apabetalone   Click here for help

GtoPdb Ligand ID: 7034

Synonyms: QC-216 | RVX 208 | RVX-000222 | RVX-208
PDB Ligand
Compound class: Synthetic organic
Comment: Apabetalone (RVX 208) is a derivative of the plant polyphenol resveratrol. RVX 208 is an investigational inhibitor of BET bromodomain containing proteins, with potential anti-atherosclerotic action for the treatment of cardiovascular disease (CVD) [3-4].

SARS-CoV-2 and CIVID-19: Apabetalone (RVX 208) has been reported to reduce ACE2 expression and hence SARS-CoV-2 infection in vitro [2], and to block inflammation-mediated cardiac injury and dysfunction that is caused by SARS-CoV-2 infection (in a study using human cardiac organoids) [6]. It has been respositioned for potential to provide a cardio-protective therapy that prevents COVID-19-mediated cardiac damage.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 93.67
Molecular weight 370.15
XLogP 3.86
No. Lipinski's rules broken 0
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Canonical SMILES OCCOc1c(C)cc(cc1C)c1nc(=O)c2c([nH]1)cc(cc2OC)OC
Isomeric SMILES OCCOc1c(C)cc(cc1C)c1nc(=O)c2c([nH]1)cc(cc2OC)OC
InChI InChI=1S/C20H22N2O5/c1-11-7-13(8-12(2)18(11)27-6-5-23)19-21-15-9-14(25-3)10-16(26-4)17(15)20(24)22-19/h7-10,23H,5-6H2,1-4H3,(H,21,22,24)
1. Bailey D, Jahagirdar R, Gordon A, Hafiane A, Campbell S, Chatur S, Wagner GS, Hansen HC, Chiacchia FS, Johansson J et al.. (2010)
RVX-208: a small molecule that increases apolipoprotein A-I and high-density lipoprotein cholesterol in vitro and in vivo.
J Am Coll Cardiol, 55 (23): 2580-9. [PMID:20513599]
2. Gilham D, Smith AL, Fu L, Moore DY, Muralidharan A, Reid SPM, Stotz SC, Johansson JO, Sweeney M, Wong NCW et al.. (2021)
Bromodomain and Extraterminal Protein Inhibitor, Apabetalone (RVX-208), Reduces ACE2 Expression and Attenuates SARS-Cov-2 Infection In Vitro.
Biomedicines, 9 (4): 437. [PMID:33919584]
3. Jahagirdar R, Zhang H, Azhar S, Tobin J, Attwell S, Yu R, Wu J, McLure KG, Hansen HC, Wagner GS et al.. (2014)
A novel BET bromodomain inhibitor, RVX-208, shows reduction of atherosclerosis in hyperlipidemic ApoE deficient mice.
Atherosclerosis, 236 (1): 91-100. [PMID:25016363]
4. McLure KG, Gesner EM, Tsujikawa L, Kharenko OA, Attwell S, Campeau E, Wasiak S, Stein A, White A, Fontano E et al.. (2013)
RVX-208, an inducer of ApoA-I in humans, is a BET bromodomain antagonist.
PLoS ONE, 8 (12): e83190. [PMID:24391744]
5. McNeill E. (2010)
RVX-208, a stimulator of apolipoprotein AI gene expression for the treatment of cardiovascular diseases.
Curr Opin Investig Drugs, 11 (3): 357-64. [PMID:20178050]
6. Mills RJ, Humphrey SJ, Fortuna PRJ, Lor M, Foster SR, Quaife-Ryan GA, Johnston RL, Dumenil T, Bishop C, Rudraraju R et al.. (2021)
BET inhibition blocks inflammation-induced cardiac dysfunction and SARS-CoV-2 infection.
Cell, 184 (8): 2167-2182.e22. [PMID:33811809]
7. Nicholls SJ, Gordon A, Johannson J, Ballantyne CM, Barter PJ, Brewer HB, Kastelein JJ, Wong NC, Borgman MR, Nissen SE. (2012)
ApoA-I induction as a potential cardioprotective strategy: rationale for the SUSTAIN and ASSURE studies.
Cardiovasc Drugs Ther, 26 (2): 181-7. [PMID:22349989]
8. Picaud S, Wells C, Felletar I, Brotherton D, Martin S, Savitsky P, Diez-Dacal B, Philpott M, Bountra C, Lingard H et al.. (2013)
RVX-208, an inhibitor of BET transcriptional regulators with selectivity for the second bromodomain.
Proc Natl Acad Sci USA, 110 (49): 19754-9. [PMID:24248379]