SKF-83566   Click here for help

GtoPdb Ligand ID: 944

Synonyms: SK&F-83566 | SK-83566 | SK83566
Compound class: Synthetic organic
Comment: SKF-83566 is a dopamine receptor antagonist with selectivity for D1/D5 compared to D2 [1,3].
Note we have corrected the name of this ligand from SKF-83556 to SKF-83566.
SKF-83566 (30 μM) is reported to inhibit adenylyl cyclase 2 (AC2) activity by ~95% in vitro [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 23.47
Molecular weight 331.06
XLogP 3.66
No. Lipinski's rules broken 0
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Canonical SMILES CN1CCc2c(C(C1)c1ccccc1)cc(c(c2)Br)O
Isomeric SMILES CN1CCc2c(C(C1)c1ccccc1)cc(c(c2)Br)O
InChI InChI=1S/C17H18BrNO/c1-19-8-7-13-9-16(18)17(20)10-14(13)15(11-19)12-5-3-2-4-6-12/h2-6,9-10,15,20H,7-8,11H2,1H3
1. Bakthavachalam V, Baindur N, Madras BK, Neumeyer JL. (1991)
Fluorescent probes for dopamine receptors: synthesis and characterization of fluorescein and 7-nitrobenz-2-oxa-1,3-diazol-4-yl conjugates of D-1 and D-2 receptor ligands.
J Med Chem, 34 (11): 3235-41. [PMID:1956042]
2. Conley JM, Brand CS, Bogard AS, Pratt EP, Xu R, Hockerman GH, Ostrom RS, Dessauer CW, Watts VJ. (2013)
Development of a high-throughput screening paradigm for the discovery of small-molecule modulators of adenylyl cyclase: identification of an adenylyl cyclase 2 inhibitor.
J Pharmacol Exp Ther, 347 (2): 276-87. [PMID:24008337]
3. Sunahara RK, Guan HC, O'Dowd BF, Seeman P, Laurier LG, Ng G, George SR, Torchia J, Van Tol HH, Niznik HB. (1991)
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
Nature, 350 (6319): 614-9. [PMID:1826762]