 |issn=1744-7658 |pmid=28001096|s2cid=22258505 }}
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.{{Cite journal |last1=Nozaki |first1=Chihiro |last2=Le Bourdonnec |first2=Bertrand |last3=Reiss |first3=David |last4=Windh |first4=Rolf T. |last5=Little |first5=Patrick J. |last6=Dolle |first6=Roland E. |last7=Kieffer |first7=Brigitte L. |last8=Gavériaux-Ruff |first8=Claire |date=September 2012 |title=δ-Opioid mechanisms for ADL5747 and ADL5859 effects in mice: analgesia, locomotion, and receptor internalization |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=342 |issue=3 |pages=799–807 |doi=10.1124/jpet.111.188987 |issn=1521-0103 |pmc=3422521 |pmid=22700431}}
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
{{Reflist}}
{{Opioid receptor modulators}}
Category:2-Hydroxyphenyl compounds