Chemistry:BU72
From HandWiki
Short description: Opioid analgesic drug
 | |
| Identifiers | |
|---|---|
| |
| CAS Number | |
| PubChem CID | |
| IUPHAR/BPS | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| PDB ligand | |
| Chemical and physical data | |
| Formula | C28H32N2O2 |
| Molar mass | 428.576 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
BU72 is an extremely potent opioid, with one of the highest known affinities for the μ-opioid receptor. In animal studies, it was found to be a potent analgesic, with a slow onset and long duration of action, but was not considered suitable to develop for medical use.[1] It was used to produce the first crystal structure of the active μ-opioid receptor,[2] and is now widely used to model the activation process.[3][4][5] The stereochemistry has recently been revised, with the phenyl group in the (R) configuration,[6] which has been accepted by the authors of the crystal structure.[7]
BU72 original proposed structure ((S)-phenyl epimer)
See also
References
- ↑ "Characterization of the complex morphinan derivative BU72 as a high efficacy, long-lasting mu-opioid receptor agonist". European Journal of Pharmacology 499 (1–2): 107–16. September 2004. doi:10.1016/j.ejphar.2004.07.097. PMID 15363957.
- ↑ "Structural insights into µ-opioid receptor activation". Nature 524 (7565): 315–21. August 2015. doi:10.1038/nature14886. PMID 26245379. Bibcode: 2015Natur.524..315H.
- ↑ "Propagation of conformational changes during μ-opioid receptor activation". Nature 524 (7565): 375–8. August 2015. doi:10.1038/nature14680. PMID 26245377. Bibcode: 2015Natur.524..375S.
- ↑ "Computational insights into the G-protein-biased activation and inactivation mechanisms of the μ opioid receptor". Acta Pharmacologica Sinica 39 (1): 154–164. January 2018. doi:10.1038/aps.2017.158. PMID 29188799.
- ↑ "Ligand based conformational space studies of the μ-opioid receptor". Biochimica et Biophysica Acta (BBA) - General Subjects 1865 (3): 129838. December 2020. doi:10.1016/j.bbagen.2020.129838. PMID 33373630.
- ↑ "Revised (β-phenyl) stereochemistry of ultrapotent μ opioid BU72.". bioRxiv. April 2020. doi:10.1101/2020.04.01.020883.
- ↑ "Author Correction: Structural insights into μ-opioid receptor activation". Nature 584 (7820): E16. August 2020. doi:10.1038/s41586-020-2542-z. PMID 32724208.
 |  |
